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Muzigadial
- Family: Plantae - Canellaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | O=CC1=CC[C@@H]2[C@]([C@@]1(O)C=O)(C)CC[C@@H](C2=C)C |
|---|---|
| InChI | InChI=1S/C15H20O3/c1-10-6-7-14(3)13(11(10)2)5-4-12(8-16)15(14,18)9-17/h4,8-10,13,18H,2,5-7H2,1,3H3/t10-,13-,14-,15+/m0/s1 |
| InChIKey | LDAIOVKPAKFZHM-FBUXBERBSA-N |
| Formula | C15H20O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 248.32 |
| Rotatable Bonds | 2 |
| TPSA | 54.37 |
| LogP | 2.05 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 248.14 |
| 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 |
| 4 | Warburgia ugandensis | Canellaceae | Plantae | 549619 |
| 5 | Warburgia ugandensis | Canellaceae | Plantae | 549619 |
| 6 | Warburgia ugandensis and Warburgia stuhlmannii | Canellaceae | Plantae | 549618 |
Showing of synonyms
Muzigadial
Canellal
66550-09-2
(1S,4aS,6S,8aS)-1-hydroxy-6,8a-dimethyl-5-methylidene-4a,6,7,8-tetrahydro-4H-naphthalene-1,2-dicarbaldehyde
(1S,4aS,6S,8aS)-1-hydroxy-6,8a-dimethyl-5-methylene-4a,6,7,8-tetrahydro-4H-naphthalene-1,2-dicarbaldehyde
1,2-Naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-6,8a-dimethyl-5-methylene-, (1S-(1alpha,4aalpha,6beta,8abeta))-
C09626
AC1L9CN5
CHEBI:3355
DTXSID90985155
FM69728
Q27106040
(1alpha,4aalpha,6beta,8abeta)-(+-)-isomer of muzigadial
1-Hydroxy-6,8a-dimethyl-5-methylidene-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde
- 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]
- Olila D, Opuda-Asibo J, et al. (2001). Bioassay-guided studies on the cytotoxic and in vitro trypanocidal activities of a sesquiterpene (Muzigadial) derived from a Ugandan medicinal plant (Warburgia ugandensis). African Health Sciences,2001,1(1),13-15. [View] [PubMed]
- Taniguchi M, Kubo I. (1993). Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.. Journal of Natural Products,1993,56(9),1539-1546. [View] [PubMed]
- Rugutt JK, Ngigi AN, et al. (2006). Native Kenyan plants as possible alternatives to methyl bromide in soil fumigation. Phytomedicine,2006,13(8),576-583. [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: C=C1CCCC(C12)CC=CC2
Level: 0
Mol. Weight: 248.32 g/mol
Anti-plasmodial
Antibacterial
Antifungal
Antimicrobial
Antimycobacterial
Antitrypanosomal
Cytotoxic
Trypanocidal
Absorption
- Caco-2 (logPapp)
- -4.52
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.18
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.98
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- -0.01
- Plasma Protein Binding
- 41.77
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.31
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.62
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.41
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.53
- 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
- -0.85
- Rat (Acute)
- 3.9
- Rat (Chronic Oral)
- 1.11
- 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
- 316.73
- Hydration Free Energy
- -7.44
- Log(D) at pH=7.4
- 2.55
- Log(P)
- 3.16
- Log S
- -2.72
- Log(Vapor Pressure)
- -5.49
- Melting Point
- 111.89
- pKa Acid
- 5.47
- pKa Basic
- 4.7
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8396 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8396 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8345 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8345 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8333 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8333 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8226 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8226 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.8140 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.8140 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8028 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8028 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8000 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8000 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7778 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7778 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7760 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7760 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7718 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7718 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7675 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7675 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7579 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7579 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7408 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7408 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7376 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7376 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7331 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7331 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7318 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7318 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7230 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7230 |
| Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 3 | 0.7140 |
| Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 3 | 0.7140 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 2 | 0.7044 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 2 | 0.7044 |