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Juglanin
- Family: Plantae - Myrtaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(cc1)O |
|---|---|
| InChI | InChI=1S/C20H18O10/c21-7-13-15(25)17(27)20(29-13)30-19-16(26)14-11(24)5-10(23)6-12(14)28-18(19)8-1-3-9(22)4-2-8/h1-6,13,15,17,20-25,27H,7H2/t13-,15-,17+,20-/m0/s1 |
| InChIKey | POQICXMTUPVZMX-UXYNSRGZSA-N |
| Formula | C20H18O10 |
| HBA | 10 |
| HBD | 6 |
| MW | 418.35 |
| Rotatable Bonds | 4 |
| TPSA | 170.05 |
| LogP | 0.39 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 418.09 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rubus rigidus | Rosaceae | Plantae | 59497 |
| 2 | Eugenia edulis | Myrtaceae | Plantae | 2729927 |
Showing of synonyms
Juglanin
5041-67-8
Euglanin
3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Juglanin?
Kaempferol 3-a-L-arabinofuranoside
4H-1-Benzopyran-4-one, 3-(alpha-L-arabinofuranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
3-((2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Kaempferol 3-I+--L-arabinofuranoside
Kaempferol-3-o-alpha-l-arabinofuranoside
Kaempferol 3-arabinofuranoside
3-(((2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
CHEMBL469440
SCHEMBL16618210
CHEBI:167534
HY-N3442
LMPK12111839
CS-7981
Kaempferol 3-O-alpha-L-arabinofuranoside
DA-54566
MS-27302
XJ161837
G14296
Q15720546
3-(alpha-L-Arabinofuranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Kaempferol-3-arabinofuranoside
5,7,4'-Trihydroxyflavone 3-?-L-arabinofuranoside
Kaempferol 3-O-?-L-arabinofuranoside
- Nguelefack TB, Mbakam FH, et al. (2011). A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis.. Archives of pharmacal research,2011, 34(4), 543-550. [View] [PubMed]
- Hussein S.A, Hashem A.N, et al. (2003). Polyoxygenated flavonoids from Eugenia edulis. Phytochemistry, 2003, 64(4), 883-9. [View] [PubMed]
Pubchem:
5318717
Cas:
5041-67-8
Zinc:
ZINC000033832091
Chebi:
167534
Nmrshiftdb2:
60022514
Chembl:
CHEMBL469440
CPRiL:
55781
SMILES: O1CCCC1Oc(c2=O)c(-c3ccccc3)oc(c24)cccc4
Level: 2
Mol. Weight: 418.35 g/mol
SMILES: O1CCCC1Oc(c2=O)coc(c23)cccc3
Level: 1
Mol. Weight: 418.35 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 418.35 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 418.35 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 418.35 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 418.35 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.43
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.400
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 0.99
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.970
- Plasma Protein Binding
- 84.46
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 11.670
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.860
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.100
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.650
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- -33.120
- Rat (Acute)
- 2.460
- Rat (Chronic Oral)
- 3.480
- Fathead Minnow
- 3.970
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 565.110
- Hydration Free Energy
- -8.090
- Log(D) at pH=7.4
- 0.970
- Log(P)
- 1.7
- Log S
- -4.17
- Log(Vapor Pressure)
- -10.36
- Melting Point
- 224.11
- pKa Acid
- 6.6
- pKa Basic
- 5.52
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9759 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9460 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.9347 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.9085 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.9008 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8933 |
| Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 6 | 0.8917 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8889 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8882 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.8829 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.8790 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8769 |
| Botulinum neurotoxin type A | P0DPI0 | BXA1_CLOBO | Clostridium botulinum | 3 | 0.8745 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8572 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8533 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8477 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8405 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8387 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8376 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8375 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.8340 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8319 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8317 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.8294 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 4 | 0.8289 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.8240 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8121 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8119 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8118 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.8077 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.8074 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8068 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7962 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7958 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7949 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7945 |
| Nucleoside 2-deoxyribosyltransferase | Q8RLY5 | Q8RLY5_LACHE | Lactobacillus helveticus | 3 | 0.7927 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7916 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7913 |
| Beta-glucuronidase | P05804 | BGLR_ECOLI | Escherichia coli | 3 | 0.7910 |
| Capsid protein VP1 | O56137 | O56137_9VIRU | Adeno-associated virus - 6 | 4 | 0.7882 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7826 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7810 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.7786 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7784 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7779 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7778 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7737 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7729 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7718 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 5 | 0.7636 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7635 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7578 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7575 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7570 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7568 |
| Orf1a polyprotein | Q692E5 | Q692E5_CVHSA | SARS coronavirus TJF | 3 | 0.7548 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7547 |
| Tubulin alpha-1B chain | P81947 | TBA1B_BOVIN | Bos taurus | 3 | 0.7541 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7506 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7496 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7456 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7446 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 4 | 0.7443 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7434 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7373 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7370 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7361 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7343 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7342 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7318 |
| Heat shock protein HSP 90-beta | P08238 | HS90B_HUMAN | Homo sapiens | 3 | 0.7308 |
| DNA topoisomerase 4 subunit B | H7C794 | PARE_ENTFA | Enterococcus faecalis | 3 | 0.7296 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7264 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7250 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7249 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7230 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7217 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.7216 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7212 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7209 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7185 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7100 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7099 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.7085 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7080 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7078 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7077 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7070 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7069 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.7062 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7059 |
| Beta-hexosaminidase | Q9KU37 | NAGZ_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7045 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7032 |
| Glutathione S-transferase F2 | P46422 | GSTF2_ARATH | Arabidopsis thaliana | 3 | 0.7029 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7026 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7023 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7004 |