3-O-[beta-D-glucopyranosyl-(1→3)-alpha-L-arabinopyranosyl]-oleanolic acid-28-O-[beta-D-glucopyranosyl] ester - Compound Card

3-O-[beta-D-glucopyranosyl-(1→3)-alpha-L-arabinopyranosyl]-oleanolic acid-28-O-[beta-D-glucopyranosyl] ester

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3-O-[beta-D-glucopyranosyl-(1→3)-alpha-L-arabinopyranosyl]-oleanolic acid-28-O-[beta-D-glucopyranosyl] ester

Family: Plantae - Zygophyllaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Triterpenoid Saponin

Canonical Smiles	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)CO[C@H]([C@@H]2O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@H]2O[C@@H](CO)[C@@H]([C@H]([C@@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)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-/m0/s1
InChIKey	LCMURMAVBYASPU-IXJRJNKYSA-N
Formula	C₄₇H₇₆O₁₇
HBA	17
HBD	10
MW	913.11
Rotatable Bonds	8
TPSA	274.75
LogP	0.78
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	64
Formal Charge	0
Fraction CSP3	0.94
Exact Mass	912.51
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fagonia indica	Zygophyllaceae	Plantae	66629

Showing of synonyms

Shaker K.H, Bernhardt M, et al. (1999). Triterpenoid saponins from Fagonia indica. Phytochemistry,1999,51(8),1049-53. [View] [PubMed]

Pubchem: 162930955

Zinc: ZINC000255225584

Nmrshiftdb2: 70058057

No compound-protein relationship available.

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCC7)CC7OC8CCCCO8

Level: 3

Mol. Weight: 913.11 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 913.11 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCC6)CC6OC7CCCCO7

Level: 2

Mol. Weight: 913.11 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 913.11 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 913.11 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 913.11 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 913.11 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 913.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.27
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1190.820
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 156443.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.800
Plasma Protein Binding: 96.67
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 1.450
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 31931020.690
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1.760
Log(P): 2.41
Log S: -3.36
Log(Vapor Pressure): -1051314.44
Melting Point: 286.3
pKa Acid: -7576.42
pKa Basic: -28.49

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7745