2-Butenoic acid, 2-methyl-, (3R,4R,4aR,5R,6aS,6bR,10S,12aR,14aS,16S)-10-[[O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->3)-O-[beta-D-galactopyranosyl-(1->2)]-beta-D-glucopyranosyl]oxy]octadecahydro-4,5,16-trihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-2H,5H-14a,4a-(epoxymethano)picen-3-yl ester, (2E)-

Details

• Internal ID: 9225a110-7c6a-47d8-850f-765b4965423d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(1R,2R,4S,5R,10S,13R,17S,21R,22R,23S)-10-[(2R,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,22,23-trihydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-21-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C23C(CC1(C)C)C4(CCC5C6(CCC(C(C6CCC5(C4(CC2O)C)C)(C)C)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)C)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)OC3O)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@@H]([C@]23[C@@H](C[C@]4([C@@]5(CCC6[C@@](C5CC[C@@]4(C2CC1(C)C)O[C@@H]3O)(CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)C)C)C)O)O
• InChI: InChI=1S/C59H96O26/c1-11-23(2)47(74)84-46-45(73)59-30(18-53(46,4)5)58(85-52(59)75)17-13-29-55(8)15-14-32(54(6,7)28(55)12-16-56(29,9)57(58,10)19-31(59)63)80-51-44(83-49-41(72)38(69)34(65)25(20-60)77-49)42(36(67)27(22-62)79-51)81-50-43(39(70)35(66)26(21-61)78-50)82-48-40(71)37(68)33(64)24(3)76-48/h11,24-46,48-52,60-73,75H,12-22H2,1-10H3/b23-11+/t24-,25+,26+,27+,28?,29?,30?,31+,32-,33-,34-,35-,36+,37+,38-,39-,40+,41+,42-,43+,44+,45-,46-,48-,49-,50-,51-,52-,55-,56+,57-,58-,59+/m0/s1
• InChI Key: QWKDHDNZUMSQQT-QVTHWRQPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₉₆O₂₆
• Molecular Weight: 1221.40 g/mol
• Exact Mass: 1220.61898316 g/mol
• Topological Polar Surface Area (TPSA): 413.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -2.55
• H-Bond Acceptor: 26
• H-Bond Donor: 15
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8124	81.24%
Caco-2	-	0.8734	87.34%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7880	78.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7918	79.18%
OATP1B3 inhibitior	+	0.8804	88.04%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9425	94.25%
P-glycoprotein inhibitior	+	0.7460	74.60%
P-glycoprotein substrate	+	0.5420	54.20%
CYP3A4 substrate	+	0.7387	73.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8731	87.31%
CYP3A4 inhibition	-	0.9173	91.73%
CYP2C9 inhibition	-	0.7907	79.07%
CYP2C19 inhibition	-	0.8740	87.40%
CYP2D6 inhibition	-	0.9302	93.02%
CYP1A2 inhibition	-	0.8866	88.66%
CYP2C8 inhibition	+	0.7188	71.88%
CYP inhibitory promiscuity	-	0.9378	93.78%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6031	60.31%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8992	89.92%
Skin irritation	-	0.5589	55.89%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.7378	73.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7729	77.29%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.8781	87.81%
skin sensitisation	-	0.8924	89.24%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7007	70.07%
Acute Oral Toxicity (c)	I	0.5040	50.40%
Estrogen receptor binding	+	0.7769	77.69%
Androgen receptor binding	+	0.7563	75.63%
Thyroid receptor binding	+	0.6013	60.13%
Glucocorticoid receptor binding	+	0.7773	77.73%
Aromatase binding	+	0.6686	66.86%
PPAR gamma	+	0.8081	80.81%
Honey bee toxicity	-	0.5963	59.63%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5155	51.55%
Fish aquatic toxicity	+	0.9565	95.65%

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	97.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.67%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.35%	97.36%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	92.67%	91.24%
CHEMBL221	P23219	Cyclooxygenase-1	92.16%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.20%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.00%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.46%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.86%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.17%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.13%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.81%	96.61%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.91%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.18%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	85.11%	92.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.58%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.13%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.90%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.94%	99.17%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.73%	93.04%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.73%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.66%	94.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.33%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.41%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.24%	91.19%

Plants that contains it

• Maesa lanceolata

Cross-Links

• PubChem: 6478539
• LOTUS: LTS0182503
• wikiData: Q105229234