Syringic acid - Compound Card

Syringic acid

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Syringic acid

Structure
Zoomed Structure
  • Family: Plantae - Loranthaceae
  • Kingdom: Plantae
  • Class: Monoaromatic
    • Subclass: Benzenoid
Canonical Smiles COc1cc(cc(c1O)OC)C(=O)O
InChI InChI=1S/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12)
InChIKey JMSVCTWVEWCHDZ-UHFFFAOYSA-N
Formula C9H10O5
HBA 4
HBD 2
MW 198.17
Rotatable Bonds 3
TPSA 75.99
LogP 1.11
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 198.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Balanites aegyptiaca Zygophyllaceae Plantae 886265
2 Moringa oleifera Moringaceae Plantae 3735
3 Monanthotaxis littoralis Annonaceae Plantae 2231816
4 Achyranthes aspera Amaranthaceae Plantae 240005
5 Globimetula dinklagei Loranthaceae Plantae 70883

Showing of synonyms

  • Sarker SD, Bartholomew B, et al. (2000). Alkaloids from Balanites aegyptiaca. Fitoterapia,2000,71(3),328-330. [View] [PubMed]
  • Clara C, Matasyoh JC, et al. (2013). Antifungal activity of Monathotaxis littoralis essential oil against mycotoxigenic fungi isolated from maize.. International Journal of Microbiology Research and Reviews,2013,2(6),103-109. [View] [PubMed]
  • Ndhlala AR, Ghebrehiwot HM, et al. (2015). Antimicrobial, anthelmintic activities and characterisation of functional phenolic acids of Achyranthes aspera linn.: a medicinal plant used for the treatment of wounds and Ringworm in East Africa.. Frontiers in pharmacology,2015,6,274. [View] [PubMed]
  • Mkounga P, Maza HL, et al. (2016). New lupan-type triterpenoids.. Zeitschrift fur Naturforschung. C, Journal of biosciences,2016, 71(11-12), 381-386. [View] [PubMed]
  • Manguro LO, Lemmen P. (2007). Phenolics of Moringa oleifera leaves.. Natural Product Research,2007,21(1),56-68. [View] [PubMed]
Pubchem: 10742
Kegg Ligand: C10833
Chebi: 68329
Nmrshiftdb2: 20040774
Metabolights: MTBLC68329
Chembl: CHEMBL1414
Pdb Ligand: IJP
Bindingdb: 50187132
CPRiL: 56536
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 198.17 g/mol

Antifungal

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.590
Plasma Protein Binding
23.97
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
12.130
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.700
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.750
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
2.540
Micronucleos
Safe
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
3.300
Rat (Acute)
1.950
Rat (Chronic Oral)
3.190
Fathead Minnow
3.830
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
317.020
Hydration Free Energy
-11.360
Log(D) at pH=7.4
-0.750
Log(P)
1.1
Log S
-2.13
Log(Vapor Pressure)
-5.39
Melting Point
195.17
pKa Acid
4.17
pKa Basic
2.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9528
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9528
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9519
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9519
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9507
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9507
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9484
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9484
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9447
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9447
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9421
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.9421
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9223
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9223
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9206
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9206
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.9077
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.9077
Carbonic anhydrase 5A, mitochondrial P23589 CAH5A_MOUSE Mus musculus 3 0.9074
Carbonic anhydrase 5A, mitochondrial P23589 CAH5A_MOUSE Mus musculus 3 0.9074
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9065
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9065
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9004
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9004
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8682
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8682
3-dehydroquinate dehydratase P9WPX7 AROQ_MYCTU Mycobacterium tuberculosis 3 0.8677
3-dehydroquinate dehydratase P9WPX7 AROQ_MYCTU Mycobacterium tuberculosis 3 0.8677
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8646
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8646
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8585
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8585
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8452
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8452
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8430
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8430
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8423
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8423
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8409
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8409
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.8301
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.8301
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.8292
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.8292
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8284
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8284
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8261
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8261
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.8246
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.8246
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8232
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8232
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8200
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8200
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8152
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8152
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8131
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8131
Shikimate dehydrogenase (NADP(+)) P56119 AROE_HELPY Helicobacter pylori 3 0.8054
Shikimate dehydrogenase (NADP(+)) P56119 AROE_HELPY Helicobacter pylori 3 0.8054
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7955
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7955
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7939
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7939
Orotate phosphoribosyltransferase P08870 PYRE_SALTY Salmonella typhimurium 4 0.7933
Orotate phosphoribosyltransferase P08870 PYRE_SALTY Salmonella typhimurium 4 0.7933
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7908
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7908
Pyridoxal kinase, putative C4LVZ4 C4LVZ4_ENTHI Entamoeba histolytica 3 0.7880
Pyridoxal kinase, putative C4LVZ4 C4LVZ4_ENTHI Entamoeba histolytica 3 0.7880
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7775
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7775
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7750
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7750
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7663
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7663
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7652
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7652
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7634
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7634
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7623
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7623
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7566
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7566
Chorismate pyruvate-lyase P26602 UBIC_ECOLI Escherichia coli 3 0.7524
Chorismate pyruvate-lyase P26602 UBIC_ECOLI Escherichia coli 3 0.7524
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7491
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7491
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7481
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7481
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7471
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7471
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7464
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7464
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7456
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7456
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7419
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7419
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 4 0.7414
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 4 0.7414
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7412
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7412
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7407
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7407
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7407
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7407
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7395
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7395
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.7329
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.7329
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7321
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7321
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7313
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7313
Adenylosuccinate synthetase isozyme 1 P28650 PURA1_MOUSE Mus musculus 4 0.7302
Adenylosuccinate synthetase isozyme 1 P28650 PURA1_MOUSE Mus musculus 4 0.7302
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7258
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7258
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7258
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7258
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7236
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7236
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7223
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7223
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7200
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7200
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7187
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7187
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7180
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7180
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7174
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7174
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7158
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7158
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7147
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7147
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7144
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7144
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7112
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7112
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.7094
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.7094
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7082
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7082
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7081
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7081
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7073
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7073
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7044
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7044
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7031
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7031
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7019
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7019

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