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Vanillin
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Monoaromatic
- Subclass: Benzoic Acid Derivative
| Canonical Smiles | COc1cc(C=O)ccc1O |
|---|---|
| InChI | InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3 |
| InChIKey | MWOOGOJBHIARFG-UHFFFAOYSA-N |
| Formula | C8H8O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 152.15 |
| Rotatable Bonds | 2 |
| TPSA | 46.53 |
| LogP | 1.21 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.12 |
| Exact Mass | 152.05 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Anastatica hierochuntica | Cruciferae-Brassicaceea | Plantae | 663965 |
| 2 | Xanthium spinosum | Asteraceae | Plantae | 1053410 |
| 3 | Euphorbia quinquecostata | Euphorbiaceae | Plantae | 3990 |
| 4 | Haloxylon scoparium | Chenopodiaceae | Plantae | 1665493 |
Showing of synonyms
Vanillin
121-33-5
Vanillaldehyde
Vanillic aldehyde
P-Vanillin
Lioxin
Vanilline
3-Methoxy-4-hydroxybenzaldehyde
4-Hydroxy-m-anisaldehyde
2-Methoxy-4-formylphenol
Zimco
P-Hydroxy-m-methoxybenzaldehyde
Methylprotocatechuic aldehyde
4-Formyl-2-methoxyphenol
Vanillin (natural)
4-Hydroxy-5-methoxybenzaldehyde
M-Anisaldehyde, 4-hydroxy-
Protocatechualdehyde, methyl-
FEMA No. 3107
Vaniline
Rhovanil
Protocatechualdehyde 3-methyl ether
NSC 15351
CCRIS 2687
Vanillin Melting Point Standard
HSDB 1027
Vanillin, natural
EINECS 204-465-2
NSC-15351
NSC-48383
NSC-403658
UNII-CHI530446X
BRN 0472792
M-Methoxy-p-hydroxybenzaldehyde
CHEBI:18346
4-hydroxy-3-methoxy-benzyldehyde
AI3-00093
NPLC-0145
CHI530446X
EC 204-465-2
H-0264
4-08-00-01763 (Beilstein Handbook Reference)
NSC15351
VANILLIN (II)
VANILLIN [II]
VANILLIN (MART.)
VANILLIN [MART.]
VANILLIN (EP MONOGRAPH)
VANILLIN [EP MONOGRAPH]
FEMA Number 3107
METHYLPROTOCATECHUALDEHYDE
204-465-2
4-Hydroxy-3-methoxybenzaldehyde
Vanilla
Benzaldehyde, 4-hydroxy-3-methoxy-
4-Hydroxy-3-methoxy-benzaldehyde
Vanilin
Vanillin (NF)
MFCD00006942
Vanillin [NF]
Vanillin (Standard)
CHEMBL13883
DTXSID0021969
Vanillin-13C
4-HYDROXY,3-METHOXY-BENZALDEHYDE
NCGC00091645-03
4-hydroxy-3-methoxybenzaldehyde (vanillin)
WLN: VHR DQ CO1
Vanillin [USAN]
DTXCID301969
Vanillinum
Oleoresin vanilla
Vanilla oleoresin
CAS-121-33-5
3-methoxy-4-hydroxy-benzaldehyde
Vanillin Essential
Vanillin ex Clove
Oleo-Resins vanilla
V55
Vanillin - natural
Vanillin sodium salt
Vanillin (Rhovanil)
Vanillin - synthetic
Vanillin (Rhovea(R))
VANILLIN [FHFI]
VANILLIN [HSDB]
Oleo-Resins vanilla-bean
VANILLIN [FCC]
VANILLIN [MI]
VANILLIN [VANDF]
Methyl-Protocatechualdehyde
Bmse000343
Bmse000597
Bmse010006
Methylprotcatechuic aldehyde
VANILLIN [USP-RS]
VANILLIN [WHO-DD]
SCHEMBL1213
Vanillin Nat Ex ferulic acid
MLS002303069
BIDD:ER0330
Vanillin, puriss., 99.5%
GTPL6412
SGCUT00016
4-hydroxy 3-methoxybenzaldehyde
HY-N0098R
Vanilla oleoresin (vanilla SPP)
3-methoxy-4-hydroxy benzaldehyde
4-hydroxy-3-methoxy benzaldehyde
VANILLIN, NATURAL [FHFI]
3-methoxy-4-hydroxy benzoaldehyde
Vanillin, ReagentPlus(R), 99%
4-hydroxy-3-(methoxy)benzaldehyde
HMS3651D20
HMS3885K07
Vanillin, >=97%, FCC, FG
4-hydoxy-3-(methyloxy)benzaldehyde
BCP29943
HY-N0098
LDA88484
NSC48383
STR01001
To_000089
Tox21_113534
Tox21_201925
Tox21_300352
4-hydoxy-3-(methyloxy)benz aldehyde
BBL011956
BDBM50177405
MFCD08702848
NSC403658
S3071
STK199262
AKOS000118929
Tox21_113534_1
CCG-266230
CS-W020052
FV09779
RP10096
Vanillin, tested according to Ph.Eur.
NCGC00091645-01
NCGC00091645-02
NCGC00091645-04
NCGC00091645-05
NCGC00091645-07
NCGC00254468-01
NCGC00259474-01
Vanillin, natural, >=97%, FCC, FG
AC-10370
BP-10602
FV156832
NCI60_001085
SMR000156285
SY224451
Vanillin 1000 microg/mL in Acetonitrile
Vanillin, JIS special grade, >=98.0%
Vanillin, Vetec(TM) reagent grade, 98%
3-Methoxy-4-hydroxybenzaldehyde (vanillin)
DB-003805
CS-0694801
H0264
NS00009754
SW219190-1
V0080
EN300-18281
Vanillin (3-methoxy-4-hydroxy- benzaldehyde)
C00755
D00091
Q33495
4-Hydroxy-3-methoxybenzaldehyde inclusion complex
Vanillin (83 degrees C) Melting Point Standard
4-hydroxy-3-methoxy-Benzaldehyde-5-chlorovanillin
4-hydroxy-3-methoxybenzaldehyde (ACD/Name 4.0)
AC-907/21098004
BRD-K24258499-001-05-8
Vanillin, TraceCERT(R), certified reference material
Z57772449
F2190-0587
Vanillin, European Pharmacopoeia (EP) Reference Standard
Mettler-Toledo Calibration substance ME 51143093, Vanillin
Vanillin, United States Pharmacopeia (USP) Reference Standard
NSC15351 pound>>4-Hydroxy-3-methoxybenzaldehyde
Vanillin, Pharmaceutical Secondary Standard
Certified Reference Material
InChI=1/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H
Vanillin Melting Point Standard, United States Pharmacopeia (USP) Reference Standard
Mettler-Toledo Calibration substance ME 51143093, Vanillin, traceable to primary standards (LGC)
Vanillin melting point standard, Pharmaceutical Secondary Standard
- Lachkar N, Lamchouri F, et al. (2021). Chemical composition, phenolic content and antioxidant capacity of Haloxylon scoparium extracts. Evidence-based complementary and alternative medicine : eCAM, 2021, 2021, 9011168. [View] [PubMed]
- Nakashima S, Matsuda H, et al. (2010). Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Bioorganic and Medicinal Chemistry,2010,18(6),2337-2345. [View] [PubMed]
- Su BN, Park EJ, et al. (2002). New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes.. Journal of Natural Products,2002,65(9),1278-1282. [View] [PubMed]
- Abdei-Mogib M, Dawidar AM, et al. (1991). Xanthanolides from Xanthium spinosum. Phytochemistry,1991,30(10),3461-3462. [View]
Pubchem:
1183
Cas:
121-33-5
Gnps:
CCMSLIB00005756101
Zinc:
ZINC000002567933
Kegg Ligand:
C00755
Chebi:
18346
Nmrshiftdb2:
10008648
Metabolights:
MTBLC18346
Chembl:
CHEMBL13883
Comptox:
DTXSID0021969
Pdb Ligand:
V55
Bindingdb:
50177405
Selleck:
vanillin
CPRiL:
23434
SMILES: c1ccccc1
Level: 0
Mol. Weight: 152.15 g/mol
Quinone reductase-inducing
Absorption
- Caco-2 (logPapp)
- -4.36
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.980
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.51
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.240
- Plasma Protein Binding
- 23.76
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.460
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.140
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Toxic
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.130
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.900
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 3.250
- Rat (Acute)
- 1.960
- Rat (Chronic Oral)
- 1.970
- Fathead Minnow
- 3.910
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 271.020
- Hydration Free Energy
- -8.560
- Log(D) at pH=7.4
- 1.090
- Log(P)
- 1.14
- Log S
- -1.62
- Log(Vapor Pressure)
- -3.06
- Melting Point
- 86.07
- pKa Acid
- 7.74
- pKa Basic
- 0.58
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.9695 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.9695 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.9532 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.9532 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9521 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9521 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9506 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9506 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9470 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9470 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9466 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9466 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9421 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9421 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9290 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9290 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.9219 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.9219 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9185 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9185 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.9118 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.9118 |
| Glycogenin-1 | P46976 | GLYG_HUMAN | Homo sapiens | 3 | 0.9115 |
| Glycogenin-1 | P46976 | GLYG_HUMAN | Homo sapiens | 3 | 0.9115 |
| S-norcoclaurine synthase | Q67A25 | NCS_THLFG | Thalictrum flavum subsp. glaucum | 3 | 0.9035 |
| S-norcoclaurine synthase | Q67A25 | NCS_THLFG | Thalictrum flavum subsp. glaucum | 3 | 0.9035 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8928 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8928 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8802 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8802 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8791 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8791 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8774 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8774 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8680 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8680 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8654 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8654 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8622 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8622 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8581 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8581 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8532 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8532 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8516 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8516 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.8328 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.8328 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8303 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8303 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8272 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8272 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8235 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8235 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8224 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8224 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8095 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8095 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.8002 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.8002 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7896 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7896 |
| Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.7860 |
| Glycogen synthase | P0A6U8 | GLGA_ECOLI | Escherichia coli | 3 | 0.7860 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7826 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7826 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7643 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7643 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7613 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7613 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7612 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7612 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7601 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7601 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7587 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7587 |
| Peroxidase C1A | P00433 | PER1A_ARMRU | Armoracia rusticana | 2 | 0.7559 |
| Peroxidase C1A | P00433 | PER1A_ARMRU | Armoracia rusticana | 2 | 0.7559 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7541 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7541 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7513 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7513 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7491 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7491 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7483 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7483 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7469 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7469 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7465 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7465 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7462 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7462 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7459 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7459 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7453 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7453 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7439 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7439 |
| ATP-dependent protease subunit HslV | P0A7B8 | HSLV_ECOLI | Escherichia coli | 3 | 0.7419 |
| ATP-dependent protease subunit HslV | P0A7B8 | HSLV_ECOLI | Escherichia coli | 3 | 0.7419 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7418 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7418 |
| N-glycosylase/DNA lyase | O15527 | OGG1_HUMAN | Homo sapiens | 3 | 0.7416 |
| N-glycosylase/DNA lyase | O15527 | OGG1_HUMAN | Homo sapiens | 3 | 0.7416 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7410 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7410 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7402 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7402 |
| Ceramide transfer protein | Q9Y5P4 | CERT_HUMAN | Homo sapiens | 2 | 0.7388 |
| Ceramide transfer protein | Q9Y5P4 | CERT_HUMAN | Homo sapiens | 2 | 0.7388 |
| 16S rRNA (adenine(1408)-N(1))-methyltransferase | A8C927 | NPMA_ECOLX | Escherichia coli | 3 | 0.7382 |
| 16S rRNA (adenine(1408)-N(1))-methyltransferase | A8C927 | NPMA_ECOLX | Escherichia coli | 3 | 0.7382 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7374 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7374 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7364 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7364 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7362 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7362 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7354 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7354 |
| Ribosomal RNA small subunit methyltransferase Nep1 | Q57977 | NEP1_METJA | Methanocaldococcus jannaschii | 3 | 0.7348 |
| Ribosomal RNA small subunit methyltransferase Nep1 | Q57977 | NEP1_METJA | Methanocaldococcus jannaschii | 3 | 0.7348 |
| cGMP-dependent protein kinase 1 | P00516 | KGP1_BOVIN | Bos taurus | 3 | 0.7343 |
| cGMP-dependent protein kinase 1 | P00516 | KGP1_BOVIN | Bos taurus | 3 | 0.7343 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7338 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7338 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7329 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7329 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7325 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7325 |
| Histidine kinase 4 | Q9C5U0 | AHK4_ARATH | Arabidopsis thaliana | 3 | 0.7317 |
| Histidine kinase 4 | Q9C5U0 | AHK4_ARATH | Arabidopsis thaliana | 3 | 0.7317 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7315 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7315 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7315 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7315 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7313 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7313 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7303 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7303 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7285 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7285 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7245 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7245 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7244 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7244 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7241 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7241 |
| histone deacetylase | A5H660 | A5H660_SCHMA | Schistosoma mansoni | 3 | 0.7235 |
| histone deacetylase | A5H660 | A5H660_SCHMA | Schistosoma mansoni | 3 | 0.7235 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7231 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7231 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7229 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7229 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 2 | 0.7228 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 2 | 0.7228 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7218 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7218 |
| chitinase | B0Y2Y2 | B0Y2Y2_ASPFC | Aspergillus fumigatus | 3 | 0.7218 |
| chitinase | B0Y2Y2 | B0Y2Y2_ASPFC | Aspergillus fumigatus | 3 | 0.7218 |
| tRNA (guanine-N(1)-)-methyltransferase | Q2GIL5 | TRMD_ANAPZ | Anaplasma phagocytophilum | 3 | 0.7217 |
| tRNA (guanine-N(1)-)-methyltransferase | Q2GIL5 | TRMD_ANAPZ | Anaplasma phagocytophilum | 3 | 0.7217 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7215 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7215 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7210 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7210 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 2 | 0.7209 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 2 | 0.7209 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7208 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7208 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7205 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7205 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7197 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7197 |
| Histone-lysine N-methyltransferase EHMT2 | Q96KQ7 | EHMT2_HUMAN | Homo sapiens | 3 | 0.7191 |
| Histone-lysine N-methyltransferase EHMT2 | Q96KQ7 | EHMT2_HUMAN | Homo sapiens | 3 | 0.7191 |
| Transitional endoplasmic reticulum ATPase | P55072 | TERA_HUMAN | Homo sapiens | 3 | 0.7189 |
| Transitional endoplasmic reticulum ATPase | P55072 | TERA_HUMAN | Homo sapiens | 3 | 0.7189 |
| Adenylosuccinate synthetase isozyme 1 | P28650 | PURA1_MOUSE | Mus musculus | 4 | 0.7186 |
| Adenylosuccinate synthetase isozyme 1 | P28650 | PURA1_MOUSE | Mus musculus | 4 | 0.7186 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7181 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7181 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7180 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7180 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7171 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7171 |
| Histone-lysine N-methyltransferase 2C | Q8NEZ4 | KMT2C_HUMAN | Homo sapiens | 3 | 0.7148 |
| Histone-lysine N-methyltransferase 2C | Q8NEZ4 | KMT2C_HUMAN | Homo sapiens | 3 | 0.7148 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7138 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 3 | 0.7138 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7133 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7133 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7130 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7130 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7128 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7128 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7123 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7123 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7120 |
| Histone-lysine N-methyltransferase 2A | Q03164 | KMT2A_HUMAN | Homo sapiens | 3 | 0.7120 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7117 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7117 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7111 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7111 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7109 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7109 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7107 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7107 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.7104 |
| SKP1-like protein 1A | Q39255 | SKP1A_ARATH | Arabidopsis thaliana | 3 | 0.7104 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 2 | 0.7098 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 2 | 0.7098 |
| cAMP-dependent protein kinase catalytic subunit alpha | P05132 | KAPCA_MOUSE | Mus musculus | 2 | 0.7092 |
| cAMP-dependent protein kinase catalytic subunit alpha | P05132 | KAPCA_MOUSE | Mus musculus | 2 | 0.7092 |
| Pyridoxal kinase | O00764 | PDXK_HUMAN | Homo sapiens | 2 | 0.7085 |
| Pyridoxal kinase | O00764 | PDXK_HUMAN | Homo sapiens | 2 | 0.7085 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7085 |
| Rho family GTPase | C4M4W4 | C4M4W4_ENTHI | Entamoeba histolytica | 4 | 0.7085 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7085 |
| Rho family GTPase | C4M4W4 | C4M4W4_ENTHI | Entamoeba histolytica | 4 | 0.7085 |
| Cytochrome b-c1 complex subunit 1, mitochondrial | P31800 | QCR1_BOVIN | Bos taurus | 3 | 0.7083 |
| Cytochrome b-c1 complex subunit 1, mitochondrial | P31800 | QCR1_BOVIN | Bos taurus | 3 | 0.7083 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7082 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7082 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7079 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7079 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7077 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7077 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7076 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7076 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7076 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7076 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7065 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7065 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7065 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7065 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7060 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7060 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 3 | 0.7051 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 3 | 0.7051 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7047 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7047 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7043 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7043 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7023 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7023 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7023 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7023 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7016 |
| D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 2 | 0.7016 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7016 |
| D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 2 | 0.7016 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7009 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7009 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7009 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7009 |
| dTDP-4-dehydro-6-deoxyglucose 3-epimerase | Q5SFD1 | CHMJ_STRBI | Streptomyces bikiniensis | 3 | 0.7008 |
| dTDP-4-dehydro-6-deoxyglucose 3-epimerase | Q5SFD1 | CHMJ_STRBI | Streptomyces bikiniensis | 3 | 0.7008 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7006 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7006 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.7002 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.7002 |