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Cucurbitacin L-2-O-beta-glucoside
- Family: Plantae - Cucurbitaceae
- Kingdom: Plantae
-
Class: Saponin
- Subclass: Triterpenoid Saponin
| Canonical Smiles | OC[C@H]1OC(OC2=C[C@@H]3C(=CC[C@@H]4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)C[C@H](C3C(O)(C)C)O)C)C(C2=O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C31H46O10/c1-27(2)14-8-9-19-29(5)11-16(33)24(28(3,4)39)30(29,6)12-20(34)31(19,7)15(14)10-17(25(27)38)40-26-23(37)22(36)21(35)18(13-32)41-26/h8,10,15-16,18-19,21-24,26,32-33,35-37,39H,9,11-13H2,1-7H3/t15-,16-,18-,19+,21-,22+,23-,24?,26?,29+,30-,31+/m1/s1 |
| InChIKey | VSFNGKMYLNHFKF-UTIZKUFRSA-N |
| Formula | C31H46O10 |
| HBA | 10 |
| HBD | 6 |
| MW | 578.7 |
| Rotatable Bonds | 4 |
| TPSA | 173.98 |
| LogP | 1.0 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.81 |
| Exact Mass | 578.31 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Citrullus lanatus | Cucurbitaceae | Plantae | 3654 |
Showing of synonyms
Cucurbitacin L-2-O-beta-glucoside
- Abdelwahab SI, Hassan LE, et al. (2012). Cucurbitacin L 2-O-β-Glucoside Demonstrates Apoptogenesis in Colon Adenocarcinoma Cells (HT-29): Involvement of Reactive Oxygen and Nitrogen Species Regulation.. Evidence-based complementary and alternative medicine : eCAM,2012, 2012(), 490136. [View] [PubMed]
No compound-protein relationship available.
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=C(C(=O)C4)OC5CCCCO5
Level: 1
Mol. Weight: 578.7 g/mol
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=CC(=O)C4
Level: 0
Mol. Weight: 578.7 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 578.7 g/mol
Apoptogenesis in colonadenocarcinoma cells (ht-29)
Absorption
- Caco-2 (logPapp)
- -5.84
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.94
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 1.02
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.91
- Plasma Protein Binding
- 97.71
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 1.94
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.71
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.54
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.01
- 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
- -2741.85
- Rat (Acute)
- 4.14
- Rat (Chronic Oral)
- 3.25
- Fathead Minnow
- 7.27
- 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
- 480.69
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 2.37
- Log(P)
- 0.52
- Log S
- -2.95
- Log(Vapor Pressure)
- -11.28
- Melting Point
- 252.15
- pKa Acid
- 4.97
- pKa Basic
- 5.56
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8589 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 3 | 0.8274 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8061 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7875 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7406 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7257 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7245 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7015 |