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Showing metabocard for Phenylacetaldehyde (HMDB0006236)

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enzymes (9) Show 9 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-22 18:42:13 UTC
Update Date2023-02-21 17:17:15 UTC
HMDB IDHMDB0006236
Secondary Accession Numbers
  • HMDB06236
Metabolite Identification
Common NamePhenylacetaldehyde
DescriptionPhenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form. (PMID: 16910727 , 7818768 , 15606130 ).
Structure
Data?1676999835
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006236 (Phenylacetaldehyde)


  Mrv1652309272007322D          

  9  9  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4378    1.9294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
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3D MOL for HMDB0006236 (Phenylacetaldehyde)

HMDB0006236
     RDKit          3D
Phenylacetaldehyde
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.2250   -0.5244   -1.2407 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908   -0.4988   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -0.2083    0.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.0092    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983   -1.0554    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8502   -0.8765   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3120    0.3604   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.4259   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982    1.2497   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243   -0.6843    0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9340    0.6946    1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -1.0929    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2381   -2.0372    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5124   -1.7390   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3031    0.4761   -1.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    2.4015   -0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    2.0994    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0006236 (Phenylacetaldehyde)


  Mrv1652309272007322D          

  9  9  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4378    1.9294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006236

> <DATABASE_NAME>
hmdb

> <SMILES>
O=CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2

> <INCHI_KEY>
DTUQWGWMVIHBKE-UHFFFAOYSA-N

> <FORMULA>
C8H8O

> <MOLECULAR_WEIGHT>
120.1485

> <EXACT_MASS>
120.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.905302752648495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-phenylacetaldehyde

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.4523778529999998

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.982569531878866

> <JCHEM_PKA_STRONGEST_BASIC>
-7.049910347965294

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
36.440200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacetaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0006236 (Phenylacetaldehyde)

HMDB0006236
     RDKit          3D
Phenylacetaldehyde
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.2250   -0.5244   -1.2407 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908   -0.4988   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -0.2083    0.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.0092    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983   -1.0554    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8502   -0.8765   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3120    0.3604   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.4259   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982    1.2497   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243   -0.6843    0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9340    0.6946    1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -1.0929    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2381   -2.0372    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5124   -1.7390   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3031    0.4761   -1.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    2.4015   -0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    2.0994    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0006236 (Phenylacetaldehyde)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       1.083   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   0.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.417   1.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   2.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.750   3.602   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.084   2.832   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.417   3.602   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0006236 (Phenylacetaldehyde)

COMPND    HMDB0006236
HETATM    1  O1  UNL     1       2.225  -0.524  -1.241  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.591  -0.499  -0.081  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.593  -0.208   0.973  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.257   0.009   0.380  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.598  -1.055   0.204  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.850  -0.877  -0.348  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.312   0.360  -0.750  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.453   1.426  -0.572  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.198   1.250  -0.020  1.00  0.00           C  
HETATM   10  H1  UNL     1       3.624  -0.684   0.177  1.00  0.00           H  
HETATM   11  H2  UNL     1       1.934   0.695   1.509  1.00  0.00           H  
HETATM   12  H3  UNL     1       1.564  -1.093   1.673  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.238  -2.037   0.520  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.512  -1.739  -0.478  1.00  0.00           H  
HETATM   15  H6  UNL     1      -3.303   0.476  -1.182  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.803   2.402  -0.883  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.481   2.099   0.119  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   11   12
CONECT    4    5    5    9
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   17
END
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SMILES for HMDB0006236 (Phenylacetaldehyde)

O=CCC1=CC=CC=C1
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INCHI for HMDB0006236 (Phenylacetaldehyde)

InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-oxo-2-PhenylethaneChEBI
2-PhenylacetaldehydeChEBI
2-PhenylethanalChEBI
alpha-PhenylacetaldehydeChEBI
alpha-TolualdehydeChEBI
alpha-Toluic aldehydeChEBI
BenzacetaldehydeChEBI
BenzeneacetaldehydeChEBI
HyacinthinChEBI
PhenacetaldehydeChEBI
Phenylacetic aldehydeChEBI
a-PhenylacetaldehydeGenerator
Α-phenylacetaldehydeGenerator
a-TolualdehydeGenerator
Α-tolualdehydeGenerator
a-Toluic aldehydeGenerator
Α-toluic aldehydeGenerator
.alpha.-toluic aldehydeHMDB
BenzenacetaldehydeHMDB
BenzylcarboxaldehydeHMDB
FEMA no. 2974HMDB
OxophenylethaneHMDB
Phenyl-acetaldehydeHMDB
PhenylethanalHMDB
Chemical FormulaC8H8O
Average Molecular Weight120.1485
Monoisotopic Molecular Weight120.057514878
IUPAC Name2-phenylacetaldehyde
Traditional Namephenylacetaldehyde
CAS Registry Number122-78-1
SMILES
O=CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2
InChI KeyDTUQWGWMVIHBKE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Alpha-hydrogen aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Industrial processNaturally occurring process
Role
Industrial applicationEnvironmental role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point120.5 - 121.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.78HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.08 g/LALOGPS
logP1.75ALOGPS
logP1.45ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)14.98ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.44 m³·mol⁻¹ChemAxon
Polarizability12.91 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
DarkChem[M+H]+123.57931661259
DarkChem[M-H]-119.91831661259
DeepCCS[M+H]+124.62630932474
DeepCCS[M-H]-121.7130932474
DeepCCS[M-2H]-158.41930932474
DeepCCS[M+Na]+133.28330932474
AllCCS[M+H]+124.632859911
AllCCS[M+H-H2O]+119.732859911
AllCCS[M+NH4]+129.132859911
AllCCS[M+Na]+130.432859911
AllCCS[M-H]-123.532859911
AllCCS[M+Na-2H]-125.532859911
AllCCS[M+HCOO]-127.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenylacetaldehydeO=CCC1=CC=CC=C11608.7Standard polar33892256
PhenylacetaldehydeO=CCC1=CC=CC=C1997.4Standard non polar33892256
PhenylacetaldehydeO=CCC1=CC=CC=C11054.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenylacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CC1=CC=CC=C11315.7Semi standard non polar33892256
Phenylacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CC1=CC=CC=C11264.8Standard non polar33892256
Phenylacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CC1=CC=CC=C11634.4Standard polar33892256
Phenylacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CC=CC=C11567.3Semi standard non polar33892256
Phenylacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CC=CC=C11494.8Standard non polar33892256
Phenylacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CC=CC=C11811.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-MS (Non-derivatized)splash10-00kf-9400000000-bec6e42b47ad1306960f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-MS (Non-derivatized)splash10-014l-9700000000-152bdd5b77d6af9657ec2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde EI-B (Non-derivatized)splash10-0006-9000000000-d37cbef4100302e951de2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-MS (Non-derivatized)splash10-00kf-9400000000-bec6e42b47ad1306960f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-MS (Non-derivatized)splash10-014l-9700000000-152bdd5b77d6af9657ec2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-EI-TOF (Non-derivatized)splash10-00kf-9400000000-e75d2f0bf82f16a803882017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-EI-TOF (Non-derivatized)splash10-00kf-9400000000-32573b7f6ab690a27e3e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-EI-TOF (Non-derivatized)splash10-0006-5900000000-21e85148d15d190553c42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-EI-TOF (Non-derivatized)splash10-0006-5900000000-4471e0916a32cf4df7ac2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-EI-TOF (Non-derivatized)splash10-0006-5900000000-650012e69d0a89a2fd4a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenylacetaldehyde GC-EI-TOF (Non-derivatized)splash10-0006-5900000000-c80b65e383f833509e0f2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylacetaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-b3923f5fae42c664ac4a2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylacetaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylacetaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-e7ef9a5c5a6cc5674cd12014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylacetaldehyde Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0udi-4900000000-5001b07cef2fed3caa2c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylacetaldehyde Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004i-9100000000-048e2f1b42f7bd5104be2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylacetaldehyde Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0fb9-9000000000-fc1fbd4e7c49f44ba7642012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylacetaldehyde EI-B (HITACHI M-80A) , Positive-QTOFsplash10-0006-9000000000-bc0fa2967da6872f3a472012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenylacetaldehyde 35V, Positive-QTOFsplash10-0ufr-9700000000-507b63b585578b6706282021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 10V, Positive-QTOFsplash10-00di-0900000000-8c96fee71b311d7511812015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 20V, Positive-QTOFsplash10-0fk9-2900000000-4b405668c302f69a4bc72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 40V, Positive-QTOFsplash10-0ufr-9300000000-fe46a418a2f0124566c32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 10V, Negative-QTOFsplash10-014i-0900000000-4e064e0123dc18b6136a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 20V, Negative-QTOFsplash10-014i-1900000000-02fff0bd874e6e8616bb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 40V, Negative-QTOFsplash10-004l-9200000000-340c7a60a7708fa801f12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 10V, Positive-QTOFsplash10-002f-9000000000-e37fda57674e1a53ea102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 20V, Positive-QTOFsplash10-0006-9000000000-2071e5b3f45157a1da9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 40V, Positive-QTOFsplash10-002f-9100000000-219bfc0a5188714799772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 10V, Negative-QTOFsplash10-00kf-9300000000-3fb47a0274f5792b4bd12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 20V, Negative-QTOFsplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylacetaldehyde 40V, Negative-QTOFsplash10-0006-9000000000-cc66f13f72898a397be62021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified205.301 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified291.306 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified263.563 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal		 details
FecesDetected and Quantified0-59703.894 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
FecesDetected and Quantified0-82314.802 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDDB02178
Phenol Explorer Compound IDNot Available
FooDB IDFDB012238
KNApSAcK IDC00007535
Chemspider ID13876539
KEGG Compound IDC00601
BioCyc IDPHENYLACETALDEHYDE
BiGG ID35469
Wikipedia LinkPhenylacetaldehyde
METLIN IDNot Available
PubChem Compound998
PDB IDNot Available
ChEBI ID16424
Food Biomarker OntologyNot Available
VMH IDPACALD
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSun Zhirong; Hu Xiang; Zhou Ding Wastewater minimization in indirect electrochemical synthesis of phenylacetaldehyde. TheScientificWorldJournal (2002), 2 48-52.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Watson WP, Munter T, Golding BT: A new role for glutathione: protection of vitamin B12 from depletion by xenobiotics. Chem Res Toxicol. 2004 Dec;17(12):1562-7. [PubMed:15606130 ]
  2. Cho IH, Kim SY, Choi HK, Kim YS: Characterization of aroma-active compounds in raw and cooked pine-mushrooms (Tricholoma matsutake Sing.). J Agric Food Chem. 2006 Aug 23;54(17):6332-5. [PubMed:16910727 ]
  3. Sumner SJ, Fennell TR: Review of the metabolic fate of styrene. Crit Rev Toxicol. 1994;24 Suppl:S11-33. [PubMed:7818768 ]

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
2. Amine oxidase [flavin-containing] A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
3. Aldehyde dehydrogenase, dimeric NADP-preferring
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails
Enzyme Details
4. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails
Enzyme Details
5. Amiloride-sensitive amine oxidase [copper-containing]
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Enzyme Details
6. Membrane primary amine oxidase
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
7. Retina-specific copper amine oxidase
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
8. Aldehyde dehydrogenase family 3 member B2
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails
Enzyme Details
9. Aldehyde dehydrogenase family 3 member B1
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails