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

Details

• Internal ID: 5ac2853d-9060-4ece-8f2a-da2c0e6a20fa
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Stigmastanes and derivatives
• IUPAC Name: (2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-[(E,2S,3R,4R)-3,4-dihydroxy-5-propan-2-ylhept-5-en-2-yl]-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC=C(C(C)C)C(C(C(C)C1CCC2C1(CCC3C2CC(=O)C4C3(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(=O)[C@@H]4[C@@]3(C[C@H]([C@H](C4)O)O)C)C)O)O)\C(C)C
• InChI: InChI=1S/C29H48O5/c1-7-17(15(2)3)27(34)26(33)16(4)19-8-9-20-18-12-23(30)22-13-24(31)25(32)14-29(22,6)21(18)10-11-28(19,20)5/h7,15-16,18-22,24-27,31-34H,8-14H2,1-6H3/b17-7+/t16-,18-,19+,20-,21-,22+,24-,25+,26+,27+,28+,29+/m0/s1
• InChI Key: DXUFRIYNOOTWEO-HPPPSGJZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₈O₅
• Molecular Weight: 476.70 g/mol
• Exact Mass: 476.35017463 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.12
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 85797-14-4
• DTXSID001316115

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	-	0.7019	70.19%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8076	80.76%
OATP2B1 inhibitior	-	0.7142	71.42%
OATP1B1 inhibitior	+	0.8095	80.95%
OATP1B3 inhibitior	+	0.9044	90.44%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5321	53.21%
BSEP inhibitior	+	0.5510	55.10%
P-glycoprotein inhibitior	-	0.5878	58.78%
P-glycoprotein substrate	-	0.5490	54.90%
CYP3A4 substrate	+	0.7034	70.34%
CYP2C9 substrate	-	0.8348	83.48%
CYP2D6 substrate	-	0.7829	78.29%
CYP3A4 inhibition	-	0.8240	82.40%
CYP2C9 inhibition	-	0.8615	86.15%
CYP2C19 inhibition	-	0.8493	84.93%
CYP2D6 inhibition	-	0.9519	95.19%
CYP1A2 inhibition	-	0.8836	88.36%
CYP2C8 inhibition	-	0.7571	75.71%
CYP inhibitory promiscuity	-	0.9252	92.52%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6334	63.34%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9560	95.60%
Skin irritation	+	0.6644	66.44%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.7770	77.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5576	55.76%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.5193	51.93%
skin sensitisation	-	0.6059	60.59%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7801	78.01%
Acute Oral Toxicity (c)	III	0.5526	55.26%
Estrogen receptor binding	+	0.7292	72.92%
Androgen receptor binding	+	0.7392	73.92%
Thyroid receptor binding	+	0.6024	60.24%
Glucocorticoid receptor binding	+	0.6366	63.66%
Aromatase binding	+	0.6046	60.46%
PPAR gamma	-	0.5197	51.97%
Honey bee toxicity	-	0.6634	66.34%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9923	99.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.42%	96.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	94.54%	85.31%
CHEMBL2581	P07339	Cathepsin D	93.11%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.69%	97.09%
CHEMBL1914	P06276	Butyrylcholinesterase	92.65%	95.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.13%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.71%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.04%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.94%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	88.74%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.60%	85.14%
CHEMBL284	P27487	Dipeptidyl peptidase IV	87.55%	95.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.80%	95.56%
CHEMBL1902	P62942	FK506-binding protein 1A	86.43%	97.05%
CHEMBL221	P23219	Cyclooxygenase-1	85.83%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.45%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.13%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.07%	92.62%
CHEMBL325	Q13547	Histone deacetylase 1	83.73%	95.92%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.64%	93.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.27%	95.89%
CHEMBL2094135	Q96BI3	Gamma-secretase	82.99%	98.05%
CHEMBL1871	P10275	Androgen Receptor	82.68%	96.43%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.55%	85.30%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.41%	89.00%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	81.99%	92.95%
CHEMBL237	P41145	Kappa opioid receptor	81.42%	98.10%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.18%	97.36%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.90%	93.04%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.60%	82.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.49%	96.77%

Plants that contains it

• Codiaeum variegatum
• Croton cajucara
• Digitalis isabelliana
• Garcinia lancilimba
• Madhuca longifolia
• Pilocarpus goudotianus
• Pinus elliottii
• Rhizophora mucronata
• Samanea saman

Cross-Links

• PubChem: 14607933
• NPASS: NPC231293