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Cinnamolide
- Family: Plantae - Canellaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | O=C1OC[C@H]2C1=CC[C@@H]1[C@]2(C)CCCC1(C)C |
|---|---|
| InChI | InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)11-9-17-13(16)10(11)5-6-12(14)15/h5,11-12H,4,6-9H2,1-3H3/t11-,12-,15+/m0/s1 |
| InChIKey | UMUMRNRVJNFLPT-SLEUVZQESA-N |
| Formula | C15H22O2 |
| HBA | 2 |
| HBD | 0 |
| MW | 234.34 |
| Rotatable Bonds | 0 |
| TPSA | 26.3 |
| LogP | 3.32 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 234.16 |
| 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
(-)-Cinnamolide
23599-47-5
(5aS,9aS,9bR)-6,6,9a-trimethyl-5,5a,7,8,9,9b-hexahydro-1H-benzo[e][2]benzofuran-3-one
Naphtho(1,2-c)furan-3(1H)-one, 5,5a,6,7,8,9,9a,9b-octahydro-6,6,9a-trimethyl-, (5aS-(5a-alpha,9a-beta,9b-alpha))-
(5aS,9aS,9bR)-6,6,9a-trimethyl-5,5a,7,8,9,9b-hexahydro-1H-benzo(e)(2)benzofuran-3-one
CHEMBL218666
CHEBI:202004
DTXSID201339979
BDBM50465349
AKOS040762611
CS-0203775
(5aS,9aS,9bR)-6,6,9a-trimethyl-5,5a,7,8,9,9b-hexahydro-1H-benzo[e][2]benzouran-3-one
(5aS,9aS,9bR)-6,6,9a-trimethyl-5,5a,7,8,9,9b-hexahydro-1H-benzo[e]isobenzofuran-3-one
- 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]
CPRiL:
415144
SMILES: O=C1OCC(C1=2)C3C(CC2)CCCC3
Level: 0
Mol. Weight: 234.34 g/mol
Anti-plasmodial
Antibacterial
Antifungal
Antitrypanosomal
Absorption
- Caco-2 (logPapp)
- -4.77
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.67
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.65
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.93
- Plasma Protein Binding
- 46.26
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.9
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.15
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.18
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.42
- 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
- 1.56
- Rat (Acute)
- 1.8
- Rat (Chronic Oral)
- 1.39
- 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
- 329.13
- Hydration Free Energy
- -3.13
- Log(D) at pH=7.4
- 3.32
- Log(P)
- 3.24
- Log S
- -4.73
- Log(Vapor Pressure)
- -3.96
- Melting Point
- 104.77
- pKa Acid
- 9.62
- pKa Basic
- 7.04
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8185 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8185 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7994 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7994 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7836 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7836 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7721 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7721 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7601 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7601 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7490 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7490 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7403 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7403 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7203 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7203 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7127 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7127 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7101 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7101 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7021 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7021 |