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(2R)-5-(hydroxymethyl)-4-methyl-2-[(1S)-1-[(8S,9S,10S,13S,14S,17R)-9,10,13-trimethyl-3-oxo-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethyl]-2,3-dihydropyran-6-one

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 9a3cfdfd-5f77-4f03-aeb8-5a5280476855
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-5-(hydroxymethyl)-4-methyl-2-[(1S)-1-[(8S,9S,10S,13S,14S,17R)-9,10,13-trimethyl-3-oxo-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethyl]-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4(C3CCC5=CC(=O)C=CC54C)C)C)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@]4([C@H]3CCC5=CC(=O)C=C[C@@]54C)C)C)CO
InChI InChI=1S/C29H40O4/c1-17-14-25(33-26(32)21(17)16-30)18(2)22-8-9-23-24-7-6-19-15-20(31)10-11-28(19,4)29(24,5)13-12-27(22,23)3/h10-11,15,18,22-25,30H,6-9,12-14,16H2,1-5H3/t18-,22+,23-,24-,25+,27+,28-,29-/m0/s1
InChI Key CYFAPZFVQGEVID-SFLKSZFZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H40O4
Molecular Weight 452.60 g/mol
Exact Mass 452.29265975 g/mol
Topological Polar Surface Area (TPSA) 63.60 Ų
XlogP 6.30
Atomic LogP (AlogP) 5.56
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-5-(hydroxymethyl)-4-methyl-2-[(1S)-1-[(8S,9S,10S,13S,14S,17R)-9,10,13-trimethyl-3-oxo-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethyl]-2,3-dihydropyran-6-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9659 96.59%
Caco-2 + 0.5068 50.68%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.7950 79.50%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8083 80.83%
OATP1B3 inhibitior + 0.9546 95.46%
MATE1 inhibitior - 0.9212 92.12%
OCT2 inhibitior + 0.5412 54.12%
BSEP inhibitior + 0.9776 97.76%
P-glycoprotein inhibitior + 0.7456 74.56%
P-glycoprotein substrate + 0.5127 51.27%
CYP3A4 substrate + 0.7084 70.84%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9109 91.09%
CYP3A4 inhibition - 0.6580 65.80%
CYP2C9 inhibition - 0.9351 93.51%
CYP2C19 inhibition - 0.9531 95.31%
CYP2D6 inhibition - 0.9577 95.77%
CYP1A2 inhibition - 0.6190 61.90%
CYP2C8 inhibition + 0.5929 59.29%
CYP inhibitory promiscuity - 0.9128 91.28%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6143 61.43%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9658 96.58%
Skin irritation + 0.6583 65.83%
Skin corrosion - 0.9375 93.75%
Ames mutagenesis - 0.5914 59.14%
Human Ether-a-go-go-Related Gene inhibition + 0.7369 73.69%
Micronuclear - 0.8100 81.00%
Hepatotoxicity - 0.5926 59.26%
skin sensitisation - 0.9053 90.53%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity - 0.7817 78.17%
Acute Oral Toxicity (c) III 0.7411 74.11%
Estrogen receptor binding + 0.8173 81.73%
Androgen receptor binding + 0.8223 82.23%
Thyroid receptor binding + 0.6900 69.00%
Glucocorticoid receptor binding + 0.9089 90.89%
Aromatase binding + 0.7562 75.62%
PPAR gamma + 0.6697 66.97%
Honey bee toxicity - 0.8240 82.40%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9781 97.81%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.68% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.88% 97.25%
CHEMBL2581 P07339 Cathepsin D 94.33% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.45% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.04% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.53% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.29% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.55% 99.23%
CHEMBL226 P30542 Adenosine A1 receptor 88.94% 95.93%
CHEMBL3192 Q9BY41 Histone deacetylase 8 87.44% 93.99%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.94% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.36% 95.89%
CHEMBL1937 Q92769 Histone deacetylase 2 85.88% 94.75%
CHEMBL1871 P10275 Androgen Receptor 85.46% 96.43%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.20% 86.33%
CHEMBL5103 Q969S8 Histone deacetylase 10 83.94% 90.08%
CHEMBL2996 Q05655 Protein kinase C delta 82.39% 97.79%
CHEMBL5028 O14672 ADAM10 82.31% 97.50%
CHEMBL4072 P07858 Cathepsin B 82.19% 93.67%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.64% 89.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.87% 95.89%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.50% 93.04%
CHEMBL3310 Q96DB2 Histone deacetylase 11 80.44% 88.56%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.22% 82.69%

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.
Withania somnifera

Cross-Links

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PubChem 162873961
LOTUS LTS0058548
wikiData Q104972271