3beta-[2-O-(2-O-alpha-L-Rhamnopyranosyl-beta-D-galactopyranosyl)-beta-D-glucopyranuronosyloxy]-21alpha-(alpha-L-arabinopyranosyloxy)oleana-12-ene-22beta,24-diol

Details

• Internal ID: 3e656636-cdfb-40b1-a399-5ae51ebb8bee
• 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,10S,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(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-3,4-dihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC5(C(C4(C)CO)CCC6(C5CC=C7C6(CCC8(C7CC(C(C8O)OC9C(C(C(CO9)O)O)O)(C)C)C)C)C)C)C(=O)O)O)O)CO)O)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]([C@H](O[C@H]2O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3O[C@H]4CC[C@]5([C@H]([C@@]4(C)CO)CC[C@@]6([C@@H]5CC=C7[C@]6(CC[C@@]8([C@H]7CC([C@@H]([C@H]8O)O[C@H]9[C@@H]([C@H]([C@H](CO9)O)O)O)(C)C)C)C)C)C)C(=O)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C53H86O23/c1-21-29(57)32(60)37(65)45(70-21)74-39-33(61)31(59)25(18-54)71-46(39)75-40-35(63)34(62)38(43(67)68)73-47(40)72-28-12-13-50(5)26(51(28,6)20-55)11-14-53(8)27(50)10-9-22-23-17-48(2,3)42(41(66)49(23,4)15-16-52(22,53)7)76-44-36(64)30(58)24(56)19-69-44/h9,21,23-42,44-47,54-66H,10-20H2,1-8H3,(H,67,68)/t21-,23-,24-,25+,26+,27+,28-,29-,30-,31-,32+,33-,34-,35-,36+,37+,38-,39+,40+,41+,42+,44-,45-,46-,47+,49+,50-,51+,52+,53+/m0/s1
• InChI Key: SMXKPPHSZHNBEF-QPNAEPOWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₃
• Molecular Weight: 1091.20 g/mol
• Exact Mass: 1090.55598899 g/mol
• Topological Polar Surface Area (TPSA): 374.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -1.86
• 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	+	0.7891	78.91%
Caco-2	-	0.9014	90.14%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8200	82.00%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8879	88.79%
P-glycoprotein inhibitior	+	0.7477	74.77%
P-glycoprotein substrate	-	0.5142	51.42%
CYP3A4 substrate	+	0.7373	73.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.7873	78.73%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9015	90.15%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8017	80.17%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9113	91.13%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8013	80.13%
Androgen receptor binding	+	0.7419	74.19%
Thyroid receptor binding	+	0.5285	52.85%
Glucocorticoid receptor binding	+	0.7553	75.53%
Aromatase binding	+	0.6534	65.34%
PPAR gamma	+	0.8177	81.77%
Honey bee toxicity	-	0.6967	69.67%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9411	94.11%

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	98.36%	97.36%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.62%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.71%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.60%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.48%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.64%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.70%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.48%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.21%	91.07%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.91%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.15%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.12%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.76%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	82.28%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.03%	95.89%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	80.90%	92.78%
CHEMBL5028	O14672	ADAM10	80.37%	97.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.37%	94.75%

Plants that contains it

• Lupinus oreophilus
• Pogostemon cablin

Cross-Links

• PubChem: 101260285
• NPASS: NPC264796
• LOTUS: LTS0233199
• wikiData: Q105256225