(3beta)-3-[(O-alpha-L-Arabinopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->6)-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl)oxy]olean-12-en-28-oic acid

Details

• Internal ID: e241e8d4-75af-4bcd-9ea9-7d21c03d7b3a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxy-3-[(2S,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-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)COC7C(C(C(CO7)O)O)OC8C(C(C(CO8)O)O)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)C)C2C1)C)C(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O
• InChI: InChI=1S/C52H84O21/c1-47(2)14-16-52(46(64)65)17-15-50(6)23(24(52)18-47)8-9-30-49(5)12-11-31(48(3,4)29(49)10-13-51(30,50)7)71-45-41(73-43-39(63)36(60)34(58)27(19-53)69-43)37(61)35(59)28(70-45)22-68-44-40(33(57)26(55)21-67-44)72-42-38(62)32(56)25(54)20-66-42/h8,24-45,53-63H,9-22H2,1-7H3,(H,64,65)/t24-,25-,26-,27+,28+,29-,30+,31-,32-,33-,34+,35+,36-,37-,38+,39+,40+,41+,42-,43-,44-,45-,49-,50+,51+,52-/m0/s1
• InChI Key: KFZSKNXELYGVEA-IKDIIPBYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₄O₂₁
• Molecular Weight: 1045.20 g/mol
• Exact Mass: 1044.55050968 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.19
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 11

Synonyms

• (3beta)-3-[(O-alpha-L-Arabinopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->6)-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl)oxy]olean-12-en-28-oic acid
• 189161-87-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8866	88.66%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7138	71.38%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.7674	76.74%
P-glycoprotein inhibitior	+	0.7485	74.85%
P-glycoprotein substrate	-	0.7383	73.83%
CYP3A4 substrate	+	0.7288	72.88%
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	+	0.6965	69.65%
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	-	0.9029	90.29%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7298	72.98%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8486	84.86%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7984	79.84%
Androgen receptor binding	+	0.7324	73.24%
Thyroid receptor binding	-	0.5212	52.12%
Glucocorticoid receptor binding	+	0.6943	69.43%
Aromatase binding	+	0.6236	62.36%
PPAR gamma	+	0.7840	78.40%
Honey bee toxicity	-	0.7000	70.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6205	62.05%
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	97.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.49%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.65%	97.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.36%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.56%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.43%	97.36%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.35%	96.77%
CHEMBL5255	O00206	Toll-like receptor 4	86.88%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.45%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.40%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	84.62%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.83%	86.33%
CHEMBL2581	P07339	Cathepsin D	82.88%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	82.86%	95.93%
CHEMBL5028	O14672	ADAM10	82.49%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.66%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.18%	100.00%

Plants that contains it

• Albizia procera
• Pithecellobium dulce

Cross-Links

• PubChem: 46935013
• LOTUS: LTS0268256
• wikiData: Q105140636