(2R)-2-[(1R)-1-[(4S,7R,8S,9S,10R,13S,14S,17S)-4,7-dihydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one

Details

• Internal ID: 8fa17e32-417a-44f9-b82d-087973508c6d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (2R)-2-[(1R)-1-[(4S,7R,8S,9S,10R,13S,14S,17S)-4,7-dihydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3C(C=C5C4(C(=O)C=CC5O)C)O)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]3[C@H](C=C5[C@@]4(C(=O)C=C[C@@H]5O)C)O)C)O)C
• InChI: InChI=1S/C28H38O6/c1-14-12-23(34-25(32)15(14)2)28(5,33)21-8-6-16-24-17(10-11-26(16,21)3)27(4)18(13-20(24)30)19(29)7-9-22(27)31/h7,9,13,16-17,19-21,23-24,29-30,33H,6,8,10-12H2,1-5H3/t16-,17-,19-,20-,21-,23+,24-,26-,27+,28+/m0/s1
• InChI Key: HMVXQIAJBGENDJ-MHYIOVDWSA-N
• Popularity: 2 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): 104.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.26
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9716	97.16%
Caco-2	-	0.7121	71.21%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8237	82.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8766	87.66%
OATP1B3 inhibitior	+	0.8779	87.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5876	58.76%
BSEP inhibitior	+	0.6576	65.76%
P-glycoprotein inhibitior	-	0.4324	43.24%
P-glycoprotein substrate	-	0.5814	58.14%
CYP3A4 substrate	+	0.7452	74.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9113	91.13%
CYP3A4 inhibition	-	0.8284	82.84%
CYP2C9 inhibition	-	0.9334	93.34%
CYP2C19 inhibition	-	0.9441	94.41%
CYP2D6 inhibition	-	0.9459	94.59%
CYP1A2 inhibition	-	0.6482	64.82%
CYP2C8 inhibition	-	0.5661	56.61%
CYP inhibitory promiscuity	-	0.9475	94.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9938	99.38%
Eye irritation	-	0.9654	96.54%
Skin irritation	+	0.6715	67.15%
Skin corrosion	-	0.9148	91.48%
Ames mutagenesis	-	0.6407	64.07%
Human Ether-a-go-go-Related Gene inhibition	-	0.4550	45.50%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5493	54.93%
skin sensitisation	-	0.8032	80.32%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6291	62.91%
Acute Oral Toxicity (c)	IV	0.5053	50.53%
Estrogen receptor binding	+	0.8296	82.96%
Androgen receptor binding	+	0.7130	71.30%
Thyroid receptor binding	+	0.6033	60.33%
Glucocorticoid receptor binding	+	0.8205	82.05%
Aromatase binding	+	0.7478	74.78%
PPAR gamma	+	0.5716	57.16%
Honey bee toxicity	-	0.8538	85.38%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9891	98.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.94%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.05%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.64%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.35%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.12%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.11%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.65%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.23%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.98%	90.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.60%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.08%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.84%	93.04%
CHEMBL1871	P10275	Androgen Receptor	82.66%	96.43%
CHEMBL3401	O75469	Pregnane X receptor	82.64%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.28%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	80.52%	83.82%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.13%	92.94%

Plants that contains it

• Eriolarynx australis

Cross-Links

• PubChem: 21679020
• NPASS: NPC37116