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

Cucurbitacin E 2-O-beta-D-glucopyranoside

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Cucurbitacin E 2-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles OCC1OC(OC2=CC3C4(C)C(=O)CC5(C(C4CC=C3C(C2=O)(C)C)(C)CC(C5C(C(=O)/C=C/C(OC(=O)C)(C)C)(O)C)O)C)C(C(C1O)O)O
InChI InChI=1S/C38H54O13/c1-18(40)51-33(2,3)13-12-25(42)38(9,48)30-21(41)15-35(6)24-11-10-19-20(37(24,8)26(43)16-36(30,35)7)14-22(31(47)34(19,4)5)49-32-29(46)28(45)27(44)23(17-39)50-32/h10,12-14,20-21,23-24,27-30,32,39,41,44-46,48H,11,15-17H2,1-9H3/b13-12+
InChIKey QKEJRKXVLGOJMB-OUKQBFOZSA-N
Formula C38H54O13
HBA 13
HBD 6
MW 718.84
Rotatable Bonds 8
TPSA 217.35
LogP 1.45
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 51
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 718.36
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: 5901827
Chebi: 186118
Nmrshiftdb2: 70002373

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 718.84 g/mol

Structure

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

Level: 0

Mol. Weight: 718.84 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 718.84 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.52
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
118.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.79
Plasma Protein Binding
23.76
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
4.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.81
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.26
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
-216774.36
Rat (Acute)
4.59
Rat (Chronic Oral)
3.8
Fathead Minnow
288.4
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
19677.95
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.54
Log(P)
1.38
Log S
-3.37
Log(Vapor Pressure)
-657.11
Melting Point
239.33
pKa Acid
4.26
pKa Basic
3.54
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 0.8426
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8299
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7101
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7095

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