4-ethyl-6-[1-hydroxy-1-[(2S,3R,5R,10R,13R,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]-3-methyloxan-2-one

Details

• Internal ID: ba0a0449-733c-4344-a927-940bace28a4d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: 4-ethyl-6-[1-hydroxy-1-[(2S,3R,5R,10R,13R,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]-3-methyloxan-2-one
• SMILES (Canonical): CCC1CC(OC(=O)C1C)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O
• SMILES (Isomeric): CCC1CC(OC(=O)C1C)C(C)([C@H]2CCC3([C@@]2(CCC4C3=CC(=O)[C@H]5[C@@]4(C[C@@H]([C@@H](C5)O)O)C)C)O)O
• InChI: InChI=1S/C29H44O7/c1-6-16-11-24(36-25(33)15(16)2)28(5,34)23-8-10-29(35)18-12-20(30)19-13-21(31)22(32)14-26(19,3)17(18)7-9-27(23,29)4/h12,15-17,19,21-24,31-32,34-35H,6-11,13-14H2,1-5H3/t15?,16?,17?,19-,21+,22-,23-,24?,26+,27+,28?,29?/m0/s1
• InChI Key: GGAHWMQNGYKGTF-OIFRWYPSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₇
• Molecular Weight: 504.70 g/mol
• Exact Mass: 504.30870374 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9716	97.16%
Caco-2	-	0.5351	53.51%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7833	78.33%
OATP2B1 inhibitior	-	0.5692	56.92%
OATP1B1 inhibitior	+	0.8680	86.80%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8763	87.63%
P-glycoprotein inhibitior	-	0.5141	51.41%
P-glycoprotein substrate	+	0.5842	58.42%
CYP3A4 substrate	+	0.6917	69.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9048	90.48%
CYP3A4 inhibition	+	0.5863	58.63%
CYP2C9 inhibition	-	0.8915	89.15%
CYP2C19 inhibition	-	0.8298	82.98%
CYP2D6 inhibition	-	0.9310	93.10%
CYP1A2 inhibition	-	0.8854	88.54%
CYP2C8 inhibition	-	0.6063	60.63%
CYP inhibitory promiscuity	-	0.9356	93.56%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6349	63.49%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.9417	94.17%
Skin irritation	+	0.7061	70.61%
Skin corrosion	-	0.9218	92.18%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4656	46.56%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5555	55.55%
skin sensitisation	-	0.8437	84.37%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8455	84.55%
Acute Oral Toxicity (c)	IV	0.3609	36.09%
Estrogen receptor binding	+	0.7502	75.02%
Androgen receptor binding	+	0.7601	76.01%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7551	75.51%
Aromatase binding	+	0.6921	69.21%
PPAR gamma	+	0.5461	54.61%
Honey bee toxicity	-	0.8328	83.28%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9910	99.10%

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	99.70%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.31%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.21%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.12%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.25%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.82%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.03%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.76%	100.00%
CHEMBL2581	P07339	Cathepsin D	89.47%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.60%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.08%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.67%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.99%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.83%	86.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.81%	97.14%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	83.74%	94.78%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.11%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.77%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.74%	95.71%
CHEMBL1871	P10275	Androgen Receptor	82.23%	96.43%
CHEMBL1902	P62942	FK506-binding protein 1A	82.07%	97.05%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.06%	91.07%
CHEMBL4660	P28907	Lymphocyte differentiation antigen CD38	81.71%	95.27%

Plants that contains it

• Artemisia capillaris

Cross-Links

• PubChem: 5315676
• NPASS: NPC158243