(2R,3R,4S,5S,6R)-2-[[(4aS,5S,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-4a-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: a810f2e3-0a82-44f9-82cb-225f7831cac3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(4aS,5S,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-4a-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)COC7C(C(C(C(O7)COC8C(C(C(CO8)O)O)O)O)O)O)O)O)O)C)COC9C(C(C(C(O9)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@@H]([C@@]5([C@H]4CC(CC5)(C)C)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C53H88O22/c1-48(2)14-15-53(22-71-46-42(66)37(61)34(58)26(18-54)72-46)24(16-48)23-8-9-30-50(5)12-11-32(49(3,4)29(50)10-13-51(30,6)52(23,7)17-31(53)56)75-47-43(67)39(63)36(60)28(74-47)21-70-45-41(65)38(62)35(59)27(73-45)20-69-44-40(64)33(57)25(55)19-68-44/h8,24-47,54-67H,9-22H2,1-7H3/t24-,25+,26+,27+,28+,29-,30+,31-,32-,33-,34+,35+,36+,37-,38-,39-,40+,41+,42+,43+,44-,45+,46+,47-,50-,51+,52+,53+/m0/s1
• InChI Key: OWRMMXDXVOHFNG-PHZRQRTOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₈O₂₂
• Molecular Weight: 1077.30 g/mol
• Exact Mass: 1076.57672443 g/mol
• Topological Polar Surface Area (TPSA): 357.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.95
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7084	70.84%
Caco-2	-	0.8869	88.69%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7876	78.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7677	76.77%
OATP1B3 inhibitior	-	0.4367	43.67%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7600	76.00%
P-glycoprotein inhibitior	+	0.7463	74.63%
P-glycoprotein substrate	-	0.6893	68.93%
CYP3A4 substrate	+	0.7290	72.90%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9345	93.45%
CYP2C9 inhibition	-	0.8819	88.19%
CYP2C19 inhibition	-	0.8988	89.88%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.8923	89.23%
CYP2C8 inhibition	+	0.6880	68.80%
CYP inhibitory promiscuity	-	0.9600	96.00%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6252	62.52%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9017	90.17%
Skin irritation	-	0.6425	64.25%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8127	81.27%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8896	88.96%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.9387	93.87%
Acute Oral Toxicity (c)	III	0.7434	74.34%
Estrogen receptor binding	+	0.7969	79.69%
Androgen receptor binding	+	0.7302	73.02%
Thyroid receptor binding	+	0.5300	53.00%
Glucocorticoid receptor binding	+	0.7162	71.62%
Aromatase binding	+	0.6489	64.89%
PPAR gamma	+	0.7956	79.56%
Honey bee toxicity	-	0.7128	71.28%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.9174	91.74%

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	97.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.64%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.60%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.74%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	92.53%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.19%	96.61%
CHEMBL221	P23219	Cyclooxygenase-1	89.03%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.88%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.34%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.30%	96.21%
CHEMBL1937	Q92769	Histone deacetylase 2	86.42%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.14%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.23%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.23%	86.92%
CHEMBL2581	P07339	Cathepsin D	84.05%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.73%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.01%	92.62%
CHEMBL5028	O14672	ADAM10	81.91%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.56%	86.33%

Plants that contains it

• Gymnema sylvestre

Cross-Links

• PubChem: 10772484
• LOTUS: LTS0248102
• wikiData: Q105202220