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Showing NP-Card for Methyl isocyanate  (NP0045152)

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Record Information
Version1.0
Created at2022-03-10 18:58:51 UTC
Updated at2022-03-10 22:21:44 UTC
NP-MRD IDNP0045152
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl isocyanate 
DescriptionIsocyanatomethane or methyl isocyanate, also known as iso-cyanatomethane or methyl carbonimide, belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOCN or its hydrocarbyl derivatives RN=C=O. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Isocyanatomethane is a colorless, poisonous, lachrymatory (tearing agent), flammable liquid. It is soluble in water, but it also reacts with it. Isocyanatomethane is an intermediate in the production of carbamate pesticides (such as carbaryl, carbofuran, methomyl, and aldicarb). It has also been used in the production of rubbers and adhesives. As a highly toxic and irritating material, it is extremely hazardous to human health. Cyanide is an inhibitor of the cytochrome C oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). As a result, the electron transport chain is disrupted, and the cell can no longer aerobically produce ATP for energy. Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Isocyanatomethane has been detected in the volatile fraction of Cannabis sativa samples, obtained from police seizures (PMID: 26657499 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045152 (Methyl isocyanate )


  Mrv1652303202019002D          

  4  3  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  2  0  0  0  0
M  END
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3D MOL for NP0045152 (Methyl isocyanate )

     RDKit          3D

  7  6  0  0  0  0  0  0  0  0999 V2000
   -0.8581   -0.0496    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719    0.1963   -0.6554 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4957    0.2464   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -0.1220    0.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7734   -0.5374    0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5327   -0.6822   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702    0.9486    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
M  END
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3D SDF for NP0045152 (Methyl isocyanate )


  Mrv1652303202019002D          

  4  3  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN=C=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H3NO/c1-3-2-4/h1H3

> <INCHI_KEY>
HAMGRBXTJNITHG-UHFFFAOYSA-N

> <FORMULA>
C2H3NO

> <MOLECULAR_WEIGHT>
57.0513

> <EXACT_MASS>
57.021463723

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
5.047279703556356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
isocyanatomethane

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-0.0426195303333334

> <ALOGPS_LOGS>
-0.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.075707597168193

> <JCHEM_POLAR_SURFACE_AREA>
29.43

> <JCHEM_REFRACTIVITY>
13.338199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl isocyanate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045152 (Methyl isocyanate )

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PDB for NP0045152 (Methyl isocyanate )
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.540   0.000   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.540   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END

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3D PDB for NP0045152 (Methyl isocyanate )
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SMILES for NP0045152 (Methyl isocyanate )
CN=C=O
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INCHI for NP0045152 (Methyl isocyanate )
InChI=1S/C2H3NO/c1-3-2-4/h1H3
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View in JSmol
Synonyms
ValueSource
Iso-cyanatomethaneChEBI
Isocyanate de methyleChEBI
IsocyanatomethaneChEBI
Methyl carbonimideChEBI
Methyl isocyanideChEBI
MethylcarbylamineChEBI
MICChEBI
Isocyanic acid de methyleGenerator
Methyl isocyanic acidGenerator
MethylisocyanateMeSH
Chemical FormulaC2H3NO
Average Mass57.0513 Da
Monoisotopic Mass57.02146 Da
IUPAC Nameisocyanatomethane
Traditional Namemethyl isocyanate
CAS Registry Number30108-95-3
SMILES
CN=C=O
InChI Identifier
InChI=1S/C2H3NO/c1-3-2-4/h1H3
InChI KeyHAMGRBXTJNITHG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cannabis sativaNULL
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOC#N or its hydrocarbyl derivatives RN=C=O.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassIsocyanates  
Direct ParentIsocyanates  
Alternative Parents
Substituents
  • Isocyanate
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Imine
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.24ALOGPS
logP-0.043ChemAxon
logS-0.19ALOGPS
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity13.34 m³·mol⁻¹ChemAxon
Polarizability5.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB12765  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl isocyanate  
METLIN IDNot Available
PubChem Compound12228  
PDB IDNot Available
ChEBI ID59059  
Good Scents IDNot Available
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499  ] 
  2. Boutin M, Lesage J, Ostiguy C, Pauluhn J: Validation of a solvent-free sampler for the determination of low molecular weight aliphatic isocyanates under thermal degradation conditions. J Occup Environ Hyg. 2005 Sep;2(9):456-61. doi: 10.1080/15459620500240626. [PubMed:16091349  ] 
  3. Svensson-Elfsmark L, Koch BL, Gustafsson A, Bucht A: Rats repeatedly exposed to toluene diisocyanate exhibit immune reactivity against methyl isocyanate-protein conjugates. Int Arch Allergy Immunol. 2009;150(3):229-36. doi: 10.1159/000222675. Epub 2009 Jun 3. [PubMed:19494520  ] 
  4. Shrivastava R, Yasir M, Tripathi M, Singh P: In silico interaction of methyl isocyanate with immune protein responsible for Mycobacterium tuberculosis infection using molecular docking. Toxicol Ind Health. 2016 Jan;32(1):162-7. doi: 10.1177/0748233713498447. Epub 2013 Sep 30. [PubMed:24081639  ] 
  5. Karol MH, Taskar S, Gangal S, Rubanoff BF, Kamat SR: The antibody response to methyl isocyanate: experimental and clinical findings. Environ Health Perspect. 1987 Jun;72:169-75. doi: 10.1289/ehp.8772169. [PubMed:3622432  ] 
  6. Karol MH, Hauth BA: Use of hexyl isocyanate antigen to detect antibodies to hexamethylene diisocyanate (HDI) in sensitized guinea pigs and in a sensitized worker. Fundam Appl Toxicol. 1982 May-Jun;2(3):108-13. doi: 10.1016/s0272-0590(82)80090-0. [PubMed:6821040  ]