(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one

Details

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Internal ID 2634c79d-bba3-431d-8eda-f8d9ced0c517
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
SMILES (Canonical) CC(=C)C1CCC2(C1C3CCC4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)C)C)C
SMILES (Isomeric) CC(=C)[C@@H]1CC[C@]2([C@@H]1[C@H]3CC[C@@H]4[C@]5(CCC(=O)C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)C)C
InChI InChI=1S/C30H48O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25-,27+,28-,29+,30+/m0/s1
InChI Key GRBHNQFQFHLCHO-MUZFUWECSA-N
Popularity 20 references in papers

Physical and Chemical Properties

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Molecular Formula C30H48O
Molecular Weight 424.70 g/mol
Exact Mass 424.370516150 g/mol
Topological Polar Surface Area (TPSA) 17.10 Ų
XlogP 9.60
Atomic LogP (AlogP) 8.23
H-Bond Acceptor 1
H-Bond Donor 0
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9972 99.72%
Caco-2 - 0.5206 52.06%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.4922 49.22%
OATP2B1 inhibitior - 0.7252 72.52%
OATP1B1 inhibitior + 0.8986 89.86%
OATP1B3 inhibitior - 0.3303 33.03%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior + 0.9081 90.81%
P-glycoprotein inhibitior - 0.6975 69.75%
P-glycoprotein substrate - 0.8018 80.18%
CYP3A4 substrate + 0.6411 64.11%
CYP2C9 substrate - 0.8039 80.39%
CYP2D6 substrate - 0.7758 77.58%
CYP3A4 inhibition - 0.8408 84.08%
CYP2C9 inhibition - 0.8670 86.70%
CYP2C19 inhibition - 0.5701 57.01%
CYP2D6 inhibition - 0.9589 95.89%
CYP1A2 inhibition - 0.8231 82.31%
CYP2C8 inhibition - 0.5713 57.13%
CYP inhibitory promiscuity - 0.7721 77.21%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.4936 49.36%
Eye corrosion - 0.9819 98.19%
Eye irritation - 0.8382 83.82%
Skin irritation + 0.6465 64.65%
Skin corrosion - 0.9735 97.35%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3838 38.38%
Micronuclear - 0.9600 96.00%
Hepatotoxicity - 0.8375 83.75%
skin sensitisation + 0.8396 83.96%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity + 0.5473 54.73%
Acute Oral Toxicity (c) III 0.6116 61.16%
Estrogen receptor binding + 0.8051 80.51%
Androgen receptor binding + 0.7665 76.65%
Thyroid receptor binding + 0.6415 64.15%
Glucocorticoid receptor binding + 0.8494 84.94%
Aromatase binding + 0.7173 71.73%
PPAR gamma + 0.6449 64.49%
Honey bee toxicity - 0.7337 73.37%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.9960 99.60%

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
CHEMBL241 Q14432 Phosphodiesterase 3A 93.11% 92.94%
CHEMBL1937 Q92769 Histone deacetylase 2 92.20% 94.75%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.95% 94.45%
CHEMBL2581 P07339 Cathepsin D 90.42% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.39% 97.25%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 89.14% 96.38%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.65% 82.69%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.84% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 84.68% 93.04%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 84.40% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 83.91% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.39% 97.09%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 83.34% 96.09%
CHEMBL259 P32245 Melanocortin receptor 4 82.95% 95.38%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.57% 95.56%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.54% 93.03%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 80.51% 97.50%

Plants that contains it

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Cross-Links

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PubChem 7092730
LOTUS LTS0012580
wikiData Q105015699