3beta-hydroxylup-20(29)-en-28-oic acid 3-O-beta-D-glucuronopyranoside - Compound Card

3beta-hydroxylup-20(29)-en-28-oic acid 3-O-beta-D-glucuronopyranoside

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3beta-hydroxylup-20(29)-en-28-oic acid 3-O-beta-D-glucuronopyranoside

Structure
Zoomed Structure
  • Family: Araliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Lupane-Type Triterpene Glycoside
Canonical Smiles OC1C(O)C(OC(C1O)C(=O)O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)C(=O)O)C)C
InChI InChI=1S/C36H56O9/c1-18(2)19-10-15-36(31(42)43)17-16-34(6)20(24(19)36)8-9-22-33(5)13-12-23(32(3,4)21(33)11-14-35(22,34)7)44-30-27(39)25(37)26(38)28(45-30)29(40)41/h19-28,30,37-39H,1,8-17H2,2-7H3,(H,40,41)(H,42,43)/t19-,20+,21-,22+,23-,24+,25?,26?,27?,28?,30?,33-,34+,35+,36-/m0/s1
InChIKey SQYXYJWZICEBBS-ULMIPHOXSA-N
Formula C36H56O9
HBA 7
HBD 5
MW 632.84
Rotatable Bonds 5
TPSA 153.75
LogP 5.01
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 Schefflera actinophylla Araliaceae Plantae 52501

Showing of synonyms

  • Wanas AS, Matsunami K, et al. (2010). Triterpene glycosides and glucosyl esters, and a triterpene from the leaves of Schefflera actinophylla. Chemical and Pharmaceutical Bulletin,2010,58(12),1596-1601. [View] [PubMed]
Pubchem: 163034555

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCC(C5)OC6CCCCO6

Level: 1

Mol. Weight: 386.62 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 286.5 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.15
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
16.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.24
Plasma Protein Binding
102.41
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
1.71
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.3
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.54
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.09
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
-31748.55
Rat (Acute)
2.44
Rat (Chronic Oral)
3.69
Fathead Minnow
56.11
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
800.16
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.4
Log(P)
4.69
Log S
-4.6
Log(Vapor Pressure)
-20.72
Melting Point
260.24
pKa Acid
3.01
pKa Basic
8.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mexicain P84346 MEX1_JACME Jacaratia mexicana 3 0.8783
Mexicain P84346 MEX1_JACME Jacaratia mexicana 3 0.8783
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7833
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7833
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7723
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7723
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7629
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7629

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