(3S,5R,6S,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,4,6,7,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,5,6-triol

Details

• Internal ID: 820650d2-dae1-4e52-8a55-ac305f31a2bd
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cholestane steroids > Cholesterols and derivatives
• IUPAC Name: (3S,5R,6S,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,4,6,7,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,5,6-triol
• SMILES (Canonical): CC(CCC=C(C)C)C1CCC2C1(CCC3=C2CC(C4(C3(CCC(C4)O)C)O)O)C
• SMILES (Isomeric): C[C@H](CCC=C(C)C)[C@H]1CC[C@@H]2[C@@]1(CCC3=C2C[C@@H]([C@@]4([C@@]3(CC[C@@H](C4)O)C)O)O)C
• InChI: InChI=1S/C27H44O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h7,18-19,21-22,24,28-30H,6,8-16H2,1-5H3/t18-,19+,21-,22+,24+,25-,26-,27+/m1/s1
• InChI Key: NWTTZHBMXCCOSW-YACPQFPNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₃
• Molecular Weight: 416.60 g/mol
• Exact Mass: 416.32904526 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.54
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	+	0.5412	54.12%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6033	60.33%
OATP2B1 inhibitior	-	0.7268	72.68%
OATP1B1 inhibitior	+	0.8142	81.42%
OATP1B3 inhibitior	+	0.9517	95.17%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7964	79.64%
P-glycoprotein inhibitior	-	0.6600	66.00%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6461	64.61%
CYP2C9 substrate	-	0.5858	58.58%
CYP2D6 substrate	-	0.7545	75.45%
CYP3A4 inhibition	-	0.8976	89.76%
CYP2C9 inhibition	-	0.8306	83.06%
CYP2C19 inhibition	-	0.6924	69.24%
CYP2D6 inhibition	-	0.9442	94.42%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.7740	77.40%
CYP inhibitory promiscuity	-	0.7699	76.99%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6248	62.48%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9622	96.22%
Skin irritation	+	0.5410	54.10%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	-	0.7237	72.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3677	36.77%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5838	58.38%
skin sensitisation	-	0.7220	72.20%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6615	66.15%
Acute Oral Toxicity (c)	I	0.5741	57.41%
Estrogen receptor binding	+	0.8379	83.79%
Androgen receptor binding	+	0.8010	80.10%
Thyroid receptor binding	+	0.6976	69.76%
Glucocorticoid receptor binding	+	0.7978	79.78%
Aromatase binding	+	0.6895	68.95%
PPAR gamma	+	0.6213	62.13%
Honey bee toxicity	-	0.8045	80.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9845	98.45%

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	95.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.41%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.12%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.51%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	93.07%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.86%	97.25%
CHEMBL2581	P07339	Cathepsin D	90.72%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.24%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.64%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.28%	95.89%
CHEMBL1977	P11473	Vitamin D receptor	87.43%	99.43%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.33%	93.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.06%	95.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.82%	92.88%
CHEMBL1871	P10275	Androgen Receptor	83.73%	96.43%
CHEMBL1937	Q92769	Histone deacetylase 2	83.48%	94.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.98%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.19%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	81.58%	97.05%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.12%	96.38%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.96%	94.78%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.76%	97.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.47%	90.71%

Plants that contains it

• Achillea leptophylla
• Aldama cordifolia
• Cordiera macrophylla
• Dioscorea futschauensis
• Dorstenia barnimiana
• Petrosedum forsterianum
• Rubia yunnanensis
• Uvaria mocoli
• Verbascum georgicum
• Zieria chevalieri

Cross-Links

• PubChem: 11582441
• NPASS: NPC199756
• LOTUS: LTS0249710
• wikiData: Q105186810