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

Details

• Internal ID: 7c8e0eec-ff31-4b43-bf58-add057d128a8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-6-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
• SMILES (Canonical): CC(=C)CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)O)C)C)O)C)O
• SMILES (Isomeric): CC(=C)CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)O)C)O
• InChI: InChI=1S/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h20-25,31-33H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25-,27-,28+,29+,30-/m0/s1
• InChI Key: OKPIBBOLEJSSTE-HKUCOEKDSA-N
• Popularity: 1 reference 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: 7.30
• Atomic LogP (AlogP): 6.50
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• BDBM50423988

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	-	0.6183	61.83%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5551	55.51%
OATP2B1 inhibitior	-	0.5712	57.12%
OATP1B1 inhibitior	+	0.8543	85.43%
OATP1B3 inhibitior	+	0.8754	87.54%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.5802	58.02%
P-glycoprotein inhibitior	-	0.6716	67.16%
P-glycoprotein substrate	-	0.7147	71.47%
CYP3A4 substrate	+	0.6966	69.66%
CYP2C9 substrate	-	0.5811	58.11%
CYP2D6 substrate	-	0.7340	73.40%
CYP3A4 inhibition	-	0.7308	73.08%
CYP2C9 inhibition	-	0.9157	91.57%
CYP2C19 inhibition	-	0.8603	86.03%
CYP2D6 inhibition	-	0.9534	95.34%
CYP1A2 inhibition	-	0.9402	94.02%
CYP2C8 inhibition	-	0.5882	58.82%
CYP inhibitory promiscuity	-	0.6170	61.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6612	66.12%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.9106	91.06%
Skin irritation	+	0.5396	53.96%
Skin corrosion	-	0.9513	95.13%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4132	41.32%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.7473	74.73%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8383	83.83%
Acute Oral Toxicity (c)	I	0.7152	71.52%
Estrogen receptor binding	+	0.6845	68.45%
Androgen receptor binding	+	0.7275	72.75%
Thyroid receptor binding	+	0.6390	63.90%
Glucocorticoid receptor binding	+	0.7002	70.02%
Aromatase binding	+	0.7555	75.55%
PPAR gamma	+	0.6228	62.28%
Honey bee toxicity	-	0.6581	65.81%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9952	99.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.31%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	97.56%	82.69%
CHEMBL2996	Q05655	Protein kinase C delta	97.02%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.97%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.88%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.98%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	90.37%	95.93%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	89.83%	95.58%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.13%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.16%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.23%	92.94%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.71%	97.21%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	85.08%	95.42%
CHEMBL206	P03372	Estrogen receptor alpha	84.70%	97.64%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.66%	100.00%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	82.61%	92.50%
CHEMBL1951	P21397	Monoamine oxidase A	82.17%	91.49%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	81.82%	94.01%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.39%	95.89%
CHEMBL3045	P05771	Protein kinase C beta	80.91%	97.63%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.08%	100.00%

Plants that contains it

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

Cross-Links

• PubChem: 71719758
• NPASS: NPC3403