(2R,3S,4S,5S,6S)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9R,10S,12aS,14aR,14bS)-9,10-dihydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3S,4R,5R,6S)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: ff373467-a87c-48a2-be99-f65be1468f63
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2R,3S,4S,5S,6S)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9R,10S,12aS,14aR,14bS)-9,10-dihydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3S,4R,5R,6S)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC3C(C(C(C(O3)C)O)O)O)OC4C(C(C(OC4OC5CCC6(C(C5(C)CO)CCC7(C6CC=C8C7(CCC9(C8CC(C(C9O)O)(C)C)C)C)C)C)C(=O)O)O)O)CO)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@@H]([C@@H](O1)O[C@@H]2[C@@H]([C@@H](O[C@@H]([C@H]2O[C@H]3[C@H]([C@H]([C@H]([C@H](O3)C)O)O)O)O[C@H]4[C@H]([C@@H]([C@@H](O[C@@H]4O[C@H]5CC[C@@]6([C@H]([C@@]5(C)CO)CC[C@@]7([C@@H]6CC=C8[C@]7(CC[C@@]9([C@H]8CC([C@@H]([C@@H]9O)O)(C)C)C)C)C)C)C(=O)O)O)O)CO)O)O)O)O
• InChI: InChI=1S/C54H88O23/c1-21-29(57)32(60)36(64)45(70-21)74-38-31(59)25(19-55)72-48(41(38)77-46-37(65)33(61)30(58)22(2)71-46)76-40-35(63)34(62)39(44(68)69)75-47(40)73-28-13-14-51(6)26(52(28,7)20-56)12-15-54(9)27(51)11-10-23-24-18-49(3,4)42(66)43(67)50(24,5)16-17-53(23,54)8/h10,21-22,24-43,45-48,55-67H,11-20H2,1-9H3,(H,68,69)/t21-,22-,24+,25+,26-,27-,28+,29+,30+,31-,32+,33+,34+,35+,36+,37+,38-,39-,40+,41+,42-,43+,45+,46+,47+,48-,50-,51-,52-,53-,54-/m1/s1
• InChI Key: LICVUYJOGINHJA-RJLFAMORSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₈O₂₃
• Molecular Weight: 1105.30 g/mol
• Exact Mass: 1104.57163905 g/mol
• Topological Polar Surface Area (TPSA): 374.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -1.47
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7499	74.99%
Caco-2	-	0.8969	89.69%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8758	87.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8449	84.49%
OATP1B3 inhibitior	-	0.5977	59.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.8842	88.42%
P-glycoprotein inhibitior	+	0.7486	74.86%
P-glycoprotein substrate	-	0.6151	61.51%
CYP3A4 substrate	+	0.7355	73.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9589	95.89%
CYP2C9 inhibition	-	0.8763	87.63%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	+	0.7676	76.76%
CYP inhibitory promiscuity	-	0.9423	94.23%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6313	63.13%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7405	74.05%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.7561	75.61%
Acute Oral Toxicity (c)	III	0.7822	78.22%
Estrogen receptor binding	+	0.8055	80.55%
Androgen receptor binding	+	0.7440	74.40%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7424	74.24%
Aromatase binding	+	0.6435	64.35%
PPAR gamma	+	0.8122	81.22%
Honey bee toxicity	-	0.7128	71.28%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9603	96.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3714130	P46095	G-protein coupled receptor 6	97.54%	97.36%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.48%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.86%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.51%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.81%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.08%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.14%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.94%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.82%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.85%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.53%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.44%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.34%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.30%	94.45%

Plants that contains it

• Lupinus angustifolius

Cross-Links

• PubChem: 163030439
• LOTUS: LTS0112049
• wikiData: Q105152119