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[(1S,2R,6S,7S,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-15-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-6-yl] acetate

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 82ed641e-0c2f-499a-a1b4-b673b623d6d0
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name [(1S,2R,6S,7S,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-15-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-6-yl] acetate
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2(CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6OC(=O)C)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]6OC(=O)C)C)O5)C)O)O)C
InChI InChI=1S/C30H40O8/c1-15-13-23(37-25(33)16(15)2)28(6,34)29(35)12-10-19-18-14-24-30(38-24)22(36-17(3)31)8-7-21(32)27(30,5)20(18)9-11-26(19,29)4/h7-8,18-20,22-24,34-35H,9-14H2,1-6H3/t18-,19-,20-,22-,23-,24+,26-,27-,28-,29+,30+/m0/s1
InChI Key AGZAGLYJUCJXRY-GMWMVLEPSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C30H40O8
Molecular Weight 528.60 g/mol
Exact Mass 528.27231823 g/mol
Topological Polar Surface Area (TPSA) 123.00 Ų
XlogP 2.30
Atomic LogP (AlogP) 3.18
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2R,6S,7S,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2S)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-15-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-6-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9211 92.11%
Caco-2 - 0.7582 75.82%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7167 71.67%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8635 86.35%
OATP1B3 inhibitior + 0.8837 88.37%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6624 66.24%
BSEP inhibitior + 0.8650 86.50%
P-glycoprotein inhibitior + 0.7171 71.71%
P-glycoprotein substrate + 0.5673 56.73%
CYP3A4 substrate + 0.7441 74.41%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9001 90.01%
CYP3A4 inhibition - 0.7352 73.52%
CYP2C9 inhibition - 0.7951 79.51%
CYP2C19 inhibition - 0.8351 83.51%
CYP2D6 inhibition - 0.9478 94.78%
CYP1A2 inhibition - 0.7370 73.70%
CYP2C8 inhibition + 0.6758 67.58%
CYP inhibitory promiscuity - 0.9741 97.41%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5989 59.89%
Eye corrosion - 0.9905 99.05%
Eye irritation - 0.9281 92.81%
Skin irritation + 0.5191 51.91%
Skin corrosion - 0.9135 91.35%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6862 68.62%
Micronuclear - 0.6500 65.00%
Hepatotoxicity + 0.5283 52.83%
skin sensitisation - 0.8389 83.89%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity + 0.8035 80.35%
Acute Oral Toxicity (c) I 0.3768 37.68%
Estrogen receptor binding + 0.8117 81.17%
Androgen receptor binding + 0.7988 79.88%
Thyroid receptor binding + 0.5537 55.37%
Glucocorticoid receptor binding + 0.7369 73.69%
Aromatase binding + 0.7922 79.22%
PPAR gamma + 0.6813 68.13%
Honey bee toxicity - 0.7423 74.23%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9828 98.28%

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 96.80% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.77% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.93% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.61% 91.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 92.47% 97.14%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 92.05% 93.04%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.03% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.87% 96.09%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.66% 82.69%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.07% 91.07%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.87% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.70% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.17% 100.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 85.51% 93.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.20% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.00% 94.00%
CHEMBL340 P08684 Cytochrome P450 3A4 84.64% 91.19%
CHEMBL5028 O14672 ADAM10 84.32% 97.50%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 83.43% 94.08%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.49% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.64% 95.89%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.20% 97.33%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.16% 97.28%

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 162972520
LOTUS LTS0270629
wikiData Q104912114