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[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 3,4-dimethoxybenzoate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 9f1b400b-322c-42c8-80b6-c9a77cd49a95
Taxonomy Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
IUPAC Name [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 3,4-dimethoxybenzoate
SMILES (Canonical) CC1(CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C4=CC(=C(C=C4)OC)OC)O
SMILES (Isomeric) C[C@@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)C4=CC(=C(C=C4)OC)OC)O
InChI InChI=1S/C24H32O12/c1-24(30)9-15(34-21(29)11-4-5-13(31-2)14(8-11)32-3)12-6-7-33-22(17(12)24)36-23-20(28)19(27)18(26)16(10-25)35-23/h4-8,12,15-20,22-23,25-28,30H,9-10H2,1-3H3/t12-,15+,16+,17+,18+,19-,20+,22-,23-,24-/m0/s1
InChI Key SBWYWSYCORCAIO-FTUCCGIQSA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C24H32O12
Molecular Weight 512.50 g/mol
Exact Mass 512.18937645 g/mol
Topological Polar Surface Area (TPSA) 174.00 Ų
XlogP 0.00
Atomic LogP (AlogP) -0.70
H-Bond Acceptor 12
H-Bond Donor 5
Rotatable Bonds 7

Synonyms

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3,4-Dimethoxybenzoic acid (1S)-1alpha-(beta-D-glucopyranosyloxy)-7alpha-hydroxy-7-methyl-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta[c]pyran-5alpha-yl ester

2D Structure

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2D Structure of [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 3,4-dimethoxybenzoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7612 76.12%
Caco-2 - 0.8425 84.25%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.4897 48.97%
OATP2B1 inhibitior - 0.8641 86.41%
OATP1B1 inhibitior + 0.8556 85.56%
OATP1B3 inhibitior + 0.9403 94.03%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.5265 52.65%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate - 0.5428 54.28%
CYP3A4 substrate + 0.6872 68.72%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8503 85.03%
CYP3A4 inhibition - 0.8502 85.02%
CYP2C9 inhibition - 0.9319 93.19%
CYP2C19 inhibition - 0.9028 90.28%
CYP2D6 inhibition - 0.8829 88.29%
CYP1A2 inhibition - 0.7952 79.52%
CYP2C8 inhibition + 0.6766 67.66%
CYP inhibitory promiscuity - 0.8488 84.88%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5829 58.29%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9477 94.77%
Skin irritation - 0.7680 76.80%
Skin corrosion - 0.9429 94.29%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6618 66.18%
Micronuclear - 0.5426 54.26%
Hepatotoxicity - 0.7348 73.48%
skin sensitisation - 0.8492 84.92%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.7678 76.78%
Acute Oral Toxicity (c) III 0.5229 52.29%
Estrogen receptor binding + 0.7813 78.13%
Androgen receptor binding - 0.5596 55.96%
Thyroid receptor binding + 0.5518 55.18%
Glucocorticoid receptor binding + 0.6468 64.68%
Aromatase binding + 0.5330 53.30%
PPAR gamma + 0.7124 71.24%
Honey bee toxicity - 0.7966 79.66%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.7015 70.15%
Fish aquatic toxicity + 0.8178 81.78%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.09% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.16% 91.11%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 95.78% 96.21%
CHEMBL241 Q14432 Phosphodiesterase 3A 95.32% 92.94%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.89% 86.33%
CHEMBL4208 P20618 Proteasome component C5 92.38% 90.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.62% 99.17%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 90.18% 96.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.38% 95.89%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 88.33% 96.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.39% 94.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 87.09% 95.83%
CHEMBL220 P22303 Acetylcholinesterase 86.00% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.59% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.59% 97.09%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 82.43% 97.21%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.08% 91.07%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.70% 97.14%
CHEMBL2535 P11166 Glucose transporter 81.67% 98.75%
CHEMBL2581 P07339 Cathepsin D 81.09% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.70% 100.00%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 80.22% 86.92%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.20% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.18% 95.56%

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.
Handroanthus impetiginosus

Cross-Links

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PubChem 23900071
NPASS NPC249007
LOTUS LTS0246581
wikiData Q105249757