[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,10S,12aR,14bR)-10-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Details

• Internal ID: a8206044-b386-4d25-a4d4-1db91513460f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,10S,12aR,14bR)-10-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(CO6)O)OC7C(C(C(C(O7)CO)O)O)O)O)C)C)C2C1)C)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C(C1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O[C@@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O
• InChI: InChI=1S/C47H76O17/c1-42(2)14-16-47(41(58)64-40-35(56)33(54)31(52)26(20-49)61-40)17-15-45(6)22(23(47)18-42)8-9-28-44(5)12-11-29(43(3,4)27(44)10-13-46(28,45)7)62-38-36(57)37(24(50)21-59-38)63-39-34(55)32(53)30(51)25(19-48)60-39/h8,23-40,48-57H,9-21H2,1-7H3/t23-,24+,25-,26-,27?,28-,29+,30-,31-,32+,33+,34-,35-,36-,37+,38+,39-,40+,44+,45-,46-,47+/m1/s1
• InChI Key: LCMURMAVBYASPU-REEYWUBFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₇
• Molecular Weight: 913.10 g/mol
• Exact Mass: 912.50825095 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 0.78
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• Guaiacin B
• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,10S,12aR,14bR)-10-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• Oleanolic acid-3-O-(glucopyranosyl-1-3-arabinopyranosyl)-28-1-glucopyranosyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8843	88.43%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	0.8786	87.86%
OATP1B1 inhibitior	-	0.3391	33.91%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.6161	61.61%
P-glycoprotein inhibitior	+	0.7533	75.33%
P-glycoprotein substrate	-	0.8010	80.10%
CYP3A4 substrate	+	0.7248	72.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
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	+	0.6504	65.04%
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	-	0.9052	90.52%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7278	72.78%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9875	98.75%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9122	91.22%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7683	76.83%
Androgen receptor binding	+	0.7316	73.16%
Thyroid receptor binding	-	0.5677	56.77%
Glucocorticoid receptor binding	+	0.7144	71.44%
Aromatase binding	+	0.6187	61.87%
PPAR gamma	+	0.7769	77.69%
Honey bee toxicity	-	0.6811	68.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5405	54.05%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.31%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.84%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.99%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.85%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.45%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.23%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.53%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	83.97%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.84%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.65%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.95%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.85%	94.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.54%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	80.09%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.04%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.01%	86.33%

Plants that contains it

• Guaiacum officinale
• Ilex paraguariensis

Cross-Links

• PubChem: 196359
• LOTUS: LTS0037706
• wikiData: Q104667360