(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,4S,7R,8S,9S,10S,12R,13R,16R,17S,18R)-16-(acetyloxy)-2-((acetyloxy)methyl)-10-hydroxy-9,13,17-trimethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-6-oxo-5-oxapentacyclo(10.8.0.0^(2,9).0^(4,8).0^(13,18))icos-1(20)-ene-17-carboxylate

Details

• Internal ID: 8edf2c34-2699-4c50-8530-ff581e82c19d
• 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] (2S,4S,7R,8S,9S,10S,12R,13R,16R,17S,18R)-16-acetyloxy-2-(acetyloxymethyl)-10-hydroxy-9,13,17-trimethyl-7-(4-methyl-2-oxopent-3-enyl)-6-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-1(20)-ene-17-carboxylate
• SMILES (Canonical): CC(=CC(=O)CC1C2C(CC3(C2(C(CC4C3=CCC5C4(CCC(C5(C)C(=O)OC6C(C(C(C(O6)CO)O)O)O)OC(=O)C)C)O)C)COC(=O)C)OC1=O)C
• SMILES (Isomeric): CC(=CC(=O)C[C@@H]1[C@@H]2[C@H](C[C@]3([C@]2([C@H](C[C@H]4C3=CC[C@@H]5[C@@]4(CC[C@H]([C@@]5(C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)OC(=O)C)C)O)C)COC(=O)C)OC1=O)C
• InChI: InChI=1S/C40H56O15/c1-18(2)12-21(44)13-22-30-25(53-34(22)49)15-40(17-51-19(3)42)23-8-9-27-37(5,24(23)14-28(45)39(30,40)7)11-10-29(52-20(4)43)38(27,6)36(50)55-35-33(48)32(47)31(46)26(16-41)54-35/h8,12,22,24-33,35,41,45-48H,9-11,13-17H2,1-7H3/t22-,24+,25+,26-,27-,28+,29-,30-,31-,32+,33-,35+,37-,38+,39+,40+/m1/s1
• InChI Key: CNBPSPDNZJNBAZ-RWOCPONYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₆O₁₅
• Molecular Weight: 776.90 g/mol
• Exact Mass: 776.36192108 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 15
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• BDBM50269529
• AKOS040763071
• (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,4S,7R,8S,9S,10S,12R,13R,16R,17S,18R)-16-(acetyloxy)-2-[(acetyloxy)methyl]-10-hydroxy-9,13,17-trimethyl-7-(4-methyl-2-oxopent-3-en-1-yl)-6-oxo-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-1(20)-ene-17-carboxylate
• 215160-96-6
• 3??,30-Diacetoxy-12??-hydroxy-23-oxoeupha-7,24-dien-21,16??-olid-28-oic acid 28-O-??-D-glucopyranosyl ester
• 3alpha,30-Diacetoxy-12alpha-hydroxy-21,23-dioxo-16beta,21-epoxy-5alpha-eupha-7,24-diene-28-oic acid beta-D-glucopyranosyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8427	84.27%
Caco-2	-	0.8686	86.86%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8733	87.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8104	81.04%
OATP1B3 inhibitior	+	0.8381	83.81%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.8946	89.46%
P-glycoprotein inhibitior	+	0.7857	78.57%
P-glycoprotein substrate	+	0.6057	60.57%
CYP3A4 substrate	+	0.7319	73.19%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8888	88.88%
CYP3A4 inhibition	-	0.8187	81.87%
CYP2C9 inhibition	-	0.8372	83.72%
CYP2C19 inhibition	-	0.9259	92.59%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.9133	91.33%
CYP2C8 inhibition	+	0.7100	71.00%
CYP inhibitory promiscuity	-	0.9476	94.76%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4689	46.89%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9142	91.42%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9368	93.68%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6791	67.91%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6601	66.01%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7445	74.45%
Acute Oral Toxicity (c)	III	0.6742	67.42%
Estrogen receptor binding	+	0.8149	81.49%
Androgen receptor binding	+	0.7543	75.43%
Thyroid receptor binding	-	0.5149	51.49%
Glucocorticoid receptor binding	+	0.7978	79.78%
Aromatase binding	+	0.6567	65.67%
PPAR gamma	+	0.7870	78.70%
Honey bee toxicity	-	0.6841	68.41%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9692	96.92%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL204	P00734	Thrombin	70 nM; 70 nM	IC50; IC50	PMID: 23511021; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.48%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.12%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.93%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.09%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.88%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.80%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.75%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.32%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.57%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.27%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.56%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.03%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	87.01%	92.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.33%	97.28%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	84.40%	91.65%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.41%	96.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.86%	97.14%
CHEMBL5028	O14672	ADAM10	82.57%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.47%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.04%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.63%	95.89%

Plants that contains it

• Lantana camara

Cross-Links

• PubChem: 10819005
• NPASS: NPC47113
• ChEMBL: CHEMBL449122
• LOTUS: LTS0149831
• wikiData: Q104965576