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Daucovirgolide G
- Family: Plantae - Umbelliferae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpenoid
| Canonical Smiles | C/C=C(\C(=O)O[C@]1(C)C(=O)O[C@@H]2[C@@H]1[C@H](/C=C(\C)/CC/C=C(/C2)\C)OC(=O)[C@@]1(C)O[C@H]1C)/C |
|---|---|
| InChI | InChI=1S/C25H34O7/c1-8-16(4)21(26)32-25(7)20-18(29-22(27)24(6)17(5)31-24)12-14(2)10-9-11-15(3)13-19(20)30-23(25)28/h8,11-12,17-20H,9-10,13H2,1-7H3/b14-12+,15-11+,16-8-/t17-,18-,19-,20-,24-,25-/m0/s1 |
| InChIKey | MKEDSGMAAWRLGK-VOOWFMLGSA-N |
| Formula | C25H34O7 |
| HBA | 7 |
| HBD | 0 |
| MW | 446.54 |
| Rotatable Bonds | 4 |
| TPSA | 91.43 |
| LogP | 3.96 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.64 |
| Exact Mass | 446.23 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Daucus carota | Apiaceae | Plantae | 4039 |
| 2 | Daucus virgatus | Umbelliferae | Plantae | 1869349 |
| 3 | Daucus virgatus | Umbelliferae | Plantae | 1869349 |
Showing of synonyms
Daucovirgolide G
- Sirignano C, Snene A, et al. (2017). Angeloylated Germacranolides from Daucus virgatus and Their Plasmodium Transmission Blocking Activity. J Nat Prod,2017,80(10),2787-2794. [View] [PubMed]
- Sirignano C, Snene A, et al. (2019). Daucovirgolides I-L, four congeners of the antimalarial daucovirgolide G from Daucus virgatus. Fitoterapia,2019,137,104188. [View] [PubMed]
- Sirignano C, Hammami S, et al. (2021). Polyoxygenated germacranes from Daucus carota and their antimalarial transmission blocking activity. Phytochemistry, 2021, 183,112632.. [View] [PubMed]
No compound-protein relationship available.
SMILES: O1CC1C(=O)OC2C=CCCC=CCC(C23)OC(=O)C3
Level: 1
Mol. Weight: 446.54 g/mol
SMILES: C1C(=O)OC(C12)CC=CCCC=CC2
Level: 0
Mol. Weight: 446.54 g/mol
SMILES: C1CO1
Level: 0
Mol. Weight: 446.54 g/mol
Anti-plasmodial
Antimalarial
Absorption
- Caco-2 (logPapp)
- -5.01
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.67
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.32
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.53
- Plasma Protein Binding
- 49.09
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.5
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.97
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.58
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.07
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -55.01
- Rat (Acute)
- 2.87
- Rat (Chronic Oral)
- 1.92
- Fathead Minnow
- 4.84
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Toxic
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 393.99
- Hydration Free Energy
- -2.91
- Log(D) at pH=7.4
- 3.72
- Log(P)
- 4.98
- Log S
- -4.98
- Log(Vapor Pressure)
- -6.78
- Melting Point
- 82.18
- pKa Acid
- 6.88
- pKa Basic
- 2.2
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9141 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8140 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7915 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7643 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7315 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7269 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7243 |