NP-MRD: Showing NP-Card for Myristicin (NP0048364)

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Record Information

Version

2.0

Created at

2022-03-17 20:55:20 UTC

Updated at

2025-02-11 15:46:02 UTC

NP-MRD ID

NP0048364

Natural Product DOI

https://doi.org/10.57994/0472

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Myristicin

Description

Myristicin, also known as myristicin (6ci) or asaricin, 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. Myristicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Myristicin is a balsamic, spice, and warm tasting compound. Outside of the human body, Myristicin is found, on average, in the highest concentration within a few different foods, such as parsnips, parsley, and nutmegs and in a lower concentration in caraway, wild carrots, and carrots. Myristicin has also been detected, but not quantified in, several different foods, such as wild celeries, fennels, herbs and spices, dills, and anises. This could make myristicin a potential biomarker for the consumption of these foods. Myristicin is a potentially toxic compound. Myristicin is found in Asarum asperum, Asarum fauriei, Asarum heteropoides var.mandshuricum, Asarum lutchuense, Asarum sieboldii , Averrhoa carambola , Brucea javanica, Caesulia axillaris, Callistemon rigidus, Canella winterana, Cassia grandis, Chaerophyllum azoricum, Cinnamomum glanduliferum , Cinnamomum subavenium, Cinnamomum tenuifolium, Conioselinum vaginatum, Vincetoxicum hirundinaria, Degeneria vitiensis, Echinophora chrysantha, Echinophora tenuifolia, Alpinia speciosa , Ferula equisetacea, Ferula feruloides, Ferula rutbaensis, Illicium simonsii, Ligusticum jeholense, Ligusticum scoticum , Ligusticum sinense , Lindera neesiana , Macropiper excelsum, Magnolia salicifolia , Mosla cavaleriei, Nigella sativa L , Ocotea foetens, Oenanthe javanica, Orthodon spp., Peperomia bracteata, Perilla frutescens, Perilla frutescens var.acuta , Perilla frutescens var.crispa , Petroselimum crispum, Peucedanum zenkeri, Piper aduncum , Piper auritum, Piper guineense, Piper marginatum, Piper mullesua, Piper nigrum, Piper regnellii , Piper sanctum, Piper solmsianum, Sassafras albidum, Tasmannia lanceolata, Todaroa aurea and Zingiber officinale . Myristicin was first documented in 2003 (PMID: 12617584). Myristicin exerts possible neurotoxic effects on dopaminergic neurons and is a weak inhibitor of monoamine oxidase (PMID: 15795093) (PMID: 36762483).

Structure

MOL SDF PDB SMILES InChI

Myristicin
  Mrv1652309251702222D          

 14 15  0  0  0  0            999 V2000
    5.9797    0.0450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9797   -1.2826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1989   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1989   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4611   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3410   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 11  1  0  0  0  0
  2  6  1  0  0  0  0
  2 11  1  0  0  0  0
  3  7  1  0  0  0  0
  3 13  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 12  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048364

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
BNWJOHGLIBDBOB-UHFFFAOYSA-N

> <FORMULA>
C11H12O3

> <MOLECULAR_WEIGHT>
192.2112

> <EXACT_MASS>
192.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.230269076483445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.537378751

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.538876091827281

> <JCHEM_POLAR_SURFACE_AREA>
27.69

> <JCHEM_REFRACTIVITY>
52.575400000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
myristicin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 25-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Myristicin                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-SEP-17         0                                  
HETATM    1  O   UNK     0      11.162   0.084   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.162  -2.394   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.371   1.925   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.037  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.705  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.705  -1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.371   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.371  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.037  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.704  -2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.061  -1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.370  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.037   2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.036  -2.695   0.000  0.00  0.00           C+0
CONECT    1    5   11                                                       
CONECT    2    6   11                                                       
CONECT    3    7   13                                                       
CONECT    4    8    9   10                                                  
CONECT    5    1    6    7                                                  
CONECT    6    2    5    8                                                  
CONECT    7    3    5    9                                                  
CONECT    8    4    6                                                       
CONECT    9    4    7                                                       
CONECT   10    4   12                                                       
CONECT   11    1    2                                                       
CONECT   12   10   14                                                       
CONECT   13    3                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)- (9ci)	HMDB
1-Allyl-3-methoxy-4,5-methylenedioxybenzene	HMDB
1-Methoxy-2,3-methylenedioxy-5-(2-propenyl)benzene	HMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole	HMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole, 9ci	HMDB
4-Methoxy-6-[2-propenyl]-1,3-benzodioxole	HMDB
5-Allyl-1-methoxy-2,3-(methylenedioxy)-benzene	HMDB
5-Allyl-1-methoxy-2,3-(methylenedioxy)benzene	HMDB
5-Allyl-2,3-(methylendioxy)anisole	HMDB
6-Allyl-4-methoxy-1,3-benzodioxole	HMDB
Myristicin (6ci)	HMDB
Myristicin from parsley leaf oil	HMDB
Myristicine	HMDB
Asaricin	HMDB

Chemical Formula

C₁₁H₁₂O₃

Average Mass

192.2112 Da

Monoisotopic Mass

192.07864 Da

IUPAC Name

4-methoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole

Traditional Name

myristicin

CAS Registry Number

607-91-0

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 Key

BNWJOHGLIBDBOB-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.33, CDCl₃, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Asarum asperum	LOTUS Database	35616633
Asarum fauriei	LOTUS Database	35616633
Asarum heteropoides var.mandshuricum	Plant	KNApSAcK
Asarum lutchuense	LOTUS Database	35616633
Asarum sieboldii	Plant	KNApSAcK
Averrhoa carambola	Plant	KNApSAcK
Brucea javanica	LOTUS Database	35616633
Caesulia axillaris	LOTUS Database	35616633
Callistemon rigidus	LOTUS Database	35616633
Canella winterana	LOTUS Database	35616633
Carum carvi	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cassia grandis	LOTUS Database	35616633
Chaerophyllum azoricum	LOTUS Database	35616633
Cinnamomum glanduliferum	Plant	KNApSAcK
Cinnamomum subavenium	LOTUS Database	35616633
Cinnamomum tenuifolium	Plant	KNApSAcK
Conioselinum vaginatum	Plant	KNApSAcK
Coriandrum sativum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cynanchum vincetoxicum	LOTUS Database	35616633
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	12926889
Degeneria vitiensis	LOTUS Database	35616633
Echinophora chrysantha	LOTUS Database	35616633
Echinophora tenuifolia	LOTUS Database	35616633
Etlingera elatior	Plant	KNApSAcK
Ferula equisetacea	LOTUS Database	35616633
Ferula feruloides	LOTUS Database	35616633
Ferula rutbaensis	LOTUS Database	35616633
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Illicium simonsii	LOTUS Database	35616633
Levisticum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ligusticum jeholense	Plant	KNApSAcK
Ligusticum scoticum	Plant	KNApSAcK
Ligusticum sinense	Plant	KNApSAcK
Lindera neesiana	Plant	KNApSAcK
Macropiper excelsum	LOTUS Database	35616633
Magnolia salicifolia	Plant	KNApSAcK
Mosla cavaleriei	LOTUS Database	35616633
Myristica fragrans		Not Available
Myristica fragrans	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Nigella sativa L	Plant	KNApSAcK
Ocotea foetens	LOTUS Database	35616633
Oenanthe javanica	LOTUS Database	35616633
Orthodon spp.	Animalia	KNApSAcK
Pastinaca sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Peperomia bracteata	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Perilla frutescens var.acuta	Plant	KNApSAcK
Perilla frutescens var.crispa	Plant	KNApSAcK
Petroselimum crispum	-	KNApSAcK
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Peucedanum zenkeri	LOTUS Database	35616633
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper aduncum	Plant	KNApSAcK
Piper auritum	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Piper marginatum	LOTUS Database	35616633
Piper mullesua	LOTUS Database	35616633
Piper nigrum	LOTUS Database	35616633
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper regnellii	Plant	KNApSAcK
Piper sanctum	LOTUS Database	35616633
Piper solmsianum	Plant	KNApSAcK
Sassafras albidum	LOTUS Database	35616633
Tasmannia lanceolata	LOTUS Database	35616633
Todaroa aurea	LOTUS Database	35616633
Vaccinium corymbosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:68234 )
Monolignols (C10480 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.47	ALOGPS
logP	2.54	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.58 m³·mol⁻¹	ChemAxon
Polarizability	20.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035873

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Myristicin

METLIN ID

Not Available

PubChem Compound

4276

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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. doi: 10.1016/j.toxlet.2005.01.012. [PubMed:15795093 ]
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. doi: 10.1021/jf020946n. [PubMed:12617584 ]
Xiao WW, Zhang HL, Wang CF, Chen Y, Zhan R, Li D, Shao LD: Chemical Synthesis Enables the Configurational Determination of Myristriol, a Highly Oxygenated Phenylpropanoid from Myristica fragrans Houtt. Chem Biodivers. 2023 Mar;20(3):e202201075. doi: 10.1002/cbdv.202201075. Epub 2023 Feb 20. [PubMed:36762483 ]
DOI: 10.1002/cbdv.202201075
PMID: 36762483

Showing NP-Card for Myristicin (NP0048364)

MOL for NP0048364 (Myristicin)

3D MOL for NP0048364 (Myristicin)

3D SDF for NP0048364 (Myristicin)

3D-SDF for NP0048364 (Myristicin)

PDB for NP0048364 (Myristicin)

3D PDB for NP0048364 (Myristicin)

SMILES for NP0048364 (Myristicin)

INCHI for NP0048364 (Myristicin)

Structure for NP0048364 (Myristicin)

3D Structure for NP0048364 (Myristicin)