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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:54:52 UTC
Update Date2022-03-07 02:54:40 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?1563862785
Synonyms
ValueSource
5-Allyl-1-methoxy-2,3-(methylenedioxy)benzeneMeSH
AsaricinMeSH
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-2,3-(methylendioxy)anisoleHMDB
6-Allyl-4-methoxy-1,3-benzodioxoleHMDB
Myristicin (6ci)HMDB
Myristicin from parsley leaf oilHMDB
MyristicineHMDB
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
Description 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
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< -20 °CNot Available
Boiling Point171.00 to 173.00 °C. @ 40.00 mm HgThe Good Scents Company Information System
Water Solubility46.43 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.586 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker144.74130932474
[M+H]+Baker141.69130932474
[M-H]-Not Available144.741http://allccs.zhulab.cn/database/detail?ID=AllCCS00001794
[M+H]+Not Available141.691http://allccs.zhulab.cn/database/detail?ID=AllCCS00001794
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.71431661259
DarkChem[M-H]-141.48231661259
DeepCCS[M+H]+136.62630932474
DeepCCS[M-H]-132.79830932474
DeepCCS[M-2H]-170.3930932474
DeepCCS[M+Na]+145.92930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MyristicinCOC1=CC(CC=C)=CC2=C1OCO22231.0Standard polar33892256
MyristicinCOC1=CC(CC=C)=CC2=C1OCO21493.1Standard non polar33892256
MyristicinCOC1=CC(CC=C)=CC2=C1OCO21511.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Myristicin GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-1900000000-f2a18c6e6e42ac39f6612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Myristicin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-371b2263b19500bf8f812014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Myristicin , positive-QTOFsplash10-0api-2900000000-351fe6c26efba614a8812017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 10V, Positive-QTOFsplash10-0006-0900000000-ac75cb6f6c3586da7aea2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 20V, Positive-QTOFsplash10-0006-1900000000-b85689ec228e938e0ecc2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 40V, Positive-QTOFsplash10-00lu-5900000000-b81250e22454ed5d59d32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 10V, Negative-QTOFsplash10-0006-0900000000-3477a22f9a26a9c1d3892015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 20V, Negative-QTOFsplash10-0006-0900000000-d7d0d133097da9fb4ec32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 40V, Negative-QTOFsplash10-005i-4900000000-223806e9de1823c5a6e22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 10V, Positive-QTOFsplash10-0006-0900000000-f50d22f4768250e3bdf72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 20V, Positive-QTOFsplash10-0006-0900000000-eccd8c2af56eaae25cc62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 40V, Positive-QTOFsplash10-03fu-9300000000-7be3c7d384d05c36876b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 10V, Negative-QTOFsplash10-0006-0900000000-3b8fc77e2c5dffca77652021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 20V, Negative-QTOFsplash10-0006-0900000000-bdb133e54a9aea38147a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Myristicin 40V, Negative-QTOFsplash10-01p9-7900000000-cea14d0b0dcb3a57c3522021-09-25Wishart LabView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1104961
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.. .