Oleanolic acid-3-O-beta-glucopyranoside - Compound Card

Oleanolic acid-3-O-beta-glucopyranoside

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Oleanolic acid-3-O-beta-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Chenopodiaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Triterpenoid Saponin
Canonical Smiles OC[C@H]1O[C@@H](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)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C36H58O8/c1-31(2)14-16-36(30(41)42)17-15-34(6)20(21(36)18-31)8-9-24-33(5)12-11-25(32(3,4)23(33)10-13-35(24,34)7)44-29-28(40)27(39)26(38)22(19-37)43-29/h8,21-29,37-40H,9-19H2,1-7H3,(H,41,42)/t21-,22+,23-,24+,25-,26+,27-,28+,29-,33-,34+,35+,36-/m0/s1
InChIKey ZNFRITHWVZXJRK-YHFBEQRYSA-N
Formula C36H58O8
HBA 7
HBD 5
MW 618.85
Rotatable Bonds 4
TPSA 136.68
LogP 5.06
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.92
Exact Mass 618.41
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Bassia muricata Chenopodiaceae Plantae 267505

Showing of synonyms

  • Kamel MS, Mohamed KM, et al. (2001). Acylated flavonoid glycosides from Bassia muricata. Phytochemistry,2001,57(8),1259-1262. [View] [PubMed]
Pubchem: 9986341
Chebi: 182952
Nmrshiftdb2: 60058741
Bindingdb: 50235147

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 618.85 g/mol

Structure

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

Level: 0

Mol. Weight: 618.85 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 618.85 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.020
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
8.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.180
Plasma Protein Binding
107.92
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
1.750
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.380
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.070
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
-16503.730
Rat (Acute)
2.690
Rat (Chronic Oral)
3.380
Fathead Minnow
35.100
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
431.880
Hydration Free Energy
-2.920
Log(D) at pH=7.4
4.030
Log(P)
5.1
Log S
-4.92
Log(Vapor Pressure)
-14.71
Melting Point
257.69
pKa Acid
4.62
pKa Basic
7.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8081
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8081
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7912
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7912
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7723
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7723

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