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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-12 19:23:56 UTC
Update Date2021-09-07 16:45:35 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
Data?1586372492
Synonyms
ValueSource
1-PropanalChEBI
Aldehyde propioniqueChEBI
C2H5CHOChEBI
MethylacetaldehydeChEBI
N-PropanalChEBI
N-PropionaldehydeChEBI
PropaldehydeChEBI
PropanaldehydeChEBI
PropionalChEBI
PropionaldehydeChEBI
Propionic aldehydeChEBI
Propyl aldehydeChEBI
PropylaldehydeChEBI
Propylic aldehydeChEBI
1-PropanoneHMDB
PropanalaldehydeHMDB
ProprionaldehydeHMDB
Propionaldehyde, 1-14C-labeledHMDB
Propionaldehyde, 2-14C-labeledHMDB
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
Disposition

Biological location

Source

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
PropertyValueSource
Water Solubility146 g/LALOGPS
logP0.31ALOGPS
logP0.32ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)17.32ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.35 m³·mol⁻¹ChemAxon
Polarizability6.36 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]+118.5930932474
DeepCCS[M-H]-116.75830932474
DeepCCS[M-2H]-152.06830932474
DeepCCS[M+Na]+125.97930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PropanalCCC=O753.0Standard polar33892256
PropanalCCC=O453.2Standard non polar33892256
PropanalCCC=O480.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Propanal,1TMS,isomer #1CC=CO[Si](C)(C)C745.2Semi standard non polar33892256
Propanal,1TMS,isomer #1CC=CO[Si](C)(C)C685.3Standard non polar33892256
Propanal,1TMS,isomer #1CC=CO[Si](C)(C)C855.1Standard polar33892256
Propanal,1TBDMS,isomer #1CC=CO[Si](C)(C)C(C)(C)C951.9Semi standard non polar33892256
Propanal,1TBDMS,isomer #1CC=CO[Si](C)(C)C(C)(C)C930.7Standard non polar33892256
Propanal,1TBDMS,isomer #1CC=CO[Si](C)(C)C(C)(C)C1063.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Propanal EI-B (Non-derivatized)splash10-057i-9000000000-8f67579ff6f9ff36070f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propanal EI-B (Non-derivatized)splash10-057i-9000000000-8f67579ff6f9ff36070f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propanal GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-dd28a1a5691e42b989442016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propanal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-666a0ffacd21addbc6122015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Propanal Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-addcd7ef3249da0c30062012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propanal Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-052f-9000000000-b7cab81070aff00497c62012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propanal Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4l-9000000000-e9e60e8897ba5a8e14ee2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propanal EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-057i-9000000000-52017f5345efcb7c9e182012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 10V, Positive-QTOFsplash10-0a4i-9000000000-971c212b11d2cbddac7d2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 20V, Positive-QTOFsplash10-0a4l-9000000000-86839cd4133b824334ac2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 40V, Positive-QTOFsplash10-0006-9000000000-2bde2476aa46442e72502015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 10V, Negative-QTOFsplash10-0a4i-9000000000-4a423491df240f1b65942015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 20V, Negative-QTOFsplash10-0a4i-9000000000-bcb4e63c226b3b43a90d2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 40V, Negative-QTOFsplash10-052o-9000000000-b8b5099c348f5e885f6e2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 10V, Negative-QTOFsplash10-0a4i-9000000000-6e3379842f4da69e8e2b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 20V, Negative-QTOFsplash10-0a4i-9000000000-6e3379842f4da69e8e2b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 40V, Negative-QTOFsplash10-052f-9000000000-214db2e33bae0f6596902021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 10V, Positive-QTOFsplash10-0a4i-9000000000-cd36cdb80b20021fec3b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 20V, Positive-QTOFsplash10-052f-9000000000-ea4dc2c9ba22fa57f2652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propanal 40V, Positive-QTOFsplash10-0006-9000000000-84b5273da6b73dbe78de2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.17 - 0.69 uMAdult (>18 years old)Not SpecifiedNormal 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)BothNormal 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 QuantifiedNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis 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 but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
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 ]
  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)Download (PDF)
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

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
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