(1S,2R,6S,7R,9R,10R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,10-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

Details

• Internal ID: 323a5419-23c4-44c0-99a6-a166a5e71a33
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (1S,2R,6S,7R,9R,10R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,10-dihydroxy-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(CCC4C3C(C5C6(C4(C(=O)C=CC6O)C)O5)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@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)O)C)O)C
• InChI: InChI=1S/C28H38O7/c1-13-12-20(34-24(32)14(13)2)27(5,33)17-7-6-15-21-16(10-11-25(15,17)3)26(4)18(29)8-9-19(30)28(26)23(35-28)22(21)31/h8-9,15-17,19-23,30-31,33H,6-7,10-12H2,1-5H3/t15-,16-,17-,19-,20+,21-,22+,23+,25-,26-,27+,28+/m0/s1
• InChI Key: DMGHRMQAHYJTHX-YZYVTENCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₇
• Molecular Weight: 486.60 g/mol
• Exact Mass: 486.26175355 g/mol
• Topological Polar Surface Area (TPSA): 117.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 7
• 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	+	0.9485	94.85%
Caco-2	-	0.6995	69.95%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7352	73.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8776	87.76%
OATP1B3 inhibitior	+	0.9074	90.74%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6374	63.74%
BSEP inhibitior	+	0.7151	71.51%
P-glycoprotein inhibitior	-	0.4451	44.51%
P-glycoprotein substrate	-	0.5641	56.41%
CYP3A4 substrate	+	0.7387	73.87%
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	+	0.4778	47.78%
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	-	0.9584	95.84%
Skin irritation	+	0.5378	53.78%
Skin corrosion	-	0.9027	90.27%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3882	38.82%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8099	80.99%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6290	62.90%
Acute Oral Toxicity (c)	I	0.3175	31.75%
Estrogen receptor binding	+	0.7958	79.58%
Androgen receptor binding	+	0.7450	74.50%
Thyroid receptor binding	+	0.5395	53.95%
Glucocorticoid receptor binding	+	0.7472	74.72%
Aromatase binding	+	0.7996	79.96%
PPAR gamma	+	0.6023	60.23%
Honey bee toxicity	-	0.8307	83.07%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9852	98.52%

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	94.53%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.54%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.51%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.93%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.33%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.18%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.92%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.65%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.65%	93.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.57%	85.14%
CHEMBL1871	P10275	Androgen Receptor	86.39%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.19%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	86.08%	94.73%
CHEMBL1902	P62942	FK506-binding protein 1A	85.32%	97.05%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.61%	90.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.13%	93.04%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.77%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.38%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.26%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.13%	91.11%

Plants that contains it

• Eriolarynx australis

Cross-Links

• PubChem: 23266160
• NPASS: NPC293112