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Showing metabocard for Propanal (HMDB0003366)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-12 19:23:56 UTC
Update Date2023-02-21 17:16:38 UTC
HMDB IDHMDB0003366
Secondary Accession Numbers
  • HMDB03366
Metabolite Identification
Common NamePropanal
DescriptionPropanal, also known as N-propionaldehyde or C2H5CHO, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. Propanal exists in all living species, ranging from bacteria to humans. Propanal is an alcohol, cocoa, and earthy tasting compound. Outside of the human body, Propanal is found, on average, in the highest concentration within wild celeries and carrots. Propanal has also been detected, but not quantified in several different foods, such as purple lavers, black salsifies, strawberry guava, grapefruit/pummelo hybrids, and alaska wild rhubarbs. It is an aldehyde that consists of ethane bearing a formyl substituent.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003366 (Propanal)

  Mrv1652309042000292D          

  4  3  0  0  0  0            999 V2000
   -2.1649    0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7360    0.9035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
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3D MOL for HMDB0003366 (Propanal)

HMDB0003366
     RDKit          3D
Propanal
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.1318    0.0484   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2401   -0.5609   -0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2738    0.4547    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9365    1.5644    0.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7104   -0.5347    0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6815    0.1072   -0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0487    1.0893    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.4377    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -0.9006   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    0.1699    0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
M  END
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3D SDF for HMDB0003366 (Propanal)

  Mrv1652309042000292D          

  4  3  0  0  0  0            999 V2000
   -2.1649    0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7360    0.9035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003366

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3

> <INCHI_KEY>
NBBJYMSMWIIQGU-UHFFFAOYSA-N

> <FORMULA>
C3H6O

> <MOLECULAR_WEIGHT>
58.0791

> <EXACT_MASS>
58.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
6.364779371580674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
propanal

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
0.3185738803333332

> <ALOGPS_LOGS>
0.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.322359249671507

> <JCHEM_PKA_STRONGEST_BASIC>
-6.938105699195357

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
16.3452

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propionaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0003366 (Propanal)

HMDB0003366
     RDKit          3D
Propanal
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.1318    0.0484   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2401   -0.5609   -0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2738    0.4547    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9365    1.5644    0.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7104   -0.5347    0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6815    0.1072   -0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0487    1.0893    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.4377    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -0.9006   -1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059    0.1699    0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
M  END
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PDB for HMDB0003366 (Propanal)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -4.041   1.687   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.375   0.917   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.708   0.917   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.374   1.687   0.000  0.00  0.00           O+0
CONECT    1    3    2                                                       
CONECT    2    1                                                            
CONECT    3    1    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 HMDB0003366 (Propanal)

COMPND    HMDB0003366
HETATM    1  C1  UNL     1      -1.132   0.048  -0.041  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.240  -0.561  -0.157  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.274   0.455   0.171  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.936   1.564   0.470  1.00  0.00           O  
HETATM    5  H1  UNL     1      -1.710  -0.535   0.708  1.00  0.00           H  
HETATM    6  H2  UNL     1      -1.681   0.107  -0.982  1.00  0.00           H  
HETATM    7  H3  UNL     1      -1.049   1.089   0.373  1.00  0.00           H  
HETATM    8  H4  UNL     1       0.357  -1.438   0.537  1.00  0.00           H  
HETATM    9  H5  UNL     1       0.459  -0.901  -1.210  1.00  0.00           H  
HETATM   10  H6  UNL     1       2.306   0.170   0.132  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    8    9
CONECT    3    4    4   10
END
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SMILES for HMDB0003366 (Propanal)

CCC=O
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INCHI for HMDB0003366 (Propanal)

InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC3H6O
Average Molecular Weight58.0791
Monoisotopic Molecular Weight58.041864814
IUPAC Namepropanal
Traditional Namepropionaldehyde
CAS Registry Number123-38-6
SMILES
CCC=O
InChI Identifier
InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3
InChI KeyNBBJYMSMWIIQGU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Environmental roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-80 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility306 mg/mL at 25 °CNot Available
LogP0.59HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
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 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
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 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
  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 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012083
KNApSAcK IDNot Available
Chemspider ID512
KEGG Compound IDC00479
BioCyc IDCPD-665
BiGG IDNot Available
Wikipedia LinkPropanal
METLIN ID6906
PubChem Compound527
PDB IDNot Available
ChEBI ID17153
Food Biomarker OntologyNot Available
VMH IDPPAL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWang, Yan-bin; Yao, Xiao-ming. Development of the process of making propanal from natural gas and light oil. Tianranqi Huagong (2003), 28(1), 8-10,14.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sakura N, Nishimura S, Fujita N, Namera A, Yashiki M, Kojima T: Determination of acrolein in human urine by headspace gas chromatography and mass spectrometry. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):209-12. [PubMed:9869381 ]
  2. Takamoto S, Sakura N, Yashiki M, Kojima T: Determination of acrolein by headspace solid-phase microextraction gas chromatography and mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001 Jul 5;758(1):123-8. [PubMed:11482731 ]
  3. Nakashima K, Hidaka Y, Yoshida T, Kuroda N, Akiyama S: High-performance liquid chromatographic determination of short-chain aliphatic aldehydes using 4-(N,N-dimethylaminosulphonyl)-7-hydrazino-2,1, 3-benzoxadiazole as a fluorescence reagent. J Chromatogr B Biomed Appl. 1994 Nov 18;661(2):205-10. [PubMed:7894659 ]
  4. Holley AE, Walker MK, Cheeseman KH, Slater TF: Measurement of n-alkanals and hydroxyalkenals in biological samples. Free Radic Biol Med. 1993 Sep;15(3):281-9. [PubMed:8406128 ]

Enzymes

Enzyme Details
1. Carbonyl reductase [NADPH] 1
General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
Propanal → Propyl alcoholdetails
Enzyme Details
2. Retinal dehydrogenase 2
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal efficiently (By similarity).
Gene Name:
ALDH1A2
Uniprot ID:
O94788
Molecular weight:
54672.24