methyl 3-[(3aR,5aR,6S,7S,9aR,9bR)-9a,9b-dimethyl-7-prop-1-en-2-yl-3a,4,5,5a,6,7,8,9-octahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate

Details

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Internal ID eb8734d7-d2da-410b-8223-72696e9b9a74
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
IUPAC Name methyl 3-[(3aR,5aR,6S,7S,9aR,9bR)-9a,9b-dimethyl-7-prop-1-en-2-yl-3a,4,5,5a,6,7,8,9-octahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate
SMILES (Canonical) CC(=C)C1CCC2(C(C1CCC(=O)OC)CCC3C2(CC=C3)C)C
SMILES (Isomeric) CC(=C)[C@H]1CC[C@@]2([C@@H]([C@H]1CCC(=O)OC)CC[C@H]3[C@]2(CC=C3)C)C
InChI InChI=1S/C22H34O2/c1-15(2)17-12-14-22(4)19(18(17)9-11-20(23)24-5)10-8-16-7-6-13-21(16,22)3/h6-7,16-19H,1,8-14H2,2-5H3/t16-,17+,18-,19+,21+,22+/m0/s1
InChI Key GZLOULXNCLGCGH-MYBSLXOZSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H34O2
Molecular Weight 330.50 g/mol
Exact Mass 330.255880323 g/mol
Topological Polar Surface Area (TPSA) 26.30 Ų
XlogP 6.40
Atomic LogP (AlogP) 5.54
H-Bond Acceptor 2
H-Bond Donor 0
Rotatable Bonds 4

Synonyms

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methyl 3-[(3aR,5aR,6S,7S,9aR,9bR)-9a,9b-dimethyl-7-prop-1-en-2-yl-3a,4,5,5a,6,7,8,9-octahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate
Mansumbinoic acid
DTXSID70908089
1H-Benz(e)indene-6-propanoic acid, 3a,4,5,5a,6,7,8,9,9a,9b-decahydro-6,9a,9b-trimethyl-7-(1-methylethenyl)-, (3aR-(3aalpha,5abeta,6beta,7alpha,9aalpha,9bbeta))-
Methyl 3-[9a,9b-dimethyl-7-(prop-1-en-2-yl)-3a,4,5,5a,6,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate

2D Structure

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2D Structure of methyl 3-[(3aR,5aR,6S,7S,9aR,9bR)-9a,9b-dimethyl-7-prop-1-en-2-yl-3a,4,5,5a,6,7,8,9-octahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9963 99.63%
Caco-2 + 0.8062 80.62%
Blood Brain Barrier + 0.9500 95.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Plasma membrane 0.4033 40.33%
OATP2B1 inhibitior - 0.8667 86.67%
OATP1B1 inhibitior + 0.8291 82.91%
OATP1B3 inhibitior - 0.3554 35.54%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.8350 83.50%
P-glycoprotein inhibitior - 0.5303 53.03%
P-glycoprotein substrate - 0.6296 62.96%
CYP3A4 substrate + 0.6541 65.41%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8683 86.83%
CYP3A4 inhibition - 0.7484 74.84%
CYP2C9 inhibition - 0.7930 79.30%
CYP2C19 inhibition - 0.5255 52.55%
CYP2D6 inhibition - 0.9460 94.60%
CYP1A2 inhibition - 0.8194 81.94%
CYP2C8 inhibition + 0.5265 52.65%
CYP inhibitory promiscuity - 0.6449 64.49%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8420 84.20%
Carcinogenicity (trinary) Non-required 0.5671 56.71%
Eye corrosion - 0.9780 97.80%
Eye irritation - 0.9276 92.76%
Skin irritation - 0.6429 64.29%
Skin corrosion - 0.9867 98.67%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8606 86.06%
Micronuclear - 0.8200 82.00%
Hepatotoxicity - 0.5241 52.41%
skin sensitisation + 0.4739 47.39%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.5778 57.78%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity - 0.5570 55.70%
Acute Oral Toxicity (c) III 0.8639 86.39%
Estrogen receptor binding + 0.7053 70.53%
Androgen receptor binding + 0.7208 72.08%
Thyroid receptor binding + 0.7018 70.18%
Glucocorticoid receptor binding + 0.7937 79.37%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.5245 52.45%
Honey bee toxicity - 0.7892 78.92%
Biodegradation - 0.7500 75.00%
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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.53% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.24% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.75% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.94% 85.14%
CHEMBL233 P35372 Mu opioid receptor 89.85% 97.93%
CHEMBL218 P21554 Cannabinoid CB1 receptor 89.45% 96.61%
CHEMBL4227 P25090 Lipoxin A4 receptor 88.82% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.96% 94.45%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 86.14% 94.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.04% 92.62%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.82% 91.07%
CHEMBL340 P08684 Cytochrome P450 3A4 84.65% 91.19%
CHEMBL2243 O00519 Anandamide amidohydrolase 83.96% 97.53%
CHEMBL221 P23219 Cyclooxygenase-1 83.77% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.93% 97.09%
CHEMBL2581 P07339 Cathepsin D 81.02% 98.95%
CHEMBL1871 P10275 Androgen Receptor 80.28% 96.43%

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.
Commiphora kua

Cross-Links

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PubChem 128211
LOTUS LTS0182030
wikiData Q82877476