3-O-alpha-L-arabinopyranosyl-oleanolic acid 28-O-alpha-L-rhamnopy-ranosyl-(1→4)-beta-D-gentiobiosyl ester - Compound Card

3-O-alpha-L-arabinopyranosyl-oleanolic acid 28-O-alpha-L-rhamnopy-ranosyl-(1→4)-beta-D-gentiobiosyl ester

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3-O-alpha-L-arabinopyranosyl-oleanolic acid 28-O-alpha-L-rhamnopy-ranosyl-(1→4)-beta-D-gentiobiosyl ester

Structure
Zoomed Structure
  • Family: Plantae - Araliaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Triterpenoid Saponin
Canonical Smiles OCC1O[C@@](O)(OCC2O[C@H](O)[C@H](C([C@H]2O)O)O)[C@H](C([C@]1(O)C1(O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)OC(=O)[C@]12CC[C@@]3(C(=CCC4[C@@]3(C)CCC3[C@]4(C)CC[C@@H](C3(C)C)OC3OC[C@@H]([C@@H]([C@H]3O)O)O)[C@@H]2CC(CC1)(C)C)C)O)O
InChI InChI=1S/C53H86O23/c1-23-32(56)36(60)39(63)52(74-23,51(68)31(20-54)75-53(69,41(65)40(51)64)71-22-27-34(58)35(59)37(61)42(66)72-27)76-44(67)50-17-15-45(2,3)19-25(50)24-9-10-29-47(6)13-12-30(73-43-38(62)33(57)26(55)21-70-43)46(4,5)28(47)11-14-49(29,8)48(24,7)16-18-50/h9,23,25-43,54-66,68-69H,10-22H2,1-8H3/t23-,25+,26+,27?,28?,29?,30+,31?,32-,33+,34+,35?,36+,37+,38-,39+,40?,41+,42+,43?,47+,48-,49-,50+,51+,52?,53+/m1/s1
InChIKey LITJTAUOKFPJOC-OOKPMGQASA-N
Formula C53H86O23
HBA 23
HBD 15
MW 1091.25
Rotatable Bonds 9
TPSA 385.13
LogP -2.34
Number Rings 9
Number Aromatic Rings 0
Heavy Atom Count 76
Formal Charge 0
Fraction CSP3 0.94
Exact Mass 1090.56
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Dizygotheca kerchoveana Araliaceae Plantae —

Showing of synonyms

  • Melek FR, Miyase T, et al. (2004). Saponins and acylated saponins from Dizygotheca kerchoveana. Phytochemistry,2004,65(23),3089-3095. [View] [PubMed]
Pubchem: 162817442

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1COC(OC2)CCC2C3(CCCCO3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CC(CC8)OC9CCCCO9

Level: 4

Mol. Weight: 1091.25 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC6(CCCCO6)C7CCC(OC7)OCC8CCCCO8

Level: 3

Mol. Weight: 1091.25 g/mol

Structure

SMILES: C1OCCCC1C2(CCCCO2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC8CCCCO8

Level: 3

Mol. Weight: 1091.25 g/mol

Structure

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

Level: 2

Mol. Weight: 1091.25 g/mol

Structure

SMILES: C1OCCCC1C2(CCCCO2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CCCC7

Level: 2

Mol. Weight: 1091.25 g/mol

Structure

SMILES: O1CCCCC1COC(OC2)CCC2C3CCCCO3

Level: 2

Mol. Weight: 1091.25 g/mol

Structure

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

Level: 1

Mol. Weight: 1091.25 g/mol

Structure

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

Level: 1

Mol. Weight: 1091.25 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1091.25 g/mol

Structure

SMILES: C1OCCCC1C2CCCCO2

Level: 1

Mol. Weight: 1091.25 g/mol

Structure

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

Level: 0

Mol. Weight: 1091.25 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1091.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
288966.35
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
37765443.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.72
Plasma Protein Binding
67.36
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
Non-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
Non-Inhibitor

Excretion

Clearance
0.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-878327.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.69
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.05
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-68542462320.25
Rat (Acute)
3.62
Rat (Chronic Oral)
146.74
Fathead Minnow
86520291.23
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
7709120124.92
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-4277.27
Log(P)
0.27
Log S
-2.94
Log(Vapor Pressure)
-253857351.84
Melting Point
249.03
pKa Acid
-1849660.51
pKa Basic
-14864.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8591
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8591
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7862
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7862
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7258
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7258

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