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Cinnamolide-3beta-acetate
- Family: Plantae - Canellaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC=C1[C@@H]2COC1=O)C |
|---|---|
| InChI | InChI=1S/C17H24O4/c1-10(18)21-14-7-8-17(4)12-9-20-15(19)11(12)5-6-13(17)16(14,2)3/h5,12-14H,6-9H2,1-4H3/t12-,13-,14-,17+/m0/s1 |
| InChIKey | SHNYGCOMKCOSMW-AYMQEEERSA-N |
| Formula | C17H24O4 |
| HBA | 4 |
| HBD | 0 |
| MW | 292.38 |
| Rotatable Bonds | 1 |
| TPSA | 52.6 |
| LogP | 2.86 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.76 |
| Exact Mass | 292.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Warburgia ugandensis | Canellaceae | Plantae | 549619 |
| 2 | Warburgia ugandensis | Canellaceae | Plantae | 549619 |
| 3 | Warburgia ugandensis | Canellaceae | Plantae | 549619 |
Showing of synonyms
Cinnamolide-3beta-acetate
Cinnamolide-3.beta.-acetate
Cinnamolide-3beta-ol-acetate
3beta-Acetoxy-7-drimen-12,11-olide
[(5aR,7S,9aS,9bR)-6,6,9a-trimethyl-3-oxo-5,5a,7,8,9,9b-hexahydro-1H-benzo[e]isobenzofuran-7-yl] acetate
- Opiyo SA, Manguro LOA, et al. (2011). 7alpha-Acetylugandensolide and antimicrobial properties of Warburgia ugandensis extracts and isolates against sweet potato pathogens. Phytochemistry Letters,2011,4(2),161-165. [View] [PubMed]
- Wube AA, Bucar F, et al. (2010). Antiprotozoal activity of drimane and coloratane sesquiterpenes towards Trypanosoma brucei rhodesiense and Plasmodium falciparum in vitro. Phytotherapy Research,2010,24(10),1468-1472. [View] [PubMed]
- Wube AA, Bucar F, et al. (2005). Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. Phytochemistry,2005,66(19),2309-2315. [View] [PubMed]
No compound-protein relationship available.
SMILES: O=C1OCC(C1=2)C3C(CC2)CCCC3
Level: 0
Mol. Weight: 292.38 g/mol
Anti-plasmodial
Antitrypanosomal
Absorption
- Caco-2 (logPapp)
- -4.7
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.9
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.52
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.89
- Plasma Protein Binding
- 47.9
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- 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
- 12.22
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.62
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.2
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.45
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -1.26
- Rat (Acute)
- 2.07
- Rat (Chronic Oral)
- 1.66
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 355.26
- Hydration Free Energy
- -3.53
- Log(D) at pH=7.4
- 2.37
- Log(P)
- 2.64
- Log S
- -4.5
- Log(Vapor Pressure)
- -5.69
- Melting Point
- 133.8
- pKa Acid
- 9.43
- pKa Basic
- 6.4
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8901 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8901 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8574 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8574 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8265 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8265 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7285 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7285 |