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Showing metabocard for Isobutyl nitrite (HMDB0253612)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 12:24:34 UTC
Update Date2021-09-26 23:06:56 UTC
HMDB IDHMDB0253612
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsobutyl nitrite
Descriptionisobutyl nitrite, also known as IBN, belongs to the class of organic compounds known as organic o-nitroso compounds. These are organic compounds containing a n-nitroso group -ON=O. Based on a literature review very few articles have been published on isobutyl nitrite. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isobutyl nitrite is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isobutyl nitrite 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 HMDB0253612 (Isobutyl nitrite)


  Mrv1572004221603042D          

  7  6  0  0  0  0            999 V2000
   -1.8414   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0253612 (Isobutyl nitrite)

HMDB0253612
     RDKit          3D
Isobutyl nitrite
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.3483    1.3936   -0.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4233    0.1838    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8408   -0.3642    0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834   -0.8777    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508   -0.2921    0.0855 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176   -0.9203   -0.2568 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446   -0.3167   -0.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036    2.1730    0.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154    1.6969   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7519    1.0887   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1903    0.4861    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -0.3261   -0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480   -1.3760    0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5092    0.3865    0.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -1.7077    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3330   -1.2278   -0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
M  END
Download

3D SDF for HMDB0253612 (Isobutyl nitrite)


  Mrv1572004221603042D          

  7  6  0  0  0  0            999 V2000
   -1.8414   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253612

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CON=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3

> <INCHI_KEY>
APNSGVMLAYLYCT-UHFFFAOYSA-N

> <FORMULA>
C4H9NO2

> <MOLECULAR_WEIGHT>
103.121

> <EXACT_MASS>
103.063328534

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.6096644214599

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpropyl nitrite

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.7884015366666666

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9565222044660313

> <JCHEM_POLAR_SURFACE_AREA>
38.66

> <JCHEM_REFRACTIVITY>
26.9482

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isobutyl nitrite

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0253612 (Isobutyl nitrite)

HMDB0253612
     RDKit          3D
Isobutyl nitrite
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.3483    1.3936   -0.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4233    0.1838    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8408   -0.3642    0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834   -0.8777    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508   -0.2921    0.0855 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176   -0.9203   -0.2568 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446   -0.3167   -0.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036    2.1730    0.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154    1.6969   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7519    1.0887   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1903    0.4861    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -0.3261   -0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480   -1.3760    0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5092    0.3865    0.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -1.7077    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3330   -1.2278   -0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
M  END
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PDB for HMDB0253612 (Isobutyl nitrite)

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -3.437  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.104   0.976   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.897  -1.334   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       3.231  -0.564   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    4    7                                                       
CONECT    4    1    2    3                                                  
CONECT    5    6    7                                                       
CONECT    6    5                                                            
CONECT    7    3    5                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0253612 (Isobutyl nitrite)

COMPND    HMDB0253612
HETATM    1  C1  UNL     1      -0.348   1.394  -0.412  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.423   0.184   0.497  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.841  -0.364   0.362  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.583  -0.878   0.025  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.851  -0.292   0.085  1.00  0.00           O  
HETATM    6  N1  UNL     1       3.018  -0.920  -0.257  1.00  0.00           N  
HETATM    7  O2  UNL     1       4.045  -0.317  -0.548  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.004   2.173   0.052  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.715   1.697  -0.447  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.752   1.089  -1.396  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.190   0.486   1.531  1.00  0.00           H  
HETATM   12  H5  UNL     1      -2.070  -0.326  -0.727  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.948  -1.376   0.744  1.00  0.00           H  
HETATM   14  H7  UNL     1      -2.509   0.387   0.841  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.541  -1.708   0.772  1.00  0.00           H  
HETATM   16  H9  UNL     1       0.333  -1.228  -0.989  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4   11
CONECT    3   12   13   14
CONECT    4    5   15   16
CONECT    5    6
CONECT    6    7    7
END
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SMILES for HMDB0253612 (Isobutyl nitrite)

CC(C)CON=O
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INCHI for HMDB0253612 (Isobutyl nitrite)

InChI=1S/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
IBNChEBI
IsobutylnitritChEBI
Nitrous acid, 2-methylpropyl esterChEBI
Nitrous acid, isobutyl esterChEBI
Isobutyl nitriteMeSH
Chemical FormulaC4H9NO2
Average Molecular Weight103.121
Monoisotopic Molecular Weight103.063328534
IUPAC Name2-methylpropyl nitrite
Traditional Nameisobutyl nitrite
CAS Registry NumberNot Available
SMILES
CC(C)CON=O
InChI Identifier
InChI=1S/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3
InChI KeyAPNSGVMLAYLYCT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic o-nitroso compounds. These are organic compounds containing a n-nitroso group -ON=O.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic nitroso compounds
Direct ParentOrganic O-nitroso compounds
Alternative Parents
Substituents
  • Organic o-nitroso compound
  • Alkyl nitrite
  • Organic nitrite
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
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
logP1.41ALOGPS
logP1.79ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.66 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.95 m³·mol⁻¹ChemAxon
Polarizability10.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+126.50230932474
DeepCCS[M-H]-124.28330932474
DeepCCS[M-2H]-160.33430932474
DeepCCS[M+Na]+134.81530932474
AllCCS[M+H]+123.832859911
AllCCS[M+H-H2O]+119.532859911
AllCCS[M+NH4]+127.832859911
AllCCS[M+Na]+128.932859911
AllCCS[M-H]-124.832859911
AllCCS[M+Na-2H]-128.832859911
AllCCS[M+HCOO]-133.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isobutyl nitriteCC(C)CON=O680.2Standard polar33892256
Isobutyl nitriteCC(C)CON=O562.3Standard non polar33892256
Isobutyl nitriteCC(C)CON=O715.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyl nitrite GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r6-9000000000-24f9f869535f5593e4442021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyl nitrite 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 - Isobutyl nitrite 10V, Positive-QTOFsplash10-0udi-2900000000-3bd3181f7c3d8d0db66c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 20V, Positive-QTOFsplash10-0k96-9200000000-24f41233615ccf4becd92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 40V, Positive-QTOFsplash10-0a4i-9000000000-2363559220a3d0aa88752016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 10V, Negative-QTOFsplash10-0udi-1900000000-3205b9c82a9b369c168a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 20V, Negative-QTOFsplash10-0udi-6900000000-ed3630c89d35da78940f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 40V, Negative-QTOFsplash10-0w9a-9100000000-4c872c09eb27ff571a882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 10V, Positive-QTOFsplash10-0a4i-9000000000-ff52e67c20c817333ab22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 20V, Positive-QTOFsplash10-0a4i-9000000000-3bc6bca950c7d0a98e492021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 40V, Positive-QTOFsplash10-0002-9000000000-9c9548aa9e3bd24b86662021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 10V, Negative-QTOFsplash10-0udi-1900000000-1a56145a28dc48e1f5822021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 20V, Negative-QTOFsplash10-0002-9000000000-a0441e6336543cb884232021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl nitrite 40V, Negative-QTOFsplash10-0002-9000000000-f0939c070ab3e8d9c1b32021-10-12Wishart 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 ID10493
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsobutyl nitrite
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID46643
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 ]