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[(3S,4R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-hydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-4-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

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 4edfb3c6-e5f8-43df-9101-bd799009ddd5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name [(3S,4R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-hydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-4-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
SMILES (Canonical) CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)COC(=O)C=CC6=CC(=C(C=C6)O)O)O)C)C)C2C1)C)CO)C
SMILES (Isomeric) C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)CO)C)C)(C)COC(=O)/C=C/C6=CC(=C(C=C6)O)O)O
InChI InChI=1S/C39H56O6/c1-34(2)17-19-39(23-40)20-18-37(5)26(27(39)22-34)9-11-31-35(3)15-14-32(43)36(4,30(35)13-16-38(31,37)6)24-45-33(44)12-8-25-7-10-28(41)29(42)21-25/h7-10,12,21,27,30-32,40-43H,11,13-20,22-24H2,1-6H3/b12-8+/t27-,30+,31+,32-,35-,36-,37+,38+,39+/m0/s1
InChI Key DYOQDMIWQJGRQY-YIEOTUJOSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C39H56O6
Molecular Weight 620.90 g/mol
Exact Mass 620.40768950 g/mol
Topological Polar Surface Area (TPSA) 107.00 Ų
XlogP 8.30
Atomic LogP (AlogP) 7.79
H-Bond Acceptor 6
H-Bond Donor 4
Rotatable Bonds 5

Synonyms

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23-(3,4-Dihydroxycinnamoyloxy)oleana-12-ene-3beta,28-diol
3-(3,4-Dihydroxyphenyl)propenoic acid 3beta,28-dihydroxyoleana-12-ene-23-yl ester

2D Structure

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2D Structure of [(3S,4R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-hydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-4-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9895 98.95%
Caco-2 - 0.8098 80.98%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.9048 90.48%
OATP2B1 inhibitior - 0.5704 57.04%
OATP1B1 inhibitior + 0.8841 88.41%
OATP1B3 inhibitior - 0.3500 35.00%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.7526 75.26%
BSEP inhibitior + 0.9836 98.36%
P-glycoprotein inhibitior + 0.7317 73.17%
P-glycoprotein substrate - 0.5951 59.51%
CYP3A4 substrate + 0.7148 71.48%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8681 86.81%
CYP3A4 inhibition - 0.8160 81.60%
CYP2C9 inhibition - 0.7143 71.43%
CYP2C19 inhibition - 0.6647 66.47%
CYP2D6 inhibition - 0.9107 91.07%
CYP1A2 inhibition + 0.6031 60.31%
CYP2C8 inhibition + 0.7904 79.04%
CYP inhibitory promiscuity - 0.9090 90.90%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.6589 65.89%
Eye corrosion - 0.9934 99.34%
Eye irritation - 0.9285 92.85%
Skin irritation - 0.7028 70.28%
Skin corrosion - 0.9588 95.88%
Ames mutagenesis - 0.7770 77.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7777 77.77%
Micronuclear - 0.8200 82.00%
Hepatotoxicity - 0.8000 80.00%
skin sensitisation - 0.8402 84.02%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.8769 87.69%
Acute Oral Toxicity (c) III 0.6341 63.41%
Estrogen receptor binding + 0.7851 78.51%
Androgen receptor binding + 0.8023 80.23%
Thyroid receptor binding + 0.5513 55.13%
Glucocorticoid receptor binding + 0.8033 80.33%
Aromatase binding + 0.7299 72.99%
PPAR gamma + 0.7227 72.27%
Honey bee toxicity - 0.7745 77.45%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9973 99.73%

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 98.95% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.55% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.48% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.08% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.00% 86.33%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 92.27% 95.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.84% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.55% 89.00%
CHEMBL221 P23219 Cyclooxygenase-1 90.24% 90.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.06% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.35% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.55% 91.07%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.35% 99.15%
CHEMBL1951 P21397 Monoamine oxidase A 84.72% 91.49%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 84.24% 91.03%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 82.90% 91.71%
CHEMBL3194 P02766 Transthyretin 82.18% 90.71%
CHEMBL2581 P07339 Cathepsin D 81.99% 98.95%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 80.25% 96.95%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.24% 97.21%

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.
Hibiscus syriacus

Cross-Links

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PubChem 10603919
NPASS NPC271494
LOTUS LTS0231589
wikiData Q104991485