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Withanolide

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 c4fb57c6-8640-43a7-9a13-2a25db432d44
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1S,2R,6S,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-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)(C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)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]3C[C@@H]5C6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)O)C
InChI InChI=1S/C28H38O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,21-23,30,32H,6-7,10-13H2,1-5H3/t16-,17-,18-,19-,21-,22+,23+,25-,26-,27+,28?/m0/s1
InChI Key SASUFNRGCZMRFD-LYOLWDNZSA-N
Popularity 29 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O6
Molecular Weight 470.60 g/mol
Exact Mass 470.26683893 g/mol
Topological Polar Surface Area (TPSA) 96.40 Ų
XlogP 3.10
Atomic LogP (AlogP) 3.50
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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(1S,2R,6S,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one
LMST01160018
5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oate
5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid
(4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oate
(4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid
(4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid delta-lactone

2D Structure

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2D Structure of Withanolide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9485 94.85%
Caco-2 - 0.6274 62.74%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.7352 73.52%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8630 86.30%
OATP1B3 inhibitior + 0.9074 90.74%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6374 63.74%
BSEP inhibitior + 0.7655 76.55%
P-glycoprotein inhibitior - 0.4303 43.03%
P-glycoprotein substrate - 0.5144 51.44%
CYP3A4 substrate + 0.7523 75.23%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8956 89.56%
CYP3A4 inhibition - 0.8598 85.98%
CYP2C9 inhibition - 0.8654 86.54%
CYP2C19 inhibition - 0.8991 89.91%
CYP2D6 inhibition - 0.9546 95.46%
CYP1A2 inhibition - 0.6315 63.15%
CYP2C8 inhibition + 0.5056 50.56%
CYP inhibitory promiscuity - 0.9632 96.32%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5701 57.01%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9602 96.02%
Skin irritation + 0.5378 53.78%
Skin corrosion - 0.9027 90.27%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6831 68.31%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.6033 60.33%
skin sensitisation - 0.8099 80.99%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.6522 65.22%
Acute Oral Toxicity (c) I 0.3175 31.75%
Estrogen receptor binding + 0.8055 80.55%
Androgen receptor binding + 0.7810 78.10%
Thyroid receptor binding + 0.5605 56.05%
Glucocorticoid receptor binding + 0.7817 78.17%
Aromatase binding + 0.7790 77.90%
PPAR gamma + 0.6592 65.92%
Honey bee toxicity - 0.7946 79.46%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6400 64.00%
Fish aquatic toxicity + 0.9852 98.52%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.04% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.49% 95.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 90.53% 97.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.80% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.39% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.96% 99.23%
CHEMBL1871 P10275 Androgen Receptor 87.61% 96.43%
CHEMBL1902 P62942 FK506-binding protein 1A 85.86% 97.05%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.35% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 83.08% 82.69%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.72% 93.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.40% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.28% 95.89%
CHEMBL2581 P07339 Cathepsin D 82.14% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 82.02% 94.73%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.53% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.32% 93.04%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 80.66% 97.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.28% 89.00%

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.
Solanum torvum

Cross-Links

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PubChem 53477765
NPASS NPC158307