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(4aS,6aR,6bR,10S,12aR,14bS)-6a-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-10-[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]oxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

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 1016ec42-1ca6-410b-8a97-01c312b83ca6
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (4aS,6aR,6bR,10S,12aR,14bS)-6a-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-10-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
SMILES (Canonical) CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC(=O)C=CC6=CC(=C(C=C6)O)OC)C)C)C2C1)COC(=O)C=CC7=CC(=C(C=C7)O)O)C(=O)O)C
SMILES (Isomeric) C[C@]12CC[C@@H](C(C1CC[C@@]3(C2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)COC(=O)/C=C/C6=CC(=C(C=C6)O)O)C)(C)C)OC(=O)/C=C/C7=CC(=C(C=C7)O)OC
InChI InChI=1S/C49H62O10/c1-44(2)22-23-48(43(55)56)24-25-49(29-58-41(53)16-10-30-8-13-34(50)36(52)26-30)32(33(48)28-44)12-15-39-46(5)20-19-40(45(3,4)38(46)18-21-47(39,49)6)59-42(54)17-11-31-9-14-35(51)37(27-31)57-7/h8-14,16-17,26-27,33,38-40,50-52H,15,18-25,28-29H2,1-7H3,(H,55,56)/b16-10+,17-11+/t33-,38?,39?,40-,46-,47+,48-,49-/m0/s1
InChI Key OKBFTHVVTZUXNK-UBCWEOEXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C49H62O10
Molecular Weight 811.00 g/mol
Exact Mass 810.43429817 g/mol
Topological Polar Surface Area (TPSA) 160.00 Ų
XlogP 10.30
Atomic LogP (AlogP) 9.86
H-Bond Acceptor 9
H-Bond Donor 4
Rotatable Bonds 9

Synonyms

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Olean-12-en-28-oic acid, 27-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3-[[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]oxy]-, (3.beta.,5.xi.,9.xi.)-

2D Structure

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2D Structure of (4aS,6aR,6bR,10S,12aR,14bS)-6a-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-10-[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]oxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9831 98.31%
Caco-2 - 0.8407 84.07%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.9212 92.12%
OATP2B1 inhibitior - 0.8617 86.17%
OATP1B1 inhibitior + 0.7562 75.62%
OATP1B3 inhibitior - 0.2474 24.74%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior + 0.9925 99.25%
P-glycoprotein inhibitior + 0.7874 78.74%
P-glycoprotein substrate + 0.5245 52.45%
CYP3A4 substrate + 0.7130 71.30%
CYP2C9 substrate - 0.8028 80.28%
CYP2D6 substrate - 0.8704 87.04%
CYP3A4 inhibition - 0.6687 66.87%
CYP2C9 inhibition - 0.6104 61.04%
CYP2C19 inhibition - 0.6369 63.69%
CYP2D6 inhibition - 0.9102 91.02%
CYP1A2 inhibition + 0.7068 70.68%
CYP2C8 inhibition + 0.8467 84.67%
CYP inhibitory promiscuity - 0.8347 83.47%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9020 90.20%
Carcinogenicity (trinary) Non-required 0.6939 69.39%
Eye corrosion - 0.9931 99.31%
Eye irritation - 0.9100 91.00%
Skin irritation - 0.7443 74.43%
Skin corrosion - 0.9588 95.88%
Ames mutagenesis - 0.7900 79.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6854 68.54%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.6834 68.34%
skin sensitisation - 0.8643 86.43%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity - 0.9555 95.55%
Acute Oral Toxicity (c) III 0.5345 53.45%
Estrogen receptor binding + 0.8132 81.32%
Androgen receptor binding + 0.7880 78.80%
Thyroid receptor binding + 0.5855 58.55%
Glucocorticoid receptor binding + 0.7622 76.22%
Aromatase binding + 0.6468 64.68%
PPAR gamma + 0.7852 78.52%
Honey bee toxicity - 0.7200 72.00%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5045 50.45%
Fish aquatic toxicity + 1.0000 100.00%

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 99.57% 91.11%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 99.12% 95.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.56% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.21% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.28% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.71% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.37% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 88.96% 90.17%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 88.79% 89.62%
CHEMBL3194 P02766 Transthyretin 88.01% 90.71%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.42% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.85% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.17% 89.00%
CHEMBL5028 O14672 ADAM10 82.78% 97.50%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 82.45% 99.15%
CHEMBL340 P08684 Cytochrome P450 3A4 81.40% 91.19%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.00% 99.17%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 80.96% 91.03%
CHEMBL2179 P04062 Beta-glucocerebrosidase 80.44% 85.31%

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 taiwanensis
Myrica cerifera

Cross-Links

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PubChem 5274625
LOTUS LTS0013182
wikiData Q105193446