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

Details

• Internal ID: bd2e358a-6b53-4c8c-b186-bc481b0b847c
• 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] (2R,4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1-methylidene-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(CO6)O)O)O)C)C)C2C1=C)C)C(=O)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O)O)C)C)[C@@H]2C1=C)C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C41H64O13/c1-20-9-14-41(36(50)54-35-33(49)31(47)30(46)24(17-42)52-35)16-15-39(5)22(28(41)21(20)2)7-8-26-37(3)12-11-27(53-34-32(48)29(45)23(44)18-51-34)38(4,19-43)25(37)10-13-40(26,39)6/h7,20,23-35,42-49H,2,8-19H2,1,3-6H3/t20-,23+,24-,25-,26-,27+,28+,29+,30-,31+,32-,33-,34+,35+,37+,38+,39-,40-,41+/m1/s1
• InChI Key: LJCUOMZSVKPSBW-PAUAZMGASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₄O₁₃
• Molecular Weight: 764.90 g/mol
• Exact Mass: 764.43469209 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.70
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• 356785-73-4
• Ursa-12,19(29)-dien-28-oic acid, 3-(alpha-L-arabinopyranosyloxy)-23-hydroxy-, beta-D-glucopyranosyl ester, (3beta,4alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7135	71.35%
Caco-2	-	0.8806	88.06%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7934	79.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8319	83.19%
OATP1B3 inhibitior	-	0.3786	37.86%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	-	0.4572	45.72%
P-glycoprotein inhibitior	+	0.7376	73.76%
P-glycoprotein substrate	-	0.5740	57.40%
CYP3A4 substrate	+	0.7368	73.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.8913	89.13%
CYP2C9 inhibition	-	0.9110	91.10%
CYP2C19 inhibition	-	0.8993	89.93%
CYP2D6 inhibition	-	0.9474	94.74%
CYP1A2 inhibition	-	0.8888	88.88%
CYP2C8 inhibition	+	0.7271	72.71%
CYP inhibitory promiscuity	-	0.9715	97.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6497	64.97%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9118	91.18%
Skin irritation	-	0.5327	53.27%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7497	74.97%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9024	90.24%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7791	77.91%
Acute Oral Toxicity (c)	III	0.7014	70.14%
Estrogen receptor binding	+	0.7361	73.61%
Androgen receptor binding	+	0.7464	74.64%
Thyroid receptor binding	-	0.5686	56.86%
Glucocorticoid receptor binding	+	0.6452	64.52%
Aromatase binding	+	0.6178	61.78%
PPAR gamma	+	0.7081	70.81%
Honey bee toxicity	-	0.7080	70.80%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6750	67.50%
Fish aquatic toxicity	+	0.9590	95.90%

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	97.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.38%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.58%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.46%	97.36%
CHEMBL2581	P07339	Cathepsin D	87.28%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.55%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.98%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.77%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.77%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.52%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.48%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.43%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.39%	92.94%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.04%	91.07%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.58%	91.24%
CHEMBL5028	O14672	ADAM10	81.41%	97.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.95%	86.92%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.74%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.28%	95.89%

Plants that contains it

• Sanguisorba officinalis

Cross-Links

• PubChem: 11104682
• LOTUS: LTS0145092
• wikiData: Q105152501