3beta-hydroxyurs-12-en-28-oic acid 3-O-beta-D-glucuronopyranoside 6'-O-butyl ester - Compound Card

3beta-hydroxyurs-12-en-28-oic acid 3-O-beta-D-glucuronopyranoside 6'-O-butyl ester

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3beta-hydroxyurs-12-en-28-oic acid 3-O-beta-D-glucuronopyranoside 6'-O-butyl ester

Structure
Zoomed Structure
  • Family: Plantae - Araliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ursane-Type Triterpene Glycoside
Canonical Smiles CCCCOC(=O)C1OC(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]3[C@@H](C)[C@H](C)CC2)C(=O)O)C)C)C(C(C1O)O)O
InChI InChI=1S/C40H64O9/c1-9-10-21-47-33(44)32-30(42)29(41)31(43)34(49-32)48-27-15-16-37(6)25(36(27,4)5)14-17-39(8)26(37)12-11-24-28-23(3)22(2)13-18-40(28,35(45)46)20-19-38(24,39)7/h11,22-23,25-32,34,41-43H,9-10,12-21H2,1-8H3,(H,45,46)/t22-,23+,25+,26-,27+,28+,29?,30?,31?,32?,34?,37+,38-,39-,40+/m1/s1
InChIKey RAOVWTAEPDTVIJ-SCZRSGIJSA-N
Formula C40H64O9
HBA 8
HBD 4
MW 688.94
Rotatable Bonds 7
TPSA 142.75
LogP 6.26
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 49
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 688.46
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: 163057851

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 688.94 g/mol

Structure

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

Level: 0

Mol. Weight: 688.94 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 688.94 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.47
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
107.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.49
Plasma Protein Binding
108.58
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
4.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.17
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.35
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-198714.99
Rat (Acute)
2.54
Rat (Chronic Oral)
3.07
Fathead Minnow
262.9
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
18849.13
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.02
Log(P)
6.62
Log S
-5.12
Log(Vapor Pressure)
-588.05
Melting Point
217.07
pKa Acid
4.28
pKa Basic
7.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7988
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7988
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7900
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7900
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7470
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7470

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