[(3S,5S,10S,13S,14R,16R,17R)-17-[(2S,3R,4S)-3,4-dihydroxy-4-[(2S,3S)-3-methyl-2-propan-2-yloxiran-2-yl]butan-2-yl]-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-16-yl] acetate

Details

• Internal ID: 13b06360-2d6e-489d-aa30-a590cdd66a1b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3S,5S,10S,13S,14R,16R,17R)-17-[(2S,3R,4S)-3,4-dihydroxy-4-[(2S,3S)-3-methyl-2-propan-2-yloxiran-2-yl]butan-2-yl]-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-16-yl] acetate
• SMILES (Canonical): CC1C(O1)(C(C)C)C(C(C(C)C2C(CC3C2(CC=C4C3=CCC5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)O)C)C)OC(=O)C)O)O
• SMILES (Isomeric): C[C@H]1[C@@](O1)([C@H]([C@@H]([C@@H](C)[C@H]2[C@@H](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)OC(=O)C)O)O)C(C)C
• InChI: InChI=1S/C37H58O11/c1-17(2)37(19(4)48-37)33(44)29(40)18(3)28-26(45-20(5)39)15-25-23-9-8-21-14-22(10-12-35(21,6)24(23)11-13-36(25,28)7)46-34-32(43)31(42)30(41)27(16-38)47-34/h9,11,17-19,21-22,25-34,38,40-44H,8,10,12-16H2,1-7H3/t18-,19-,21-,22-,25-,26+,27+,28-,29+,30+,31-,32+,33-,34+,35-,36-,37+/m0/s1
• InChI Key: CNLXKTWNTITWTJ-WTBOBHHVSA-N
• Popularity: 0 references 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: 2.40
• Atomic LogP (AlogP): 2.38
• 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	+	0.8542	85.42%
Caco-2	-	0.8573	85.73%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8533	85.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8125	81.25%
OATP1B3 inhibitior	-	0.2467	24.67%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.7405	74.05%
P-glycoprotein inhibitior	+	0.7155	71.55%
P-glycoprotein substrate	+	0.5797	57.97%
CYP3A4 substrate	+	0.7363	73.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8875	88.75%
CYP3A4 inhibition	-	0.9351	93.51%
CYP2C9 inhibition	-	0.7745	77.45%
CYP2C19 inhibition	-	0.8969	89.69%
CYP2D6 inhibition	-	0.9286	92.86%
CYP1A2 inhibition	-	0.8377	83.77%
CYP2C8 inhibition	+	0.6986	69.86%
CYP inhibitory promiscuity	-	0.8853	88.53%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6377	63.77%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9204	92.04%
Skin irritation	-	0.5738	57.38%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7688	76.88%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.6851	68.51%
skin sensitisation	-	0.8811	88.11%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.5613	56.13%
Acute Oral Toxicity (c)	III	0.5895	58.95%
Estrogen receptor binding	+	0.7665	76.65%
Androgen receptor binding	+	0.6961	69.61%
Thyroid receptor binding	-	0.5262	52.62%
Glucocorticoid receptor binding	+	0.6378	63.78%
Aromatase binding	+	0.6079	60.79%
PPAR gamma	+	0.6709	67.09%
Honey bee toxicity	-	0.6795	67.95%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9721	97.21%

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	99.33%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.74%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.73%	97.25%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	98.58%	94.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.30%	94.45%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	96.47%	94.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.46%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.80%	98.95%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	92.53%	94.97%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.12%	85.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.29%	93.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.89%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.82%	100.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.39%	98.05%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	87.03%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.99%	89.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.83%	89.05%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.77%	94.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.66%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.81%	89.67%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	83.63%	97.53%
CHEMBL5028	O14672	ADAM10	83.51%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	83.30%	92.50%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.87%	82.50%
CHEMBL237	P41145	Kappa opioid receptor	82.76%	98.10%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.72%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.11%	91.07%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.84%	96.61%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.79%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.40%	95.89%

Plants that contains it

• Gymnanthemum amygdalinum

Cross-Links

• PubChem: 163059666
• LOTUS: LTS0017391
• wikiData: Q104965975