Cucurbitacin B 2-O-beta-D-glucopyranosyl - Compound Card

Cucurbitacin B 2-O-beta-D-glucopyranosyl

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Cucurbitacin B 2-O-beta-D-glucopyranosyl

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CC(=O)OC(/C=C/C(=O)[C@@]([C@H]1[C@H](O)C[C@@]2(C1(C)CC(=O)[C@@]1(C2CC=C2[C@H]1CC(O)C(=O)C2(C)C)C)C)(O)C)(C)C
InChI InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20?,21-,22?,25+,29+,30?,31+,32+/m1/s1
InChIKey IXQKXEUSCPEQRD-KMYKGWGESA-N
Formula C32H46O8
HBA 8
HBD 3
MW 558.71
Rotatable Bonds 5
TPSA 138.2
LogP 3.5
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 558.32
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Bryonia cretica Cucurbitaceae Plantae 61884

Showing of synonyms

  • Matsuda H, Nakashima S, et al. (2010). Cucurbitane-Type Triterpenes with Anti-proliferative Effects on U937 Cells from an Egyptian Natural Medicine, Bryonia cretica: Structures of New Triterpene Glycosides, Bryoniaosides A and B. Chemical & pharmaceutical bulletin, 2010, 58(5), 747-51. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCC(=O)C4

Level: 0

Mol. Weight: 558.71 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
99.33
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
6.61
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.99
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.05
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.88
Micronucleos
Toxic
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
Toxic
T. Pyriformis
-1028.69
Rat (Acute)
4.43
Rat (Chronic Oral)
2.14
Fathead Minnow
5.33
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
474.26
Hydration Free Energy
-2.85
Log(D) at pH=7.4
3.31
Log(P)
3.18
Log S
-4.8
Log(Vapor Pressure)
-8.98
Melting Point
217.28
pKa Acid
6.69
pKa Basic
2.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8508
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8327
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7790
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7669
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7459
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7171
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7013

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