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(1R,2R,6S,7R,9R,11R,12S,15R,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,15-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-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 8666e714-c6bb-4c48-8501-a48c36372524
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1R,2R,6S,7R,9R,11R,12S,15R,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,15-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2(CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)O)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@]2(CC[C@@H]3[C@@]2(CC[C@@H]4[C@@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)O)O)C
InChI InChI=1S/C28H38O7/c1-14-12-21(34-23(31)15(14)2)26(5,32)27(33)11-9-17-16-13-22-28(35-22)20(30)7-6-19(29)25(28,4)18(16)8-10-24(17,27)3/h6-7,16-18,20-22,30,32-33H,8-13H2,1-5H3/t16-,17+,18-,20+,21-,22-,24+,25+,26+,27-,28-/m1/s1
InChI Key JVEUOKCSZLCPOI-SJXVKXAUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O7
Molecular Weight 486.60 g/mol
Exact Mass 486.26175355 g/mol
Topological Polar Surface Area (TPSA) 117.00 Ų
XlogP 1.70
Atomic LogP (AlogP) 2.61
H-Bond Acceptor 7
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 (1R,2R,6S,7R,9R,11R,12S,15R,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,15-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9242 92.42%
Caco-2 - 0.6997 69.97%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.6918 69.18%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8635 86.35%
OATP1B3 inhibitior + 0.9140 91.40%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6374 63.74%
BSEP inhibitior + 0.7220 72.20%
P-glycoprotein inhibitior - 0.4641 46.41%
P-glycoprotein substrate + 0.5382 53.82%
CYP3A4 substrate + 0.7276 72.76%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8924 89.24%
CYP3A4 inhibition - 0.7395 73.95%
CYP2C9 inhibition - 0.8398 83.98%
CYP2C19 inhibition - 0.8590 85.90%
CYP2D6 inhibition - 0.9534 95.34%
CYP1A2 inhibition - 0.7647 76.47%
CYP2C8 inhibition + 0.5623 56.23%
CYP inhibitory promiscuity - 0.9846 98.46%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5631 56.31%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9457 94.57%
Skin irritation + 0.5589 55.89%
Skin corrosion - 0.9047 90.47%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6557 65.57%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.6408 64.08%
skin sensitisation - 0.8202 82.02%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity + 0.7992 79.92%
Acute Oral Toxicity (c) I 0.4073 40.73%
Estrogen receptor binding + 0.8352 83.52%
Androgen receptor binding + 0.7978 79.78%
Thyroid receptor binding + 0.5964 59.64%
Glucocorticoid receptor binding + 0.7711 77.11%
Aromatase binding + 0.7980 79.80%
PPAR gamma + 0.6477 64.77%
Honey bee toxicity - 0.8006 80.06%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6200 62.00%
Fish aquatic toxicity + 0.9804 98.04%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.10% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.11% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.94% 85.14%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 92.24% 97.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.21% 91.11%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.48% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.05% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.96% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.37% 93.04%
CHEMBL1871 P10275 Androgen Receptor 84.51% 96.43%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 83.94% 82.69%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 83.55% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.40% 91.07%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.76% 93.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.26% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.91% 86.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.38% 94.00%
CHEMBL2581 P07339 Cathepsin D 81.25% 98.95%
CHEMBL5028 O14672 ADAM10 80.30% 97.50%
CHEMBL1902 P62942 FK506-binding protein 1A 80.07% 97.05%

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 162890388
LOTUS LTS0017682
wikiData Q105135645