Withaferin A

Details

• Internal ID: dbb4affd-4a0a-4bdc-be16-14ce37bf8b0a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-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)CO
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[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)CO
• InChI: InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
• InChI Key: DBRXOUCRJQVYJQ-CKNDUULBSA-N
• Popularity: 1,292 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₆
• Molecular Weight: 470.60 g/mol
• Exact Mass: 470.26683893 g/mol
• Topological Polar Surface Area (TPSA): 96.40 Ų
• XlogP: 3.80

Synonyms

• 5119-48-2
• Withaferine A
• NSC 273757
• WITHAFERIN DERIV JPR, IOWA U. COMPOUND
• CHEBI:69120
• NSC-101088
• NSC101088
• L6DO3QW4K5
• CHEMBL517080
• Ashwagandha
• NSC-273757
• 4beta,27-dihydroxy-1-oxo-5beta,6beta-epoxywitha-2,24-dienolide
• (1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
• (6S,7R,9R)-6-Hydroxy-15-[(2R,3R)-3-hydroxy-4-(4-methyl-5-oxo-2H-furan-3-yl)butan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
• UNII-L6DO3QW4K5
• BRN 1335150
• 5.beta.-Ergosta-2, 5,6.beta.-epoxy-4.beta.,22,27-trihydroxy-1-oxo-, .delta.-lactone, (20S,22R)-
• Ergosta-2, 5,6-epoxy-4,22,27-trihydroxy-1-oxo-, .delta.-lactone, (4.beta.,5.beta.,6.beta.,22R)-
• NSC 101088
• WITHAFERIN A [MI]
• 5-19-06-00604 (Beilstein Handbook Reference)
• MLS006010687
• SCHEMBL157208
• Withaferin A, analytical standard
• Withaferin A, >=95% (HPLC)
• HY-N2065
• BDBM50599323
• MFCD10687098
• NSC273757
• s8587
• AKOS040758787
• (4beta,5beta,6beta,22R)-4,27-dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
• NCGC00180796-02
• (4beta,5beta,6beta,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid, delta-lactone
• 5-beta-Ergosta-2,24-dien-26-oic acid, 5,6-beta-epoxy-4-beta,22,27-trihydroxy-1-oxo-, delta-lactone, (20S,22R)-
• 5beta-Ergosta-2,24-dien-26-oic acid, 5,6beta-epoxy-4beta,22,27-trihydroxy-1-oxo-, delta-lactone, (20S,22R)-
• AS-77575
• Ergosta-2,24-dien-26-oic acid, 5,6-epoxy-4,22,27-trihydroxy-1-oxo-, gamma-lactone, (4bta,5beta,6beta,22R)-
• NCI60_000031
• SMR004701668
• CS-0018562
• Withaferin A 100 microg/mL in Acetonitrile
• C08841
• A871350
• A1-06845
• Q6606395
• BRD-K88378636-001-01-0
• WLN: T3 F5 E666 1A R AXO OV PU CH&TTTTJ J1 N1 RQ IY1&- FT6OV CUTJ C1Q D1
• (4.BETA.,5.BETA.,6.BETA.,22R)-4,27-DIHYDROXY-5,6:22,26-DIEPOXYERGOSTA-2,24-DIENE-1,26-DIONE
• (4S,4aR,5aR,6aS,6bS,9R,9aS,11aS,11bR)-4-hydroxy-9-((S)-1-((R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-one
• Ergosta-2,24-dien-26-oicacid, 5,6-epoxy-4,22,27-trihydroxy-1-oxo-, d-lactone, (4b,5b,6b,22R)-
• NCGC00180796-02_C28H38O6_(4beta,5beta,6beta,22R)-4,27-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	316.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.38%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.26%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.70%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.11%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.05%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.35%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	86.95%	97.79%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.27%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.97%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.34%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.87%	82.69%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.53%	90.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.90%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.67%	93.04%
CHEMBL1871	P10275	Androgen Receptor	81.52%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.91%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.44%	93.56%
CHEMBL5028	O14672	ADAM10	80.35%	97.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.23%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.11%	95.89%

Plants that contains it

• Physalis longifolia
• Vassobia breviflora
• Withania aristata
• Withania coagulans
• Withania somnifera

Cross-Links

• PubChem: 265237
• LOTUS: LTS0081840
• wikiData: Q6606395