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Showing metabocard for Isocyanic acid (HMDB0253627)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 12:25:33 UTC
Update Date2021-09-26 23:06:58 UTC
HMDB IDHMDB0253627
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsocyanic acid
DescriptionIsocyanic acid, also known as isocyanate or [C(NH)O], belongs to the class of organic compounds known as organooxygen compounds. These are organic compounds containing a bond between a carbon atom and an oxygen atom. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Isocyanic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Isocyanic acid is a potentially toxic compound. 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 poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isocyanic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isocyanic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0253627 (Isocyanic acid)


  Mrv0541 02241204312D          

  3  2  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
M  END
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3D MOL for HMDB0253627 (Isocyanic acid)

HMDB0253627
     RDKit          3D
Isocyanic acid
  4  3  0  0  0  0  0  0  0  0999 V2000
   -0.7348    0.3910   -0.0500 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5075    0.2019    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6741   -0.2156   -0.0365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -0.3773    0.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  1  4  1  0
M  END
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3D SDF for HMDB0253627 (Isocyanic acid)


  Mrv0541 02241204312D          

  3  2  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253627

> <DATABASE_NAME>
hmdb

> <SMILES>
N=C=O

> <INCHI_IDENTIFIER>
InChI=1S/CHNO/c2-1-3/h2H

> <INCHI_KEY>
OWIKHYCFFJSOEH-UHFFFAOYSA-N

> <FORMULA>
CHNO

> <MOLECULAR_WEIGHT>
43.0247

> <EXACT_MASS>
43.005813659

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
3.0848256430285206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
carboximidoyloxidane

> <ALOGPS_LOGP>
-1.32

> <JCHEM_LOGP>
-0.26629559599999997

> <ALOGPS_LOGS>
-0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.480262327005613

> <JCHEM_POLAR_SURFACE_AREA>
40.92

> <JCHEM_REFRACTIVITY>
18.856400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isocyanic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0253627 (Isocyanic acid)

HMDB0253627
     RDKit          3D
Isocyanic acid
  4  3  0  0  0  0  0  0  0  0999 V2000
   -0.7348    0.3910   -0.0500 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5075    0.2019    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6741   -0.2156   -0.0365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -0.3773    0.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  1  4  1  0
M  END
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PDB for HMDB0253627 (Isocyanic acid)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0       3.080   0.000   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.160   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2                                                            
MASTER        0    0    0    0    0    0    0    0    3    0    4    0
END
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3D PDB for HMDB0253627 (Isocyanic acid)

COMPND    HMDB0253627
HETATM    1  N1  UNL     1      -0.735   0.391  -0.050  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.508   0.202   0.077  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.674  -0.216  -0.037  1.00  0.00           O  
HETATM    4  H1  UNL     1      -1.447  -0.377   0.010  1.00  0.00           H  
CONECT    1    2    2    4
CONECT    2    3    3
END
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SMILES for HMDB0253627 (Isocyanic acid)

N=C=O
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INCHI for HMDB0253627 (Isocyanic acid)

InChI=1S/CHNO/c2-1-3/h2H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
[C(NH)O]ChEBI
CarbimideChEBI
HN=C=OChEBI
HNCOChEBI
Hydrogen isocyanateChEBI
ICAChEBI
IsocyanateChEBI
IsocyansaeureChEBI
IsozyansaeureChEBI
MethenamideChEBI
OxidoazanediidocarbonChEBI
Hydrogen isocyanic acidGenerator
Hydrogen isocyanideMeSH
Chemical FormulaCHNO
Average Molecular Weight43.0247
Monoisotopic Molecular Weight43.005813659
IUPAC Namecarboximidoyloxidane
Traditional Nameisocyanic acid
CAS Registry NumberNot Available
SMILES
N=C=O
InChI Identifier
InChI=1S/CHNO/c2-1-3/h2H
InChI KeyOWIKHYCFFJSOEH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organooxygen compounds. These are organic compounds containing a bond between a carbon atom and an oxygen atom.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassNot Available
Direct ParentOrganooxygen compounds
Alternative Parents
Substituents
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-1.3ALOGPS
logP-0.27ChemAxon
logS-0.79ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity18.86 m³·mol⁻¹ChemAxon
Polarizability3.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+113.53730932474
DeepCCS[M-H]-111.75530932474
DeepCCS[M-2H]-147.00230932474
DeepCCS[M+Na]+120.53930932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 20228.1993 minutes33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid753.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid377.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid149.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid301.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid141.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid267.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid326.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)532.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid584.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid86.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid717.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid238.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid341.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate665.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA327.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water287.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isocyanic acidN=C=O1111.9Standard polar33892256
Isocyanic acidN=C=O433.3Standard non polar33892256
Isocyanic acidN=C=O540.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isocyanic acid,1TMS,isomer #1C[Si](C)(C)N=C=O707.0Semi standard non polar33892256
Isocyanic acid,1TMS,isomer #1C[Si](C)(C)N=C=O680.4Standard non polar33892256
Isocyanic acid,1TMS,isomer #1C[Si](C)(C)N=C=O1105.5Standard polar33892256
Isocyanic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C=O960.2Semi standard non polar33892256
Isocyanic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C=O934.4Standard non polar33892256
Isocyanic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C=O1244.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isocyanic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-8cc39ddc30cd2986ef462021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocyanic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocyanic acid 10V, Positive-QTOFsplash10-0006-9000000000-5f0d8b45c37b6532d33c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocyanic acid 20V, Positive-QTOFsplash10-0006-9000000000-5f0d8b45c37b6532d33c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocyanic acid 40V, Positive-QTOFsplash10-0006-9000000000-5f0d8b45c37b6532d33c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocyanic acid 10V, Negative-QTOFsplash10-0006-9000000000-005e171faa9586cdda442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocyanic acid 20V, Negative-QTOFsplash10-0006-9000000000-005e171faa9586cdda442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocyanic acid 40V, Negative-QTOFsplash10-0006-9000000000-005e171faa9586cdda442016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsocyanic acid
METLIN IDNot Available
PubChem Compound6347
PDB IDNot Available
ChEBI ID29202
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]