[3-[(3S,5S,10S,13S,14R)-16-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-[2-(2-hydroxypropan-2-yl)-3-methyloxiran-2-yl]butyl] acetate

Details

• Internal ID: 88a4a402-3cb7-4494-831d-a11e403510b6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [3-[(3S,5S,10S,13S,14R)-16-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-[2-(2-hydroxypropan-2-yl)-3-methyloxiran-2-yl]butyl] acetate
• SMILES (Canonical): CC1C(O1)(C(CC(C)C2C(CC3C2(CC=C4C3=CCC5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)OC(=O)C)C(C)(C)O
• SMILES (Isomeric): CC1C(O1)(C(CC(C)C2C(C[C@@H]3[C@@]2(CC=C4C3=CC[C@@H]5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)OC(=O)C)C(C)(C)O
• InChI: InChI=1S/C37H58O11/c1-18(14-28(45-20(3)39)37(19(2)48-37)34(4,5)44)29-26(40)16-25-23-9-8-21-15-22(10-12-35(21,6)24(23)11-13-36(25,29)7)46-33-32(43)31(42)30(41)27(17-38)47-33/h9,11,18-19,21-22,25-33,38,40-44H,8,10,12-17H2,1-7H3/t18?,19?,21-,22-,25-,26?,27+,28?,29?,30+,31-,32+,33+,35-,36-,37?/m0/s1
• InChI Key: NPBLCHFDSMHMJC-VRJKYSRSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₈O₁₁
• Molecular Weight: 678.80 g/mol
• Exact Mass: 678.39791266 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.53
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8799	87.99%
Caco-2	-	0.8629	86.29%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8279	82.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8252	82.52%
OATP1B3 inhibitior	+	0.7944	79.44%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	-	0.6133	61.33%
P-glycoprotein inhibitior	+	0.7395	73.95%
P-glycoprotein substrate	+	0.6217	62.17%
CYP3A4 substrate	+	0.7337	73.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8916	89.16%
CYP3A4 inhibition	-	0.8924	89.24%
CYP2C9 inhibition	-	0.7700	77.00%
CYP2C19 inhibition	-	0.9057	90.57%
CYP2D6 inhibition	-	0.9284	92.84%
CYP1A2 inhibition	-	0.8704	87.04%
CYP2C8 inhibition	+	0.6622	66.22%
CYP inhibitory promiscuity	-	0.9267	92.67%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6214	62.14%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9180	91.80%
Skin irritation	-	0.5295	52.95%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.6424	64.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.3663	36.63%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6048	60.48%
skin sensitisation	-	0.8825	88.25%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6095	60.95%
Acute Oral Toxicity (c)	III	0.5288	52.88%
Estrogen receptor binding	+	0.7650	76.50%
Androgen receptor binding	+	0.7253	72.53%
Thyroid receptor binding	-	0.5116	51.16%
Glucocorticoid receptor binding	+	0.6975	69.75%
Aromatase binding	+	0.6755	67.55%
PPAR gamma	+	0.6764	67.64%
Honey bee toxicity	-	0.6827	68.27%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9587	95.87%

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	99.71%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.75%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.05%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.94%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.85%	97.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	94.75%	94.23%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.49%	93.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.47%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.15%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.73%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.35%	100.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	88.23%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.08%	94.62%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	87.72%	94.97%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.99%	97.14%
CHEMBL237	P41145	Kappa opioid receptor	86.71%	98.10%
CHEMBL3401	O75469	Pregnane X receptor	86.70%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.63%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.70%	92.50%
CHEMBL2996	Q05655	Protein kinase C delta	85.57%	97.79%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.88%	94.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.65%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.22%	96.90%
CHEMBL4040	P28482	MAP kinase ERK2	82.51%	83.82%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.81%	89.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.43%	91.07%
CHEMBL5028	O14672	ADAM10	81.25%	97.50%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.56%	82.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.50%	95.71%

Plants that contains it

• Gymnanthemum amygdalinum

Cross-Links

• PubChem: 101683953
• LOTUS: LTS0168790
• wikiData: Q105182958