[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R)-2-[(3S,5S,10S,13R,14R,17R)-10,13-dimethyl-3-[(2S,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]-4-[(2S,3R)-3-methyl-2-propan-2-yloxiran-2-yl]butanoate

Details

• Internal ID: 79b22290-42c3-4c66-b2fd-0fc61d1bd28d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R)-2-[(3S,5S,10S,13R,14R,17R)-10,13-dimethyl-3-[(2S,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]-4-[(2S,3R)-3-methyl-2-propan-2-yloxiran-2-yl]butanoate
• SMILES (Canonical): CC1C(O1)(CCC(C2CCC3C2(CC=C4C3=CCC5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)O)C)C)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C(C)C
• SMILES (Isomeric): C[C@@H]1[C@](O1)(CC[C@H]([C@H]2CC[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)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C(C)C
• InChI: InChI=1S/C41H64O14/c1-19(2)41(20(3)55-41)15-11-24(36(50)54-38-35(49)33(47)31(45)29(18-43)53-38)26-9-8-25-23-7-6-21-16-22(10-13-39(21,4)27(23)12-14-40(25,26)5)51-37-34(48)32(46)30(44)28(17-42)52-37/h7,12,19-22,24-26,28-35,37-38,42-49H,6,8-11,13-18H2,1-5H3/t20-,21+,22+,24-,25+,26-,28-,29-,30-,31-,32+,33+,34-,35-,37-,38+,39+,40+,41+/m1/s1
• InChI Key: NUNIWGIXMAKESY-ORIHFSQOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₄O₁₄
• Molecular Weight: 780.90 g/mol
• Exact Mass: 780.42960671 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.22
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7944	79.44%
Caco-2	-	0.8754	87.54%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8464	84.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8235	82.35%
OATP1B3 inhibitior	-	0.2610	26.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6026	60.26%
BSEP inhibitior	+	0.5672	56.72%
P-glycoprotein inhibitior	+	0.7207	72.07%
P-glycoprotein substrate	+	0.5842	58.42%
CYP3A4 substrate	+	0.7293	72.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8809	88.09%
CYP3A4 inhibition	-	0.9599	95.99%
CYP2C9 inhibition	-	0.8062	80.62%
CYP2C19 inhibition	-	0.8844	88.44%
CYP2D6 inhibition	-	0.9285	92.85%
CYP1A2 inhibition	-	0.8596	85.96%
CYP2C8 inhibition	+	0.6122	61.22%
CYP inhibitory promiscuity	-	0.9162	91.62%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6227	62.27%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9147	91.47%
Skin irritation	-	0.6239	62.39%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4271	42.71%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6386	63.86%
skin sensitisation	-	0.8779	87.79%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.5970	59.70%
Acute Oral Toxicity (c)	III	0.5772	57.72%
Estrogen receptor binding	+	0.7850	78.50%
Androgen receptor binding	+	0.7292	72.92%
Thyroid receptor binding	-	0.5749	57.49%
Glucocorticoid receptor binding	+	0.5914	59.14%
Aromatase binding	+	0.5975	59.75%
PPAR gamma	+	0.6943	69.43%
Honey bee toxicity	-	0.6544	65.44%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	+	0.9652	96.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.76%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.20%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.18%	97.25%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	97.53%	94.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.03%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.51%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.07%	96.21%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.74%	93.56%
CHEMBL2581	P07339	Cathepsin D	89.51%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	89.01%	92.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.16%	94.08%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.06%	98.05%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	87.05%	94.97%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.95%	96.47%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.35%	94.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.06%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.74%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.66%	100.00%
CHEMBL237	P41145	Kappa opioid receptor	84.98%	98.10%
CHEMBL340	P08684	Cytochrome P450 3A4	83.96%	91.19%
CHEMBL226	P30542	Adenosine A1 receptor	83.73%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.49%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.85%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.23%	89.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.97%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.34%	82.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.12%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.07%	86.33%

Plants that contains it

• Gymnanthemum amygdalinum

Cross-Links

• PubChem: 162941860
• LOTUS: LTS0037246
• wikiData: Q105185954