(3S,5R,8R,9R,10R,13R,14R,17S)-17-[4-[(2R)-3,3-dimethyloxiran-2-yl]but-1-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]phenanthren-3-ol

Details

• Internal ID: 08c229ee-5c37-4fa3-8713-2ac78a5b3d83
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,5R,8R,9R,10R,13R,14R,17S)-17-[4-[(2R)-3,3-dimethyloxiran-2-yl]but-1-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]phenanthren-3-ol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1O)C)CCC4C3(CCC4C(=C)CCC5C(O5)(C)C)C)C)C
• SMILES (Isomeric): C[C@@]12CC[C@@H]([C@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C(=C)CC[C@@H]5C(O5)(C)C
• InChI: InChI=1S/C30H50O2/c1-19(9-12-25-27(4,5)32-25)20-13-17-29(7)21(20)10-11-23-28(6)16-15-24(31)26(2,3)22(28)14-18-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21-,22+,23-,24+,25-,28+,29-,30-/m1/s1
• InChI Key: ILQUAQTXYDCHSY-WYAOSOTQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₂
• Molecular Weight: 442.70 g/mol
• Exact Mass: 442.381080833 g/mol
• Topological Polar Surface Area (TPSA): 32.80 Ų
• XlogP: 8.70
• Atomic LogP (AlogP): 7.55
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	-	0.5495	54.95%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4451	44.51%
OATP2B1 inhibitior	-	0.7157	71.57%
OATP1B1 inhibitior	+	0.9172	91.72%
OATP1B3 inhibitior	+	0.9132	91.32%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.5726	57.26%
P-glycoprotein inhibitior	-	0.6285	62.85%
P-glycoprotein substrate	-	0.8231	82.31%
CYP3A4 substrate	+	0.6816	68.16%
CYP2C9 substrate	-	0.6206	62.06%
CYP2D6 substrate	-	0.7163	71.63%
CYP3A4 inhibition	-	0.6383	63.83%
CYP2C9 inhibition	-	0.6865	68.65%
CYP2C19 inhibition	-	0.5146	51.46%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.7036	70.36%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.6539	65.39%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6306	63.06%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.8921	89.21%
Skin irritation	-	0.5574	55.74%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7300	73.00%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.5328	53.28%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7898	78.98%
Acute Oral Toxicity (c)	III	0.7137	71.37%
Estrogen receptor binding	+	0.7168	71.68%
Androgen receptor binding	+	0.7825	78.25%
Thyroid receptor binding	+	0.5975	59.75%
Glucocorticoid receptor binding	+	0.7876	78.76%
Aromatase binding	+	0.6603	66.03%
PPAR gamma	+	0.5292	52.92%
Honey bee toxicity	-	0.7284	72.84%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9843	98.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL218	P21554	Cannabinoid CB1 receptor	98.74%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.38%	96.09%
CHEMBL233	P35372	Mu opioid receptor	91.92%	97.93%
CHEMBL4302	P08183	P-glycoprotein 1	90.32%	92.98%
CHEMBL240	Q12809	HERG	89.70%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.38%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.91%	97.09%
CHEMBL325	Q13547	Histone deacetylase 1	87.13%	95.92%
CHEMBL1937	Q92769	Histone deacetylase 2	85.98%	94.75%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.94%	89.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.53%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.38%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.83%	97.25%
CHEMBL3524	P56524	Histone deacetylase 4	83.12%	92.97%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.04%	95.89%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	82.67%	92.38%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.50%	82.69%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.17%	97.53%
CHEMBL237	P41145	Kappa opioid receptor	82.08%	98.10%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.38%	94.00%

Plants that contains it

• Aglaia odorata
• Camellia sasanqua

Cross-Links

• PubChem: 11797479
• NPASS: NPC52484
• LOTUS: LTS0045740
• wikiData: Q105115395