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(3S,8S,9S,10R,13R,14S,17R)-17-((R)-4-((R)-3,3-Dimethyloxiran-2-yl)butan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

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 f10879cf-8717-4a7d-ab28-b327c431881a
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Cholestane steroids > Cholesterols and derivatives
IUPAC Name (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2R)-3,3-dimethyloxiran-2-yl]butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
SMILES (Canonical) CC(CCC1C(O1)(C)C)C2CCC3C2(CCC4C3CC=C5C4(CCC(C5)O)C)C
SMILES (Isomeric) C[C@H](CC[C@@H]1C(O1)(C)C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O)C)C
InChI InChI=1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24-,26+,27-/m1/s1
InChI Key OSENKJZWYQXHBN-PJXSLZQESA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C27H44O2
Molecular Weight 400.60 g/mol
Exact Mass 400.334130642 g/mol
Topological Polar Surface Area (TPSA) 32.80 Ų
XlogP 6.60
Atomic LogP (AlogP) 6.52
H-Bond Acceptor 2
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2R)-3,3-dimethyloxiran-2-yl]butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,8S,9S,10R,13R,14S,17R)-17-((R)-4-((R)-3,3-Dimethyloxiran-2-yl)butan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
24(R),25-epoxycholesterol
CHEMBL171744
SCHEMBL1917975
SCHEMBL29828485
BDBM20174
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-4-[(2R)-3,3-dimethyloxiran-2-yl]butan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-7-en-5-ol

2D Structure

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2D Structure of (3S,8S,9S,10R,13R,14S,17R)-17-((R)-4-((R)-3,3-Dimethyloxiran-2-yl)butan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 1.0000 100.00%
Caco-2 + 0.5311 53.11%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.5286 52.86%
Subcellular localzation Mitochondria 0.5230 52.30%
OATP2B1 inhibitior - 0.5927 59.27%
OATP1B1 inhibitior + 0.9332 93.32%
OATP1B3 inhibitior + 0.9656 96.56%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.7927 79.27%
P-glycoprotein inhibitior - 0.5480 54.80%
P-glycoprotein substrate + 0.8036 80.36%
CYP3A4 substrate + 0.7317 73.17%
CYP2C9 substrate - 0.6206 62.06%
CYP2D6 substrate - 0.7163 71.63%
CYP3A4 inhibition - 0.7518 75.18%
CYP2C9 inhibition - 0.7989 79.89%
CYP2C19 inhibition - 0.7401 74.01%
CYP2D6 inhibition - 0.9350 93.50%
CYP1A2 inhibition - 0.7767 77.67%
CYP2C8 inhibition + 0.4903 49.03%
CYP inhibitory promiscuity - 0.6993 69.93%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5837 58.37%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9657 96.57%
Skin irritation - 0.5705 57.05%
Skin corrosion - 0.9422 94.22%
Ames mutagenesis - 0.8500 85.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3983 39.83%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.5435 54.35%
skin sensitisation + 0.5000 50.00%
Respiratory toxicity + 0.8889 88.89%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.8023 80.23%
Acute Oral Toxicity (c) III 0.5263 52.63%
Estrogen receptor binding + 0.8348 83.48%
Androgen receptor binding + 0.8085 80.85%
Thyroid receptor binding + 0.6500 65.00%
Glucocorticoid receptor binding + 0.8236 82.36%
Aromatase binding + 0.5722 57.22%
PPAR gamma - 0.5000 50.00%
Honey bee toxicity - 0.7652 76.52%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9668 96.68%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL2808 Q13133 LXR-alpha 95 nM
 EC50
 via Super-PRED
CHEMBL4093 P55055 LXR-beta 168 nM
 EC50
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.06% 96.09%
CHEMBL226 P30542 Adenosine A1 receptor 96.00% 95.93%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.08% 91.11%
CHEMBL2581 P07339 Cathepsin D 92.15% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.12% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 91.00% 95.89%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.44% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.25% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.41% 97.25%
CHEMBL3359 P21462 Formyl peptide receptor 1 88.71% 93.56%
CHEMBL237 P41145 Kappa opioid receptor 87.01% 98.10%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 86.25% 90.71%
CHEMBL221 P23219 Cyclooxygenase-1 86.00% 90.17%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 84.45% 89.05%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.18% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.15% 89.00%
CHEMBL1871 P10275 Androgen Receptor 82.65% 96.43%
CHEMBL2140 P48775 Tryptophan 2,3-dioxygenase 82.32% 98.46%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.91% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.83% 93.04%
CHEMBL2094135 Q96BI3 Gamma-secretase 80.46% 98.05%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 15597289
LOTUS LTS0105834
wikiData Q105198834