(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R)-3,4-Dihydroxy-6-methyl-5-methylideneheptan-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: 5f7a7260-1f0f-4c45-93be-aab0b9c2169a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Tetrahydroxy bile acids, alcohols and derivatives
• IUPAC Name: (2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R)-3,4-dihydroxy-6-methyl-5-methylideneheptan-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)C1CCC2C1(CCC3C2CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O
• SMILES (Isomeric): C[C@@H]([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)[C@H]([C@@H](C(=C)C(C)C)O)O
• InChI: InChI=1S/C28H46O5/c1-14(2)15(3)25(32)26(33)16(4)18-7-8-19-17-11-22(29)21-12-23(30)24(31)13-28(21,6)20(17)9-10-27(18,19)5/h14,16-21,23-26,30-33H,3,7-13H2,1-2,4-6H3/t16-,17-,18+,19-,20-,21+,23-,24+,25+,26+,27+,28+/m0/s1
• InChI Key: CYPKCRFYMBXYBU-NJSRRFNUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₆O₅
• Molecular Weight: 462.70 g/mol
• Exact Mass: 462.33452456 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 3.73
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• (2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R)-3,4-Dihydroxy-6-methyl-5-methylideneheptan-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
• CHEBI:172693
• DTXSID301317362
• 85797-15-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	-	0.7052	70.52%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7782	77.82%
OATP2B1 inhibitior	-	0.5756	57.56%
OATP1B1 inhibitior	+	0.7715	77.15%
OATP1B3 inhibitior	-	0.2478	24.78%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5321	53.21%
BSEP inhibitior	-	0.5438	54.38%
P-glycoprotein inhibitior	-	0.6321	63.21%
P-glycoprotein substrate	-	0.5229	52.29%
CYP3A4 substrate	+	0.7170	71.70%
CYP2C9 substrate	-	0.8348	83.48%
CYP2D6 substrate	-	0.7829	78.29%
CYP3A4 inhibition	-	0.8025	80.25%
CYP2C9 inhibition	-	0.8541	85.41%
CYP2C19 inhibition	-	0.8288	82.88%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.8825	88.25%
CYP2C8 inhibition	-	0.7682	76.82%
CYP inhibitory promiscuity	-	0.9310	93.10%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6635	66.35%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9400	94.00%
Skin irritation	+	0.6469	64.69%
Skin corrosion	-	0.9415	94.15%
Ames mutagenesis	-	0.8170	81.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4140	41.40%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	+	0.5258	52.58%
skin sensitisation	-	0.6180	61.80%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7375	73.75%
Acute Oral Toxicity (c)	III	0.5854	58.54%
Estrogen receptor binding	+	0.6756	67.56%
Androgen receptor binding	+	0.7439	74.39%
Thyroid receptor binding	+	0.6099	60.99%
Glucocorticoid receptor binding	+	0.6266	62.66%
Aromatase binding	+	0.6023	60.23%
PPAR gamma	-	0.5590	55.90%
Honey bee toxicity	-	0.6527	65.27%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9962	99.62%

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	97.54%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.29%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.68%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.38%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.28%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.73%	100.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	90.29%	85.31%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.78%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.29%	96.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.55%	94.45%
CHEMBL1871	P10275	Androgen Receptor	85.78%	96.43%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.73%	90.71%
CHEMBL1902	P62942	FK506-binding protein 1A	85.44%	97.05%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.59%	93.04%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.88%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	83.47%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.20%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.04%	92.62%
CHEMBL299	P17252	Protein kinase C alpha	81.03%	98.03%

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: 10983436
• NPASS: NPC289809