1-O-vanilloyl-beta-D-glucose

Details

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Internal ID 52efaf60-825c-4975-b1dc-fba934ecd8c2
Taxonomy Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
IUPAC Name [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 4-hydroxy-3-methoxybenzoate
SMILES (Canonical) COC1=C(C=CC(=C1)C(=O)OC2C(C(C(C(O2)CO)O)O)O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
InChI InChI=1S/C14H18O9/c1-21-8-4-6(2-3-7(8)16)13(20)23-14-12(19)11(18)10(17)9(5-15)22-14/h2-4,9-12,14-19H,5H2,1H3/t9-,10-,11+,12-,14+/m1/s1
InChI Key YROOZUQRTLHXIO-DIACKHNESA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C14H18O9
Molecular Weight 330.29 g/mol
Exact Mass 330.09508215 g/mol
Topological Polar Surface Area (TPSA) 146.00 Ų
XlogP -0.70
Atomic LogP (AlogP) -1.64
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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1-O-(4-hydroxy-3-methoxybenzoyl)-beta-D-glucopyranose
Vanilloyl glucose
CHEBI:71512
C20470
1-O-(4-hydroxy-3-methoxybenzoyl)-beta-D-glucose
Q27139670
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 4-hydroxy-3-methoxybenzoate

2D Structure

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2D Structure of 1-O-vanilloyl-beta-D-glucose

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.7149 71.49%
Caco-2 - 0.8546 85.46%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.6648 66.48%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8669 86.69%
OATP1B3 inhibitior + 0.9586 95.86%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.9400 94.00%
P-glycoprotein inhibitior - 0.9389 93.89%
P-glycoprotein substrate - 0.9088 90.88%
CYP3A4 substrate + 0.5103 51.03%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8302 83.02%
CYP3A4 inhibition - 0.8632 86.32%
CYP2C9 inhibition - 0.8775 87.75%
CYP2C19 inhibition - 0.9154 91.54%
CYP2D6 inhibition - 0.9346 93.46%
CYP1A2 inhibition - 0.8980 89.80%
CYP2C8 inhibition + 0.6342 63.42%
CYP inhibitory promiscuity - 0.7229 72.29%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.7412 74.12%
Eye corrosion - 0.9872 98.72%
Eye irritation - 0.7857 78.57%
Skin irritation - 0.8102 81.02%
Skin corrosion - 0.9609 96.09%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6382 63.82%
Micronuclear - 0.5067 50.67%
Hepatotoxicity - 0.7000 70.00%
skin sensitisation - 0.8743 87.43%
Respiratory toxicity - 0.6333 63.33%
Reproductive toxicity + 0.5889 58.89%
Mitochondrial toxicity - 0.6750 67.50%
Nephrotoxicity - 0.8102 81.02%
Acute Oral Toxicity (c) III 0.7844 78.44%
Estrogen receptor binding - 0.6148 61.48%
Androgen receptor binding - 0.7076 70.76%
Thyroid receptor binding - 0.5855 58.55%
Glucocorticoid receptor binding + 0.5789 57.89%
Aromatase binding - 0.6641 66.41%
PPAR gamma - 0.6897 68.97%
Honey bee toxicity - 0.9235 92.35%
Biodegradation - 0.5500 55.00%
Crustacea aquatic toxicity - 0.7015 70.15%
Fish aquatic toxicity - 0.5277 52.77%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.17% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.67% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 95.01% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.90% 86.33%
CHEMBL3194 P02766 Transthyretin 90.08% 90.71%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.28% 94.00%
CHEMBL4208 P20618 Proteasome component C5 87.41% 90.00%
CHEMBL2581 P07339 Cathepsin D 87.27% 98.95%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 86.36% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.18% 89.00%
CHEMBL2535 P11166 Glucose transporter 83.09% 98.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.02% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.57% 95.89%
CHEMBL3401 O75469 Pregnane X receptor 81.50% 94.73%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Capsicum annuum
Sargentodoxa cuneata

Cross-Links

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PubChem 14132344
LOTUS LTS0258367
wikiData Q27139670