Cucurbitacin L 2-O-beta-D-glucopyranoside - Compound Card

Cucurbitacin L 2-O-beta-D-glucopyranoside

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Cucurbitacin L 2-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles OCC1OC(OC2=C[C@@H]3C(=CC[C@@H]4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)C[C@H](C3C(C(=O)CCC(O)(C)C)(O)C)O)C)C(C2=O)(C)C)C(C(C1O)O)O
InChI InChI=1S/C36H54O12/c1-31(2,45)12-11-23(39)36(8,46)28-19(38)14-33(5)22-10-9-17-18(35(22,7)24(40)15-34(28,33)6)13-20(29(44)32(17,3)4)47-30-27(43)26(42)25(41)21(16-37)48-30/h9,13,18-19,21-22,25-28,30,37-38,41-43,45-46H,10-12,14-16H2,1-8H3/t18-,19-,21?,22+,25?,26?,27?,28?,30?,33+,34-,35+,36?/m1/s1
InChIKey QCAZYVAEXLGYLV-IQGGZGAMSA-N
Formula C36H54O12
HBA 12
HBD 7
MW 678.82
Rotatable Bonds 8
TPSA 211.28
LogP 1.1
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.81
Exact Mass 678.36
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Citrullus colocynthis Cucurbitaceae Plantae 252529

Showing of synonyms

  • Yoshikawa M, Morikawa T, et al. (2007). Bioactive Saponins and Glycosides. XXVII. 1) Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis. Chemical & pharmaceutical bulletin, 2007, 55(3), 428-34. [View] [PubMed]
Pubchem: 25203900

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=C(C(=O)C4)OC5CCCCO5

Level: 1

Mol. Weight: 678.82 g/mol

Structure

SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=CC(=O)C4

Level: 0

Mol. Weight: 678.82 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 678.82 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.92
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.08
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
30.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.77
Plasma Protein Binding
99.01
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.31
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.72
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.75
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-56652.52
Rat (Acute)
4.63
Rat (Chronic Oral)
3.74
Fathead Minnow
87.27
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
2505.51
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.32
Log(P)
1.17
Log S
-3.0
Log(Vapor Pressure)
-75.76
Melting Point
250.61
pKa Acid
4.13
pKa Basic
3.71
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 0.8434
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8429
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7890
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7762

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