(2R,3S,5S,8R,9R,10R,13S,14R,17S)-17-[(E,2S,3R,4R)-3,4-dihydroxy-5-propan-2-ylhept-5-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-2,3-diol

Details

• Internal ID: 77aa25d3-e04d-4853-879b-7fb1c35374e1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Stigmastanes and derivatives
• IUPAC Name: (2R,3S,5S,8R,9R,10R,13S,14R,17S)-17-[(E,2S,3R,4R)-3,4-dihydroxy-5-propan-2-ylhept-5-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-2,3-diol
• SMILES (Canonical): CC=C(C(C)C)C(C(C(C)C1CCC2C1(CCC3C2CCC4C3(CC(C(C4)O)O)C)C)O)O
• SMILES (Isomeric): C/C=C(/[C@H]([C@@H]([C@@H](C)[C@@H]1CC[C@H]2[C@@]1(CC[C@@H]3[C@H]2CC[C@@H]4[C@]3(C[C@H]([C@H](C4)O)O)C)C)O)O)\C(C)C
• InChI: InChI=1S/C29H50O4/c1-7-19(16(2)3)27(33)26(32)17(4)21-10-11-22-20-9-8-18-14-24(30)25(31)15-29(18,6)23(20)12-13-28(21,22)5/h7,16-18,20-27,30-33H,8-15H2,1-6H3/b19-7+/t17-,18-,20-,21-,22+,23+,24-,25+,26+,27+,28+,29+/m0/s1
• InChI Key: GQSRIBUSVVSLSQ-STPBSKNSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₅₀O₄
• Molecular Weight: 462.70 g/mol
• Exact Mass: 462.37091007 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 4.94
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	-	0.7329	73.29%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6860	68.60%
OATP2B1 inhibitior	-	0.5785	57.85%
OATP1B1 inhibitior	+	0.8147	81.47%
OATP1B3 inhibitior	+	0.9141	91.41%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	-	0.6176	61.76%
P-glycoprotein inhibitior	-	0.5573	55.73%
P-glycoprotein substrate	-	0.5824	58.24%
CYP3A4 substrate	+	0.7021	70.21%
CYP2C9 substrate	-	0.6284	62.84%
CYP2D6 substrate	-	0.7127	71.27%
CYP3A4 inhibition	-	0.8457	84.57%
CYP2C9 inhibition	-	0.8811	88.11%
CYP2C19 inhibition	-	0.8402	84.02%
CYP2D6 inhibition	-	0.9502	95.02%
CYP1A2 inhibition	-	0.8802	88.02%
CYP2C8 inhibition	-	0.7246	72.46%
CYP inhibitory promiscuity	-	0.8962	89.62%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6460	64.60%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9429	94.29%
Skin irritation	+	0.6137	61.37%
Skin corrosion	-	0.9431	94.31%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4282	42.82%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5320	53.20%
skin sensitisation	-	0.6061	60.61%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8880	88.80%
Acute Oral Toxicity (c)	III	0.5079	50.79%
Estrogen receptor binding	+	0.7185	71.85%
Androgen receptor binding	+	0.7323	73.23%
Thyroid receptor binding	+	0.6469	64.69%
Glucocorticoid receptor binding	+	0.6521	65.21%
Aromatase binding	+	0.5783	57.83%
PPAR gamma	+	0.5944	59.44%
Honey bee toxicity	-	0.6490	64.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9895	98.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.82%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.75%	91.11%
CHEMBL284	P27487	Dipeptidyl peptidase IV	95.56%	95.69%
CHEMBL221	P23219	Cyclooxygenase-1	94.02%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.48%	97.25%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.31%	96.38%
CHEMBL2094135	Q96BI3	Gamma-secretase	92.02%	98.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.01%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.92%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	89.59%	95.93%
CHEMBL237	P41145	Kappa opioid receptor	88.97%	98.10%
CHEMBL2179	P04062	Beta-glucocerebrosidase	88.50%	85.31%
CHEMBL1914	P06276	Butyrylcholinesterase	87.43%	95.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.82%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.39%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.60%	89.05%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.49%	95.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.76%	82.69%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.38%	85.30%
CHEMBL1871	P10275	Androgen Receptor	83.35%	96.43%
CHEMBL4302	P08183	P-glycoprotein 1	82.95%	92.98%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.93%	95.58%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.81%	95.50%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	81.49%	92.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.48%	92.62%
CHEMBL240	Q12809	HERG	81.31%	89.76%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	80.80%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.60%	92.86%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.34%	98.75%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	80.21%	99.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.05%	95.36%

Plants that contains it

• Phaseolus vulgaris

Cross-Links

• PubChem: 163004275
• LOTUS: LTS0204246
• wikiData: Q105015558