Myristicin
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Basic Info
| Common Name | Myristicin(F04817) |
| 2D Structure | |
| Description | Myristicin is found in anise. Myristicin is a constituent of dill, nutmeg, parsley and many other essential oils. May be responsible for psychotic effects of nutmeg at large doses Myristicin, 3-methoxy,4,5-methylendioxy-allylbenzene, is a natural organic compound present in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill. Myristicin is a naturally occurring insecticide and acaricide with possible neurotoxic effects on dopaminergic neurons[citation needed]. It has hallucinogenic properties at doses much higher than used in cooking. Myristicin is a weak inhibitor of monoamine oxidase. Myristicin has been shown to exhibit apoptotic and hepatoprotective functions (A7836, A7837). Myristicin belongs to the family of Benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. |
| FRCD ID | F04817 |
| CAS Number | 607-91-0 |
| PubChem CID | 4276 |
| Formula | C11H12O3 |
| IUPAC Name | 4-methoxy-6-prop-2-enyl-1,3-benzodioxole |
| InChI Key | BNWJOHGLIBDBOB-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3,5-6H,1,4,7H2,2H3 |
| Canonical SMILES | COC1=CC(=CC2=C1OCO2)CC=C |
| Isomeric SMILES | COC1=CC(=CC2=C1OCO2)CC=C |
| Wikipedia | Myristicin |
| Synonyms |
6-Allyl-4-methoxy-1,3-benzodioxole
Myristicin
607-91-0
Myristicin (6CI)
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole
Myristicine
5-Allyl-1-methoxy-2,3-(methylenedioxy)benzene
UNII-04PD6CT78W
1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)-
CCRIS 6782
|
| Classifies |
Plant Toxin
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Benzodioxoles |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzodioxoles |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Benzodioxole - Anisole - Alkyl aryl ether - Benzenoid - Oxacycle - Ether - Acetal - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 192.214 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 205 |
| Monoisotopic Mass | 192.079 |
| Exact Mass | 192.079 |
| XLogP | 2.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9504 |
| Human Intestinal Absorption | HIA+ | 0.9941 |
| Caco-2 Permeability | Caco2+ | 0.7041 |
| P-glycoprotein Substrate | Non-substrate | 0.6339 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5534 |
| Inhibitor | 0.5238 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7919 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6495 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8457 |
| CYP450 2D6 Substrate | Non-substrate | 0.8541 |
| CYP450 3A4 Substrate | Non-substrate | 0.6280 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7550 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5081 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.6549 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7941 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7960 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8977 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9172 |
| Non-inhibitor | 0.9680 | |
| AMES Toxicity | Non AMES toxic | 0.8921 |
| Carcinogens | Non-carcinogens | 0.9263 |
| Fish Toxicity | High FHMT | 0.9280 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9919 |
| Honey Bee Toxicity | High HBT | 0.8361 |
| Biodegradation | Not ready biodegradable | 0.6031 |
| Acute Oral Toxicity | III | 0.7825 |
| Carcinogenicity (Three-class) | Warning | 0.4781 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.5156 | LogS |
| Caco-2 Permeability | 1.2767 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.6850 | LD50, mol/kg |
| Fish Toxicity | 0.2935 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6425 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Identification of highly effective antitrypanosomal compounds in essential oilsfrom the Apiaceae family. | Ecotoxicol Environ Saf | 2018 Jul 30 | 29549739 |
| Efficacy of the Volatile Oil from Water Celery (Helosciadium nodiflorum, Apiaceae) against the Filariasis Vector Culex quinquefasciatus, the Housefly Musca domestica, and the African Cotton Leafworm Spodoptera littoralis. | Chem Biodivers | 2017 Dec | 28862791 |
| Antifungal and antibacterial activities of Petroselinum crispum essential oil. | Genet Mol Res | 2016 Jul 29 | 27525894 |
| Chemical composition and antibiofilm activity of Petroselinum crispum and Ocimum basilicum essential oils against Vibrio spp. strains. | Microb Pathog | 2016 Jan | 26596707 |
| Structure-Activity Relationships for DNA Damage by Alkenylbenzenes in Turkey Egg Fetal Liver. | Toxicol Sci | 2016 Apr | 26719370 |
| A straightforward method to determine flavouring substances in food by GC-MS. | Food Chem | 2015 May 1 | 25529699 |
| Analysis of the essential oil of Illicium henryi Diels root bark and itsinsecticidal activity against Liposcelis bostrychophila Badonnel. | J Food Prot | 2015 Apr | 25836404 |
| Nutmeg poisonings: a retrospective review of 10 years experience from the Illinois Poison Center, 2001-2011. | J Med Toxicol | 2014 Jun | 24452991 |
| Quantitation of tr-cinnamaldehyde, safrole and myristicin in cola-flavoured soft drinks to improve the assessment of their dietary exposure. | Food Chem Toxicol | 2013 Sep | 23845511 |
| Cytotoxic activity of essential oils of aerial parts and ripe fruits of Echinophora spinosa (Apiaceae). | Nat Prod Commun | 2013 Nov | 24427963 |
| Predicting the hepatocarcinogenic potential of alkenylbenzene flavoring agentsusing toxicogenomics and machine learning. | Toxicol Appl Pharmacol | 2010 Mar 15 | 20004213 |
| Chemical composition and in vitro evaluation of antioxidant and antibacterialactivities of the root oil of Ridolfia segetum (L.) Moris from Tunisia. | Nat Prod Res | 2010 Apr | 20397101 |
| Determination of alkenylbenzenes and related flavour compounds in food samples byon-column preconcentration-capillary liquid chromatography. | J Chromatogr A | 2009 Oct 23 | 19735919 |
| Distinguishing chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry. | J Agric Food Chem | 2009 Jul 8 | 19507874 |
| Quantification of flavor-related compounds in the unburned contents of bidi and clove cigarettes. | J Agric Food Chem | 2006 Nov 1 | 17061837 |
| Essential oil composition of Piper guineense and its antimicrobial activity.Another chemotype from Nigeria. | Phytother Res | 2005 Apr | 16041738 |
| Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/d-galactosamine-induced liver injury. | J Agric Food Chem | 2003 Mar 12 | 12617584 |
| Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre. | Forensic Sci Int | 2001 Apr 15 | 11343860 |
| Quantitation of flavor-related alkenylbenzenes in tobacco smoke particulate by selected ion monitoring gas chromatography-mass spectrometry. | J Agric Food Chem | 2000 Apr | 10775389 |
| Toxicological evaluation of myristicin. | Nat Toxins | 1997 | 9496377 |
Targets
- General Function:
- Serotonin binding
- Specific Function:
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
- Gene Name:
- MAOA
- Uniprot ID:
- P21397
- Molecular Weight:
- 59681.27 Da
- Mechanism of Action:
- Myristicin is a weak inhibitor of monoamine oxidase.
References
- Wikipedia. Myristicin. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Myristicin
- General Function:
- Primary amine oxidase activity
- Specific Function:
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
- Gene Name:
- MAOB
- Uniprot ID:
- P27338
- Molecular Weight:
- 58762.475 Da
- Mechanism of Action:
- Myristicin is a weak inhibitor of monoamine oxidase.
References
- Wikipedia. Myristicin. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Myristicin