(2S)-2-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-ene-1,2-diol

Details

• Internal ID: e0edc236-b616-4048-8dfa-43e83e54743a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S)-2-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-ene-1,2-diol
• SMILES (Canonical): CC(=CCCC(CO)(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4(C)C)O)C)C)C)O)C
• SMILES (Isomeric): CC(=CCC[C@@](CO)([C@H]1CC[C@@]2([C@@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C)O)C
• InChI: InChI=1S/C30H52O3/c1-20(2)9-8-15-30(33,19-31)22-12-17-28(6)21(22)10-11-24-27(5)16-14-25(32)26(3,4)23(27)13-18-29(24,28)7/h9,21-25,31-33H,8,10-19H2,1-7H3/t21-,22+,23+,24-,25+,27+,28-,29-,30-/m1/s1
• InChI Key: ARYNZYKWUXIZOG-AYHBXSNGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₂O₃
• Molecular Weight: 460.70 g/mol
• Exact Mass: 460.39164552 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 7.50
• Atomic LogP (AlogP): 6.50
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• BDBM50423991

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	-	0.5596	55.96%
Blood Brain Barrier	+	0.7635	76.35%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7028	70.28%
OATP2B1 inhibitior	-	0.5758	57.58%
OATP1B1 inhibitior	+	0.8618	86.18%
OATP1B3 inhibitior	+	0.9638	96.38%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6833	68.33%
BSEP inhibitior	+	0.8492	84.92%
P-glycoprotein inhibitior	-	0.6108	61.08%
P-glycoprotein substrate	-	0.8647	86.47%
CYP3A4 substrate	+	0.6719	67.19%
CYP2C9 substrate	-	0.7657	76.57%
CYP2D6 substrate	-	0.7779	77.79%
CYP3A4 inhibition	-	0.8018	80.18%
CYP2C9 inhibition	-	0.8394	83.94%
CYP2C19 inhibition	-	0.8972	89.72%
CYP2D6 inhibition	-	0.9410	94.10%
CYP1A2 inhibition	-	0.9158	91.58%
CYP2C8 inhibition	-	0.6177	61.77%
CYP inhibitory promiscuity	-	0.8153	81.53%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6912	69.12%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9317	93.17%
Skin irritation	-	0.5617	56.17%
Skin corrosion	-	0.9604	96.04%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6754	67.54%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.6734	67.34%
skin sensitisation	-	0.7516	75.16%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8009	80.09%
Acute Oral Toxicity (c)	III	0.6492	64.92%
Estrogen receptor binding	+	0.7851	78.51%
Androgen receptor binding	+	0.7374	73.74%
Thyroid receptor binding	+	0.6677	66.77%
Glucocorticoid receptor binding	+	0.7421	74.21%
Aromatase binding	+	0.7535	75.35%
PPAR gamma	+	0.6599	65.99%
Honey bee toxicity	-	0.6874	68.74%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9719	97.19%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	15200 nM	IC50	PMID: 23177789

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1937	Q92769	Histone deacetylase 2	93.70%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.52%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.47%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.00%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.67%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.45%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.39%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	86.72%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.12%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.18%	96.61%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.51%	82.69%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	82.05%	94.01%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.02%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.76%	92.94%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.73%	100.00%
CHEMBL1977	P11473	Vitamin D receptor	81.16%	99.43%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.14%	91.03%
CHEMBL2581	P07339	Cathepsin D	80.70%	98.95%
CHEMBL233	P35372	Mu opioid receptor	80.62%	97.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.15%	95.50%

Plants that contains it

• Coleostephus myconis
• Dahlia pinnata
• Gynostemma pentaphyllum
• Synotis alata

Cross-Links

• PubChem: 60201377
• NPASS: NPC13554
• ChEMBL: CHEMBL2313414