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Oleanolic acid-3-O-beta-D-glucuronopyranoside
- Family: Plantae - Chenopodiaceae
- Kingdom: Plantae
-
Class: Saponin
- Subclass: Monodesmosidic Saponin
| Canonical Smiles | O[C@@H]1[C@@H](O)[C@@H](O[C@@H]([C@H]1O)C(=O)O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C |
|---|---|
| InChI | InChI=1S/C36H56O9/c1-31(2)14-16-36(30(42)43)17-15-34(6)19(20(36)18-31)8-9-22-33(5)12-11-23(32(3,4)21(33)10-13-35(22,34)7)44-29-26(39)24(37)25(38)27(45-29)28(40)41/h8,20-27,29,37-39H,9-18H2,1-7H3,(H,40,41)(H,42,43)/t20-,21-,22+,23-,24-,25-,26+,27-,29+,33-,34+,35+,36-/m0/s1 |
| InChIKey | IUCHKMAZAWJNBJ-RCYXVVTDSA-N |
| Formula | C36H56O9 |
| HBA | 7 |
| HBD | 5 |
| MW | 632.84 |
| Rotatable Bonds | 4 |
| TPSA | 153.75 |
| LogP | 5.15 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 45 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.89 |
| Exact Mass | 632.39 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Atriplex nummularia | Chenopodiaceae | Plantae | 3553 |
Showing of synonyms
Oleanolic acid-3-O-beta-D-glucuronopyranoside
Calenduloside E
26020-14-4
Silphioside F
Momordin Ib
Glycoside St-E
Oleanolic acid 3-O-glucuronide
3-O-(beta-D-Glucopyranuronosyl)oleanolic acid
UNII-184358RYCU
CHEBI:37658
184358RYCU
Oleanolic acid 3-O-beta-D-glucosiduronic acid
Oleanolic acid 3-O-beta-D-glucuronopyranoside
DTXSID90180668
28-DESGLUCOSYLCHIKUSETSUSAPONIN IVA
Olean-12-en-28-oic acid, 3beta-(beta-D-glucopyranuronosyloxy)-
28-hydroxy-28-oxoolean-12-en-3beta-yl beta-D-glucopyranosiduronic acid
Beta-D-Glucopyranosiduronic acid, (3beta)-17-carboxy-28-norolean-12-en-3-yl
Glucopyranosiduronic acid, 3beta-hydroxyolean-12-en-28-oic acid, beta-D-
DTXCID30103159
CalendulosideE
Oleanolic acid 3-O-monoglucuronide
(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
108322-31-2
B-D-Glucopyranosiduronic acid,(3b)-17-carboxy-28-norolean-12-en-3-yl
Oleanoic acid 3-O-glucuronide
Momordin B
CHEMBL446866
HY-N6850
AKOS030528265
FC74357
AC-34369
DA-62009
MS-30872
CS-0100275
C08964
Q27104421
3-O-(.BETA.-D-GLUCOPYRANURONOSYL)OLEANOLIC ACID
OLEANOLIC ACID 3-O-.BETA.-D-GLUCURONOPYRANOSIDE
.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.)-17-CARBOXY-28-NOROLEAN-12-EN-3-YL
GLUCOPYRANOSIDURONIC ACID, 3.BETA.-HYDROXYOLEAN-12-EN-28-OIC ACID, .BETA.-D-
OLEAN-12-EN-28-OIC ACID, 3.BETA.-(.BETA.-D-GLUCOPYRANURONOSYLOXY)-
- Christensen SB, Omar AA (1985). Atriplex nummularia, a source for the two molluscicide saponins: Hederagenin-3-O-beta-D-glucuronopyranoside and calenduloside E. Journal of Natural Products,1985,48(1),161-161. [View]
Pubchem:
176079
Cas:
26020-14-4
Zinc:
ZINC000008234238
Kegg Ligand:
C08964
Chebi:
37658
Nmrshiftdb2:
60071890
Chembl:
CHEMBL446866
Comptox:
DTXSID90180668
CPRiL:
87139
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6
Level: 1
Mol. Weight: 632.84 g/mol
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5
Level: 0
Mol. Weight: 632.84 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 632.84 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.93
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.12
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 11.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.17
- Plasma Protein Binding
- 106.13
- 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
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 0.83
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.54
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.49
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.03
- Micronucleos
- Safe
- 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
- -23169.79
- Rat (Acute)
- 2.37
- Rat (Chronic Oral)
- 3.67
- Fathead Minnow
- 44.38
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 501.35
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 2.4
- Log(P)
- 5.23
- Log S
- -4.67
- Log(Vapor Pressure)
- -14.44
- Melting Point
- 268.52
- pKa Acid
- 3.04
- pKa Basic
- 8.21
No predicted protein targets found for this compound.