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(2R)-2-[(1R)-1-[(1S,3R,8S,9S,10R,13S,14S,17S)-1,3-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-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 83c84d33-b0ea-4d17-b900-3584d0efbd33
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1R)-1-[(1S,3R,8S,9S,10R,13S,14S,17S)-1,3-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC=C5C4(C(CC(C5)O)O)C)C)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4([C@H](C[C@@H](C5)O)O)C)C)O)C
InChI InChI=1S/C28H42O5/c1-15-12-24(33-25(31)16(15)2)28(5,32)22-9-8-20-19-7-6-17-13-18(29)14-23(30)27(17,4)21(19)10-11-26(20,22)3/h6,18-24,29-30,32H,7-14H2,1-5H3/t18-,19+,20+,21+,22+,23+,24-,26+,27+,28-/m1/s1
InChI Key YATGOOKAKMOJRD-VSMZHVHMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H42O5
Molecular Weight 458.60 g/mol
Exact Mass 458.30322444 g/mol
Topological Polar Surface Area (TPSA) 87.00 Ų
XlogP 4.00
Atomic LogP (AlogP) 4.30
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(1R)-1-[(1S,3R,8S,9S,10R,13S,14S,17S)-1,3-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-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 + 0.9643 96.43%
Caco-2 - 0.6029 60.29%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.6915 69.15%
OATP2B1 inhibitior - 0.5739 57.39%
OATP1B1 inhibitior + 0.8962 89.62%
OATP1B3 inhibitior + 0.9077 90.77%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.6071 60.71%
BSEP inhibitior + 0.8424 84.24%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate + 0.5121 51.21%
CYP3A4 substrate + 0.7664 76.64%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8859 88.59%
CYP3A4 inhibition - 0.8432 84.32%
CYP2C9 inhibition - 0.9354 93.54%
CYP2C19 inhibition - 0.9118 91.18%
CYP2D6 inhibition - 0.9490 94.90%
CYP1A2 inhibition - 0.7869 78.69%
CYP2C8 inhibition + 0.5309 53.09%
CYP inhibitory promiscuity - 0.9469 94.69%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5733 57.33%
Eye corrosion - 0.9927 99.27%
Eye irritation - 0.9512 95.12%
Skin irritation + 0.6886 68.86%
Skin corrosion - 0.9186 91.86%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7046 70.46%
Micronuclear - 0.8300 83.00%
Hepatotoxicity + 0.6000 60.00%
skin sensitisation - 0.8375 83.75%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.5577 55.77%
Acute Oral Toxicity (c) I 0.4074 40.74%
Estrogen receptor binding + 0.8205 82.05%
Androgen receptor binding + 0.7934 79.34%
Thyroid receptor binding + 0.5615 56.15%
Glucocorticoid receptor binding + 0.8028 80.28%
Aromatase binding + 0.7190 71.90%
PPAR gamma + 0.6374 63.74%
Honey bee toxicity - 0.8295 82.95%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.6600 66.00%
Fish aquatic toxicity + 0.9678 96.78%

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 92.36% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.30% 100.00%
CHEMBL1871 P10275 Androgen Receptor 92.19% 96.43%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.35% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.10% 97.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.00% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.19% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.63% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.80% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 86.52% 94.73%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.44% 95.89%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 84.90% 97.33%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.71% 93.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.58% 99.23%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.24% 93.04%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.20% 97.14%
CHEMBL5028 O14672 ADAM10 81.80% 97.50%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 80.94% 96.95%
CHEMBL2581 P07339 Cathepsin D 80.74% 98.95%
CHEMBL1937 Q92769 Histone deacetylase 2 80.61% 94.75%
CHEMBL5103 Q969S8 Histone deacetylase 10 80.34% 90.08%

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.
Eriolarynx australis
Withania somnifera

Cross-Links

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PubChem 13743207
LOTUS LTS0147241
wikiData Q105345572