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Cucurbitacin J 2-O-beta-D-glucopyranoside
- Family: Plantae - Cucurbitaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | OC[C@H]1O[C@@H](OC2=C[C@@H]3C(=CC[C@@H]4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)C[C@H]([C@@H]3[C@](C(=O)C[C@H](C(O)(C)C)O)(O)C)O)C)C(C2=O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C36H54O13/c1-31(2)16-9-10-21-33(5)13-18(38)28(36(8,47)23(40)12-22(39)32(3,4)46)34(33,6)14-24(41)35(21,7)17(16)11-19(29(31)45)48-30-27(44)26(43)25(42)20(15-37)49-30/h9,11,17-18,20-22,25-28,30,37-39,42-44,46-47H,10,12-15H2,1-8H3/t17-,18-,20-,21+,22-,25-,26+,27-,28+,30-,33+,34-,35+,36+/m1/s1 |
| InChIKey | XPEAYHKXEWXAKV-WOVCZDRSSA-N |
| Formula | C36H54O13 |
| HBA | 13 |
| HBD | 8 |
| MW | 694.82 |
| Rotatable Bonds | 8 |
| TPSA | 231.51 |
| LogP | 0.07 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 49 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.81 |
| Exact Mass | 694.36 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Citrullus colocynthis | Cucurbitaceae | Plantae | 252529 |
Showing of synonyms
Cucurbitacin J 2-O-beta-D-glucopyranoside
CHEBI:68913
(8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R,5R)-2,5,6-trihydroxy-6-methyl-3-oxoheptan-2-yl]-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
(4R,9beta,16alpha,24R)-16,20,24,25-tetrahydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5-dien-2-yl beta-D-glucopyranoside
(8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-4,4,9,13,14-pentamethyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-17-((2R,5R)-2,5,6-trihydroxy-6-methyl-3-oxoheptan-2-yl)-8,10,12,15,16,17-hexahydro-7H-cyclopenta(a)phenanthrene-3,11-dione
CHEMBL1923786
Q27137268
Pubchem:
6324996
Zinc:
ZINC000082139780
Chebi:
68913
Nmrshiftdb2:
70002370
Metabolights:
MTBLC68913
Chembl:
CHEMBL1923786
No compound-protein relationship available.
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=C(C(=O)C4)OC5CCCCO5
Level: 1
Mol. Weight: 694.82 g/mol
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=CC(=O)C4
Level: 0
Mol. Weight: 694.82 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 694.82 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.23
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.060
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 47.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.820
- Plasma Protein Binding
- 103.72
- 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
- 2.040
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -4.570
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.790
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.620
- 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
- -86078.920
- Rat (Acute)
- 4.350
- Rat (Chronic Oral)
- 3.790
- Fathead Minnow
- 123.220
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 5289.410
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 2.390
- Log(P)
- 0.16
- Log S
- -2.63
- Log(Vapor Pressure)
- -155.03
- Melting Point
- 266.31
- pKa Acid
- 3.77
- pKa Basic
- 5.46
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8930 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8836 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8306 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8299 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.8012 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7930 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7610 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7360 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7231 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7107 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7093 |