(2R)-4-[(1R)-1-hydroxyethyl]-2-[(1R)-1-hydroxy-1-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-methyl-2,3-dihydropyran-6-one

Details

• Internal ID: cb4eb3fc-a001-41fd-9a21-96eee645b5f7
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (2R)-4-[(1R)-1-hydroxyethyl]-2-[(1R)-1-hydroxy-1-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-methyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(CC(OC1=O)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C(C)O
• SMILES (Isomeric): CC1=C(C[C@@H](OC1=O)[C@@](C)([C@H]2CC[C@@]3([C@@]2(CC[C@H]4C3=CC(=O)[C@H]5[C@@]4(C[C@@H]([C@@H](C5)O)O)C)C)O)O)[C@@H](C)O
• InChI: InChI=1S/C29H42O8/c1-14-16(15(2)30)10-24(37-25(14)34)28(5,35)23-7-9-29(36)18-11-20(31)19-12-21(32)22(33)13-26(19,3)17(18)6-8-27(23,29)4/h11,15,17,19,21-24,30,32-33,35-36H,6-10,12-13H2,1-5H3/t15-,17+,19+,21-,22+,23+,24-,26-,27-,28-,29-/m1/s1
• InChI Key: MMGMZHFGVCRNFJ-WIYWGDAXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂O₈
• Molecular Weight: 518.60 g/mol
• Exact Mass: 518.28796829 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.95
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9576	95.76%
Caco-2	-	0.6388	63.88%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8163	81.63%
OATP2B1 inhibitior	-	0.7159	71.59%
OATP1B1 inhibitior	+	0.8881	88.81%
OATP1B3 inhibitior	+	0.9132	91.32%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5624	56.24%
BSEP inhibitior	+	0.7720	77.20%
P-glycoprotein inhibitior	-	0.4533	45.33%
P-glycoprotein substrate	+	0.5970	59.70%
CYP3A4 substrate	+	0.7101	71.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9048	90.48%
CYP3A4 inhibition	-	0.8025	80.25%
CYP2C9 inhibition	-	0.9162	91.62%
CYP2C19 inhibition	-	0.9089	90.89%
CYP2D6 inhibition	-	0.9449	94.49%
CYP1A2 inhibition	-	0.8189	81.89%
CYP2C8 inhibition	-	0.5980	59.80%
CYP inhibitory promiscuity	-	0.9793	97.93%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6081	60.81%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9367	93.67%
Skin irritation	+	0.6855	68.55%
Skin corrosion	-	0.9129	91.29%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4013	40.13%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	-	0.8152	81.52%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8375	83.75%
Acute Oral Toxicity (c)	IV	0.4455	44.55%
Estrogen receptor binding	+	0.7704	77.04%
Androgen receptor binding	+	0.7299	72.99%
Thyroid receptor binding	+	0.5746	57.46%
Glucocorticoid receptor binding	+	0.7700	77.00%
Aromatase binding	+	0.7172	71.72%
PPAR gamma	+	0.6144	61.44%
Honey bee toxicity	-	0.8131	81.31%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9855	98.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.72%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.23%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.63%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.45%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.17%	97.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.34%	82.69%
CHEMBL2581	P07339	Cathepsin D	91.00%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.81%	97.09%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	90.10%	94.78%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.83%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.69%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.94%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.27%	96.61%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.17%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.44%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.66%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.00%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.91%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.40%	100.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.82%	85.94%
CHEMBL1902	P62942	FK506-binding protein 1A	80.49%	97.05%

Plants that contains it

• Ajuga iva
• Ajuga reptans

Cross-Links

• PubChem: 152754669
• LOTUS: LTS0076242
• wikiData: Q105167735