2-[1-hydroxy-1-(5,6,14,17-tetrahydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl)ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one

Details

• Internal ID: d968c9cd-3c3d-4b29-a543-2d70639265f9
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: 2-[1-hydroxy-1-(5,6,14,17-tetrahydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl)ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)C)O)O)O)C
• SMILES (Isomeric): CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)C)O)O)O)C
• InChI: InChI=1S/C28H40O8/c1-15-13-21(36-22(31)16(15)2)25(5,32)28(35)12-11-26(33)18-14-20(30)27(34)9-6-7-19(29)24(27,4)17(18)8-10-23(26,28)3/h6-7,17-18,20-21,30,32-35H,8-14H2,1-5H3
• InChI Key: PQZVBIJEPVKNOZ-UHFFFAOYSA-N
• Popularity: 805 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₈
• Molecular Weight: 504.60 g/mol
• Exact Mass: 504.27231823 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• 63139-16-2
• NSC312620
• 2-[1-hydroxy-1-(5,6,14,17-tetrahydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-yl)ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
• DTXSID00317201
• NSC-312620
• WITHAFERIN DERIV B665685K000
• Ergosta-2, 5,6,14,17,20,22-hexahydroxy-1-oxo-, .delta.-lactone, (5.alpha.,6.beta.,17.alpha.,22R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8825	88.25%
Caco-2	-	0.6936	69.36%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6991	69.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8968	89.68%
OATP1B3 inhibitior	+	0.9071	90.71%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6124	61.24%
BSEP inhibitior	+	0.7791	77.91%
P-glycoprotein inhibitior	-	0.4930	49.30%
P-glycoprotein substrate	+	0.5640	56.40%
CYP3A4 substrate	+	0.7062	70.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9070	90.70%
CYP3A4 inhibition	-	0.8227	82.27%
CYP2C9 inhibition	-	0.9250	92.50%
CYP2C19 inhibition	-	0.8933	89.33%
CYP2D6 inhibition	-	0.9567	95.67%
CYP1A2 inhibition	-	0.8472	84.72%
CYP2C8 inhibition	+	0.5278	52.78%
CYP inhibitory promiscuity	-	0.9806	98.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6250	62.50%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9367	93.67%
Skin irritation	+	0.6575	65.75%
Skin corrosion	-	0.9074	90.74%
Ames mutagenesis	-	0.6590	65.90%
Human Ether-a-go-go-Related Gene inhibition	+	0.7373	73.73%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6660	66.60%
skin sensitisation	-	0.8347	83.47%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6762	67.62%
Acute Oral Toxicity (c)	I	0.5312	53.12%
Estrogen receptor binding	+	0.7968	79.68%
Androgen receptor binding	+	0.7789	77.89%
Thyroid receptor binding	+	0.6247	62.47%
Glucocorticoid receptor binding	+	0.6979	69.79%
Aromatase binding	+	0.7667	76.67%
PPAR gamma	+	0.6166	61.66%
Honey bee toxicity	-	0.8404	84.04%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9773	97.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.75%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.84%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.34%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.90%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.72%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.91%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.57%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.46%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.68%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.14%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.61%	86.33%
CHEMBL1871	P10275	Androgen Receptor	85.27%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.85%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.77%	93.56%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.83%	90.93%
CHEMBL2996	Q05655	Protein kinase C delta	80.70%	97.79%

Plants that contains it

• Physalis cinerascens
• Physalis peruviana
• Withania somnifera

Cross-Links

• PubChem: 329485
• LOTUS: LTS0008576
• wikiData: Q82071676