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Colocynthoside A
- Family: Plantae - Cucurbitaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | OC[C@H]1O[C@@H](OC2=C[C@@H]3C(=C[C@@H]([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(OC(=O)C)(C)C)(O)C)O)C)O)C(C2=O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C38H54O14/c1-17(40)52-33(2,3)11-10-24(43)38(9,49)30-21(42)14-35(6)29-20(41)12-18-19(37(29,8)25(44)15-36(30,35)7)13-22(31(48)34(18,4)5)50-32-28(47)27(46)26(45)23(16-39)51-32/h10-13,19-21,23,26-30,32,39,41-42,45-47,49H,14-16H2,1-9H3/b11-10+/t19-,20+,21-,23-,26-,27+,28-,29+,30+,32-,35+,36-,37-,38+/m1/s1 |
| InChIKey | VJTYFWONTVLZJR-NKYHUVJXSA-N |
| Formula | C38H54O14 |
| HBA | 14 |
| HBD | 7 |
| MW | 734.84 |
| Rotatable Bonds | 8 |
| TPSA | 237.58 |
| LogP | 0.42 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 52 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.74 |
| Exact Mass | 734.35 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Citrullus colocynthis | Cucurbitaceae | Plantae | 252529 |
Showing of synonyms
Colocynthoside A
903588-40-9
((E,6R)-6-((7S,8S,9S,10R,13R,14S,16R,17R)-7,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-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)phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl) acetate
[(E,6R)-6-[(7S,8S,9S,10R,13R,14S,16R,17R)-7,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-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]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
CHEMBL4203865
AKOS040734121
Pubchem:
16216752
Cas:
903588-40-9
Zinc:
ZINC000255273118
Nmrshiftdb2:
70002371
Chembl:
CHEMBL4203865
No compound-protein relationship available.
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=C(C(=O)C4)OC5CCCCO5
Level: 1
Mol. Weight: 734.84 g/mol
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=CC(=O)C4
Level: 0
Mol. Weight: 734.84 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 734.84 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.17
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.310
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 170.18
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.680
- Plasma Protein Binding
- 102.26
- 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
- 4.350
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.470
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.870
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.220
- 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
- -309970.760
- Rat (Acute)
- 4.500
- Rat (Chronic Oral)
- 4.030
- Fathead Minnow
- 404.830
- 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
- 29927.180
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 2.110
- Log(P)
- 0.41
- Log S
- -2.88
- Log(Vapor Pressure)
- -959.63
- Melting Point
- 251.84
- pKa Acid
- 3.5
- pKa Basic
- 3.45
| 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 | 0.8340 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8302 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7789 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7605 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7535 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7502 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7479 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7197 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7129 |