3-O-[O-beta-d-glucopyranosyl(1→3)-beta-d-glucopyranosyl] oleanolic acid - Compound Card

3-O-[O-beta-d-glucopyranosyl(1→3)-beta-d-glucopyranosyl] oleanolic acid

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3-O-[O-beta-d-glucopyranosyl(1→3)-beta-d-glucopyranosyl] oleanolic acid

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Triterpenoid Saponin
Canonical Smiles OCC1OC(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(C(C1O)OC1OC(CO)C(C(C1O)O)O)O
InChI InChI=1S/C42H68O13/c1-37(2)14-16-42(36(50)51)17-15-40(6)21(22(42)18-37)8-9-26-39(5)12-11-27(38(3,4)25(39)10-13-41(26,40)7)54-35-32(49)33(29(46)24(20-44)53-35)55-34-31(48)30(47)28(45)23(19-43)52-34/h8,22-35,43-49H,9-20H2,1-7H3,(H,50,51)/t22-,23?,24?,25-,26+,27-,28?,29?,30?,31?,32?,33?,34?,35?,39-,40+,41+,42-/m0/s1
InChIKey KZIQZLSHACGNHX-JLRAIIHGSA-N
Formula C42H68O13
HBA 12
HBD 8
MW 780.99
Rotatable Bonds 7
TPSA 215.83
LogP 2.88
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 55
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 780.47
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Catunaregam nilotica Rubiaceae Plantae 353862

Showing of synonyms

  • Lemmich E, Cornett C, et al. (1995). Molluscicidal saponins from Catunaregam nilotica. Phytochemistry, 1995, 39(1), 63-8. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 780.99 g/mol

Structure

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

Level: 1

Mol. Weight: 780.99 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 780.99 g/mol

Structure

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

Level: 0

Mol. Weight: 780.99 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 780.99 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
8.17
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1875.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.01
Plasma Protein Binding
83.15
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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
1.76
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-46.75
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.23
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
8.36
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
-3402647.78
Rat (Acute)
3.08
Rat (Chronic Oral)
3.94
Fathead Minnow
4301.0
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
379420.48
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.69
Log(P)
4.1
Log S
-3.13
Log(Vapor Pressure)
-12393.17
Melting Point
247.62
pKa Acid
-50.24
pKa Basic
8.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8023

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