2alpha,3beta,6beta,19alpha-tetrahydroxyoleanolic acid 28-O-beta-D-glucopyranoside - Compound Card

2alpha,3beta,6beta,19alpha-tetrahydroxyoleanolic acid 28-O-beta-D-glucopyranoside

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2alpha,3beta,6beta,19alpha-tetrahydroxyoleanolic acid 28-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Combretaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Pentacyclic Triterpenoid
Canonical Smiles OC[C@H]1O[C@@H](OC(=O)[C@@]23CCC([C@H]([C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)C[C@@H](O)[C@@H]2[C@]4(C)C[C@H]([C@@H](C2)O)O)O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C34H54O11/c1-30(2)8-10-34(29(43)45-28-26(41)25(40)24(39)21(15-35)44-28)11-9-32(4)16(23(34)27(30)42)6-7-22-31(3)13-20(38)18(36)12-17(31)19(37)14-33(22,32)5/h6,17-28,35-42H,7-15H2,1-5H3/t17-,18-,19-,20-,21-,22-,23-,24-,25+,26-,27+,28+,31+,32-,33-,34+/m1/s1
InChIKey QAVCHNYMJQRDMK-AVVMLROQSA-N
Formula C34H54O11
HBA 11
HBD 8
MW 638.8
Rotatable Bonds 3
TPSA 197.37
LogP 0.77
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 45
Formal Charge 0
Fraction CSP3 0.91
Exact Mass 638.37
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Combretum hartmannianum Combretaceae Plantae 99434

Showing of synonyms

  • Morgan AMA, Mohamed AE, et al. (2018). Pentacyclic triterpenes from the stem bark of Combretum hartmannianum Schweinf. Biochemical Systematics and Ecology, 2018, 77, 48-50. [View]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 638.8 g/mol

Structure

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

Level: 0

Mol. Weight: 638.8 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 638.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.050
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
14.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.740
Plasma Protein Binding
91.37
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
Non-Inhibitor

Excretion

Clearance
0.360
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-5.340
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.140
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
4.420
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
-27054.810
Rat (Acute)
4.430
Rat (Chronic Oral)
3.340
Fathead Minnow
49.050
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
639.070
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.890
Log(P)
1.42
Log S
-2.52
Log(Vapor Pressure)
-15.78
Melting Point
245.69
pKa Acid
5.83
pKa Basic
6.0
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 0.7755
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7326
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7246

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