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(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[3-(4-hydroxyphenyl)prop-2-enoyloxy]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-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 1416d364-a1fa-417c-b067-fc1e2d4bedbc
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[3-(4-hydroxyphenyl)prop-2-enoyloxy]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
SMILES (Canonical) CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)C=CC6=CC=C(C=C6)O)C)C(=O)O
SMILES (Isomeric) CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)C=CC6=CC=C(C=C6)O)C)C(=O)O
InChI InChI=1S/C39H54O5/c1-24(2)27-16-21-39(34(42)43)23-22-37(6)28(33(27)39)13-14-30-36(5)19-18-31(35(3,4)29(36)17-20-38(30,37)7)44-32(41)15-10-25-8-11-26(40)12-9-25/h8-12,15,27-31,33,40H,1,13-14,16-23H2,2-7H3,(H,42,43)/t27-,28+,29-,30+,31-,33+,36-,37+,38+,39-/m0/s1
InChI Key QYUWZMVAARIGMO-PPBXDVGMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C39H54O5
Molecular Weight 602.80 g/mol
Exact Mass 602.39712482 g/mol
Topological Polar Surface Area (TPSA) 83.80 Ų
XlogP 10.50
Atomic LogP (AlogP) 9.06
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[3-(4-hydroxyphenyl)prop-2-enoyloxy]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-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 + 0.9934 99.34%
Caco-2 - 0.8243 82.43%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8830 88.30%
OATP2B1 inhibitior - 0.5673 56.73%
OATP1B1 inhibitior + 0.8231 82.31%
OATP1B3 inhibitior - 0.7401 74.01%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.7071 70.71%
BSEP inhibitior + 0.9277 92.77%
P-glycoprotein inhibitior + 0.7041 70.41%
P-glycoprotein substrate - 0.5342 53.42%
CYP3A4 substrate + 0.7125 71.25%
CYP2C9 substrate - 0.8038 80.38%
CYP2D6 substrate - 0.8877 88.77%
CYP3A4 inhibition - 0.6762 67.62%
CYP2C9 inhibition - 0.7311 73.11%
CYP2C19 inhibition - 0.7178 71.78%
CYP2D6 inhibition - 0.9366 93.66%
CYP1A2 inhibition + 0.5302 53.02%
CYP2C8 inhibition + 0.8681 86.81%
CYP inhibitory promiscuity - 0.7681 76.81%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.6296 62.96%
Eye corrosion - 0.9949 99.49%
Eye irritation - 0.9298 92.98%
Skin irritation - 0.5265 52.65%
Skin corrosion - 0.9543 95.43%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7807 78.07%
Micronuclear - 0.7100 71.00%
Hepatotoxicity - 0.7823 78.23%
skin sensitisation - 0.6976 69.76%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.8073 80.73%
Acute Oral Toxicity (c) III 0.5299 52.99%
Estrogen receptor binding + 0.7463 74.63%
Androgen receptor binding + 0.8099 80.99%
Thyroid receptor binding + 0.5388 53.88%
Glucocorticoid receptor binding + 0.7536 75.36%
Aromatase binding + 0.7086 70.86%
PPAR gamma + 0.7326 73.26%
Honey bee toxicity - 0.6952 69.52%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5300 53.00%
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
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.27% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.03% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.80% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.28% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.53% 96.09%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 91.16% 96.09%
CHEMBL206 P03372 Estrogen receptor alpha 89.46% 97.64%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.01% 97.09%
CHEMBL2581 P07339 Cathepsin D 88.95% 98.95%
CHEMBL340 P08684 Cytochrome P450 3A4 87.22% 91.19%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.74% 95.89%
CHEMBL241 Q14432 Phosphodiesterase 3A 86.19% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.37% 89.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 85.01% 100.00%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 84.41% 94.97%
CHEMBL4040 P28482 MAP kinase ERK2 84.40% 83.82%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.78% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.98% 100.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 80.82% 97.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.50% 99.17%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 80.21% 100.00%

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.
Strychnos vanprukii

Cross-Links

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PubChem 162995617
LOTUS LTS0241991
wikiData Q105230713