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20-Hydroxycholesterol

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 c8d400ac-fef0-49bd-978a-09d1b5c09bad
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Cholestane steroids > Cholesterols and derivatives
IUPAC Name (3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-6-methylheptan-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(C)CCCC(C)(C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
SMILES (Isomeric) CC(C)CCC[C@@](C)([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O
InChI InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1
InChI Key MCKLJFJEQRYRQT-APGJSSKUSA-N
Popularity 148 references in papers

Physical and Chemical Properties

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Molecular Formula C27H46O2
Molecular Weight 402.70 g/mol
Exact Mass 402.349780706 g/mol
Topological Polar Surface Area (TPSA) 40.50 Ų
XlogP 6.90
Atomic LogP (AlogP) 6.50
H-Bond Acceptor 2
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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20(S)-hydroxycholesterol
20alpha-Hydroxycholesterol
516-72-3
(20S)-20-Hydroxycholesterol
20alpha-hydroxy cholesterol
cholest-5-en-3beta,20-diol
CHEBI:1296
(3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
30060WAL99
(3alpha,8alpha)-Cholest-5-Ene-3,20-Diol
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of 20-Hydroxycholesterol

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 + 0.5114 51.14%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.5918 59.18%
OATP2B1 inhibitior - 0.5906 59.06%
OATP1B1 inhibitior + 0.9486 94.86%
OATP1B3 inhibitior + 0.9717 97.17%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.7794 77.94%
P-glycoprotein inhibitior - 0.6358 63.58%
P-glycoprotein substrate + 0.7976 79.76%
CYP3A4 substrate + 0.7283 72.83%
CYP2C9 substrate - 0.5811 58.11%
CYP2D6 substrate - 0.7340 73.40%
CYP3A4 inhibition - 0.8517 85.17%
CYP2C9 inhibition - 0.9270 92.70%
CYP2C19 inhibition - 0.8107 81.07%
CYP2D6 inhibition - 0.9429 94.29%
CYP1A2 inhibition - 0.8907 89.07%
CYP2C8 inhibition + 0.4742 47.42%
CYP inhibitory promiscuity - 0.5193 51.93%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.5928 59.28%
Eye corrosion - 0.9929 99.29%
Eye irritation - 0.9576 95.76%
Skin irritation + 0.5398 53.98%
Skin corrosion - 0.9598 95.98%
Ames mutagenesis - 0.8500 85.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7132 71.32%
Micronuclear - 0.9500 95.00%
Hepatotoxicity + 0.5467 54.67%
skin sensitisation + 0.5137 51.37%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity - 0.9198 91.98%
Acute Oral Toxicity (c) III 0.6859 68.59%
Estrogen receptor binding + 0.8594 85.94%
Androgen receptor binding + 0.7624 76.24%
Thyroid receptor binding + 0.6473 64.73%
Glucocorticoid receptor binding + 0.8213 82.13%
Aromatase binding + 0.5642 56.42%
PPAR gamma + 0.5508 55.08%
Honey bee toxicity - 0.8531 85.31%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6400 64.00%
Fish aquatic toxicity + 0.9869 98.69%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1741186 P51449 Nuclear receptor ROR-gamma 20 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 97.10% 96.09%
CHEMBL226 P30542 Adenosine A1 receptor 96.97% 95.93%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.53% 97.25%
CHEMBL2581 P07339 Cathepsin D 95.59% 98.95%
CHEMBL2996 Q05655 Protein kinase C delta 94.60% 97.79%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.21% 91.11%
CHEMBL3359 P21462 Formyl peptide receptor 1 92.72% 93.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.13% 97.09%
CHEMBL2179 P04062 Beta-glucocerebrosidase 92.04% 85.31%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.46% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 91.04% 95.89%
CHEMBL237 P41145 Kappa opioid receptor 90.33% 98.10%
CHEMBL4227 P25090 Lipoxin A4 receptor 88.94% 100.00%
CHEMBL242 Q92731 Estrogen receptor beta 88.45% 98.35%
CHEMBL1871 P10275 Androgen Receptor 88.37% 96.43%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.69% 94.45%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 85.95% 90.71%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.88% 95.89%
CHEMBL4581 P52732 Kinesin-like protein 1 85.03% 93.18%
CHEMBL3892 Q99500 Sphingosine 1-phosphate receptor Edg-3 85.01% 97.29%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 84.71% 89.05%
CHEMBL2959 Q08881 Tyrosine-protein kinase ITK/TSK 83.83% 95.00%
CHEMBL1937 Q92769 Histone deacetylase 2 81.88% 94.75%
CHEMBL1907 P15144 Aminopeptidase N 81.47% 93.31%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.74% 82.69%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 80.08% 91.03%

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 121935
LOTUS LTS0017372
wikiData Q27067423