Canmetcon
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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:54:52 UTC
Update Date2019-01-11 19:50:54 UTC
HMDB IDHMDB0035873
Secondary Accession Numbers
  • HMDB35873
Metabolite Identification
Common NameMyristicin
DescriptionMyristicin 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
Structure
Data?1547236254
Synonyms
ValueSource
1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)- (9ci)HMDB
1-Allyl-3-methoxy-4,5-methylenedioxybenzeneHMDB
1-Methoxy-2,3-methylenedioxy-5-(2-propenyl)benzeneHMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxoleHMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole, 9ciHMDB
4-Methoxy-6-[2-propenyl]-1,3-benzodioxoleHMDB
5-Allyl-1-methoxy-2,3-(methylenedioxy)-benzeneHMDB
5-Allyl-1-methoxy-2,3-(methylenedioxy)benzeneHMDB
5-Allyl-2,3-(methylendioxy)anisoleHMDB
6-Allyl-4-methoxy-1,3-benzodioxoleHMDB
Myristicin (6ci)HMDB
Myristicin from parsley leaf oilHMDB
MyristicineHMDB
AsaricinMeSH
Chemical FormulaC11H12O3
Average Molecular Weight192.2112
Monoisotopic Molecular Weight192.07864425
IUPAC Name4-methoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
Traditional Namemyristicin
CAS Registry Number607-91-0
SMILES
COC1=CC(CC=C)=CC2=C1OCO2
InChI Identifier
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
InChI KeyBNWJOHGLIBDBOB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point< -20 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.83 g/LALOGPS
logP2.47ALOGPS
logP2.54ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.58 m³·mol⁻¹ChemAxon
Polarizability20.23 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-1900000000-f2a18c6e6e42ac39f661View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0api-2900000000-351fe6c26efba614a881View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-ac75cb6f6c3586da7aeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-b85689ec228e938e0eccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-5900000000-b81250e22454ed5d59d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-3477a22f9a26a9c1d389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-d7d0d133097da9fb4ec3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005i-4900000000-223806e9de1823c5a6e2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-371b2263b19500bf8f81View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014654
KNApSAcK IDC00002762
Chemspider ID4125
KEGG Compound IDC10480
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMyristicin
METLIN IDNot Available
PubChem Compound4276
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lee BK, Kim JH, Jung JW, Choi JW, Han ES, Lee SH, Ko KH, Ryu JH: Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells. Toxicol Lett. 2005 May 16;157(1):49-56. [PubMed:15795093 ]
  2. Morita T, Jinno K, Kawagishi H, Arimoto Y, Suganuma H, Inakuma T, Sugiyama K: Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/d-galactosamine-induced liver injury. J Agric Food Chem. 2003 Mar 12;51(6):1560-5. [PubMed:12617584 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .