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Cucurbitacin I 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/C(O)(C)C)(O)C)O)C)C(C2=O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C36H52O12/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/h9,11-13,18-19,21-22,25-28,30,37-38,41-43,45-46H,10,14-16H2,1-8H3/b12-11+/t18-,19-,21-,22+,25-,26+,27-,28+,30-,33+,34-,35+,36+/m1/s1 |
| InChIKey | LIIOJBIJVPGVGO-JZZAZZIQSA-N |
| Formula | C36H52O12 |
| HBA | 12 |
| HBD | 7 |
| MW | 676.8 |
| Rotatable Bonds | 7 |
| TPSA | 211.28 |
| LogP | 0.88 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 48 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 676.35 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Citrullus colocynthis | Cucurbitaceae | Plantae | 252529 |
Showing of synonyms
Cucurbitacin I 2-O-beta-D-glucopyranoside
Cucurbitacine I glucoside
29803-94-9
CHEBI:68917
(8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Cucurbitacine-I-glucoside
Beta-Glucoside de LA cucurbitacine (I)
Compound NP-002365
19-Nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione, 2-(beta-D-glucopyranosyloxy)-9-methyl-16,20,25-trihydroxy-
CHEMBL1765380
ACon1_002046
(10alpha,23E)-2-(beta-D-Glucopyranosyloxy)-16alpha,20,25-trihydroxy-9beta-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione
AKOS040735120
NCGC00179885-01
NCGC00179885-03
NS00094063
BRD-K10934705-001-01-9
Q27137272
(4R,9beta,16alpha,23E)-16,20,25-trihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-2-yl beta-D-glucopyranoside
Pubchem:
6441519
Cas:
29803-94-9
Zinc:
ZINC000067902915
Chebi:
68917
Nmrshiftdb2:
60066293
Metabolights:
MTBLC68917
Chembl:
CHEMBL1765380
No compound-protein relationship available.
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=C(C(=O)C4)OC5CCCCO5
Level: 1
Mol. Weight: 676.8 g/mol
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=CC(=O)C4
Level: 0
Mol. Weight: 676.8 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 676.8 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.02
- 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
- 30.33
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.780
- Plasma Protein Binding
- 106.53
- 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
- 3.390
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.880
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.800
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.480
- 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
- -56656.570
- Rat (Acute)
- 4.650
- Rat (Chronic Oral)
- 3.780
- Fathead Minnow
- 88.250
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 2275.330
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 2.450
- Log(P)
- 0.85
- Log S
- -3.12
- Log(Vapor Pressure)
- -65.41
- Melting Point
- 262.42
- pKa Acid
- 4.65
- pKa Basic
- 3.83
| 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 | 0.9263 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8424 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8226 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.8220 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8149 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8039 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7739 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7655 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7567 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7491 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7085 |