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

Details

• Internal ID: 519681b7-dfef-4a8b-9515-3cc1e6056623
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9S,10R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-10-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-4-hydroxy-6-(hydroxymethyl)-3,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)OC3C(C(C(C(O3)C)O)O)O)OC4C(C(C(OC4OC5CCC6(C(C5(C)CO)CCC7(C6CC=C8C7(CCC9(C8CC(C(C9O)OC1C(C(C(C(O1)C)O)O)O)(C)C)C)C)C)C)C(=O)O)O)O)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O[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@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)(C)C)C)C)C)C)C(=O)O)O)O)CO)O)O)O
• InChI: InChI=1S/C60H98O27/c1-22-31(63)34(66)39(71)50(78-22)83-43-27(20-61)81-53(46(42(43)74)85-51-40(72)35(67)32(64)23(2)79-51)86-45-38(70)37(69)44(49(76)77)84-54(45)82-30-14-15-57(7)28(58(30,8)21-62)13-16-60(10)29(57)12-11-25-26-19-55(4,5)48(47(75)56(26,6)17-18-59(25,60)9)87-52-41(73)36(68)33(65)24(3)80-52/h11,22-24,26-48,50-54,61-75H,12-21H2,1-10H3,(H,76,77)/t22-,23-,24-,26-,27+,28+,29+,30-,31-,32-,33-,34+,35+,36+,37-,38-,39+,40+,41+,42-,43-,44-,45+,46+,47+,48-,50-,51-,52-,53-,54+,56+,57-,58+,59+,60+/m0/s1
• InChI Key: KGWJIBWNFAZDHU-GEHNHPGZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₀H₉₈O₂₇
• Molecular Weight: 1251.40 g/mol
• Exact Mass: 1250.62954785 g/mol
• Topological Polar Surface Area (TPSA): 433.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.62
• H-Bond Acceptor: 26
• H-Bond Donor: 16
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7499	74.99%
Caco-2	-	0.8839	88.39%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8758	87.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8558	85.58%
OATP1B3 inhibitior	-	0.5977	59.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.9168	91.68%
P-glycoprotein inhibitior	+	0.7451	74.51%
P-glycoprotein substrate	-	0.5874	58.74%
CYP3A4 substrate	+	0.7301	73.01%
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	+	0.7768	77.68%
CYP inhibitory promiscuity	-	0.9423	94.23%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6313	63.13%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8991	89.91%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7967	79.67%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8625	86.25%
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	-	0.8067	80.67%
Acute Oral Toxicity (c)	III	0.7822	78.22%
Estrogen receptor binding	+	0.7970	79.70%
Androgen receptor binding	+	0.7421	74.21%
Thyroid receptor binding	+	0.6119	61.19%
Glucocorticoid receptor binding	+	0.7882	78.82%
Aromatase binding	+	0.6722	67.22%
PPAR gamma	+	0.8365	83.65%
Honey bee toxicity	-	0.7064	70.64%
Biodegradation	-	0.7500	75.00%
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	98.34%	97.36%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.83%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.67%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.39%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.08%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.53%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.39%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.33%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.96%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.63%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.43%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.13%	91.07%
CHEMBL2581	P07339	Cathepsin D	81.49%	98.95%

Plants that contains it

• Lupinus angustifolius

Cross-Links

• PubChem: 162877257
• LOTUS: LTS0118682
• wikiData: Q105141008