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Showing metabocard for Phenethyl isocyanate (HMDB0256402)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 16:50:08 UTC
Update Date2021-09-26 23:12:02 UTC
HMDB IDHMDB0256402
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhenethyl isocyanate
Description2-phenylethyl isocyanate belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Based on a literature review very few articles have been published on 2-phenylethyl isocyanate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phenethyl isocyanate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phenethyl isocyanate 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 HMDB0256402 (Phenethyl isocyanate)


  Mrv1652306031608172D          

 11 11  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  2  0  0  0  0
M  END
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3D MOL for HMDB0256402 (Phenethyl isocyanate)

HMDB0256402
     RDKit          3D
Phenethyl isocyanate
 20 20  0  0  0  0  0  0  0  0999 V2000
    4.5379    0.1514   -1.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8952   -0.3314   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323   -0.7882    0.7714 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -0.9401    0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2011    0.3776    0.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2791    0.3084    0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8928   -0.1185   -0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -0.1834   -1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9976    0.1861    0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4038    0.6142    1.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202    0.6734    1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940   -1.1298    1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4527   -1.7154    0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942    0.6341   -0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    1.1389    0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -0.4118   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8063   -0.5146   -1.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0807    0.1424    0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634    0.9056    2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5021    1.0012    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
Download

3D SDF for HMDB0256402 (Phenethyl isocyanate)


  Mrv1652306031608172D          

 11 11  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256402

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C=NCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2

> <INCHI_KEY>
HACRKYQRZABURO-UHFFFAOYSA-N

> <FORMULA>
C9H9NO

> <MOLECULAR_WEIGHT>
147.177

> <EXACT_MASS>
147.068413914

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.78849795376566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-isocyanatoethyl)benzene

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.9705147920000001

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9371588605590193

> <JCHEM_POLAR_SURFACE_AREA>
29.43

> <JCHEM_REFRACTIVITY>
42.7058

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylethyl isocyanate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0256402 (Phenethyl isocyanate)

HMDB0256402
     RDKit          3D
Phenethyl isocyanate
 20 20  0  0  0  0  0  0  0  0999 V2000
    4.5379    0.1514   -1.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8952   -0.3314   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323   -0.7882    0.7714 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -0.9401    0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2011    0.3776    0.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2791    0.3084    0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8928   -0.1185   -0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -0.1834   -1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9976    0.1861    0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4038    0.6142    1.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202    0.6734    1.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940   -1.1298    1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4527   -1.7154    0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942    0.6341   -0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700    1.1389    0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -0.4118   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8063   -0.5146   -1.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0807    0.1424    0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634    0.9056    2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5021    1.0012    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
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PDB for HMDB0256402 (Phenethyl isocyanate)

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8   10   11                                                       
CONECT    9    4    5    6                                                  
CONECT   10    7    8                                                       
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0256402 (Phenethyl isocyanate)

COMPND    HMDB0256402
HETATM    1  O1  UNL     1       4.538   0.151  -1.109  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.895  -0.331  -0.185  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.232  -0.788   0.771  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.789  -0.940   0.737  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.201   0.378   0.240  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.279   0.308   0.175  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.893  -0.118  -0.983  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.277  -0.183  -1.045  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.998   0.186   0.068  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.404   0.614   1.231  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.020   0.673   1.277  1.00  0.00           C  
HETATM   12  H1  UNL     1       1.394  -1.130   1.748  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.453  -1.715   0.039  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.594   0.634  -0.763  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.470   1.139   0.993  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.343  -0.412  -1.865  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.806  -0.515  -1.938  1.00  0.00           H  
HETATM   18  H7  UNL     1      -4.081   0.142   0.040  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.963   0.906   2.108  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.502   1.001   2.162  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3
CONECT    3    4
CONECT    4    5   12   13
CONECT    5    6   14   15
CONECT    6    7    7   11
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   18
CONECT   10   11   11   19
CONECT   11   20
END
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SMILES for HMDB0256402 (Phenethyl isocyanate)

O=C=NCCC1=CC=CC=C1
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INCHI for HMDB0256402 (Phenethyl isocyanate)

InChI=1S/C9H9NO/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-PhenylethylisocyanateChEBI
Phenethyl isocyanateChEBI
Phenylethyl isocyanateChEBI
PhenylethylisocyanateChEBI
2-Phenylethylisocyanic acidGenerator
Phenethyl isocyanic acidGenerator
Phenylethyl isocyanic acidGenerator
Phenylethylisocyanic acidGenerator
2-Phenylethyl isocyanic acidGenerator
Chemical FormulaC9H9NO
Average Molecular Weight147.177
Monoisotopic Molecular Weight147.068413914
IUPAC Name(2-isocyanatoethyl)benzene
Traditional Namephenylethyl isocyanate
CAS Registry NumberNot Available
SMILES
O=C=NCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H9NO/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
InChI KeyHACRKYQRZABURO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Isocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot 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
logP1.81ALOGPS
logP1.97ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.71 m³·mol⁻¹ChemAxon
Polarizability15.79 ųChemAxon
Number of Rings1ChemAxon
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]+131.81430932474
DeepCCS[M-H]-128.58230932474
DeepCCS[M-2H]-165.6230932474
DeepCCS[M+Na]+141.05630932474
AllCCS[M+H]+130.732859911
AllCCS[M+H-H2O]+126.232859911
AllCCS[M+NH4]+134.932859911
AllCCS[M+Na]+136.132859911
AllCCS[M-H]-132.632859911
AllCCS[M+Na-2H]-133.932859911
AllCCS[M+HCOO]-135.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phenethyl isocyanateO=C=NCCC1=CC=CC=C12100.0Standard polar33892256
Phenethyl isocyanateO=C=NCCC1=CC=CC=C11233.8Standard non polar33892256
Phenethyl isocyanateO=C=NCCC1=CC=CC=C11226.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenethyl isocyanate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-2e4cee250ed8f0e844f92021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenethyl isocyanate 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 - Phenethyl isocyanate 10V, Positive-QTOFsplash10-00di-0900000000-ea1fc4584780f0f9be302019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenethyl isocyanate 20V, Positive-QTOFsplash10-0fk9-0900000000-18449251413470627ba82019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenethyl isocyanate 40V, Positive-QTOFsplash10-0k96-9700000000-78ae0d1ab06def6562e02019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenethyl isocyanate 10V, Negative-QTOFsplash10-0002-1900000000-1be4937dfb4d41504f842019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenethyl isocyanate 20V, Negative-QTOFsplash10-0006-9700000000-a7f9e26081ddf2c813e72019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenethyl isocyanate 40V, Negative-QTOFsplash10-0006-9100000000-12286ef69bfa3f9248d82019-02-23Wishart 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 ID141125
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID60067
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 ]