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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:09:09 UTC
Update Date2023-02-21 17:17:51 UTC
HMDB IDHMDB0012882
Secondary Accession Numbers
  • HMDB12882
Metabolite Identification
Common NameAdipate semialdehyde
DescriptionAdipate semialdehyde, also known as 6-oxohexanoate or 5-formylvaleric acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review a small amount of articles have been published on Adipate semialdehyde.
Structure
Data?1676999871
Synonyms
ValueSource
1-Hexanal-6-carboxylic acidChEBI
5-Carbohydroxy-1-pentanalChEBI
5-Formylvaleric acidChEBI
6-Hydroxy caproic acidChEBI
Adipic acid monoaldehydeChEBI
Adipic acid semialdehydeChEBI
Adipic monoaldehydeChEBI
Adipic semialdehydeChEBI
Hexan-1-one-6-carboxylateKegg
6-OxohexanoateKegg
6-Oxohexanoic acidKegg
1-Hexanal-6-carboxylateGenerator
5-FormylvalerateGenerator
6-Hydroxy caproateGenerator
Adipate monoaldehydeGenerator
Hexan-1-one-6-carboxylic acidGenerator
Adipate semialdehydeGenerator
Chemical FormulaC6H10O3
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
IUPAC Name6-oxohexanoic acid
Traditional Name6-oxohexanoic acid
CAS Registry Number928-81-4
SMILES
OC(=O)CCCCC=O
InChI Identifier
InChI=1S/C6H10O3/c7-5-3-1-2-4-6(8)9/h5H,1-4H2,(H,8,9)
InChI KeyPNPPVRALIYXJBW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Alpha-hydrogen aldehyde
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
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
Water Solubility29.8 g/LALOGPS
logP0.42ALOGPS
logP0.33ChemAxon
logS-0.64ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity31.81 m³·mol⁻¹ChemAxon
Polarizability13.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.16131661259
DarkChem[M-H]-123.31331661259
DeepCCS[M+H]+129.97630932474
DeepCCS[M-H]-127.75830932474
DeepCCS[M-2H]-163.60330932474
DeepCCS[M+Na]+138.57830932474
AllCCS[M+H]+130.132859911
AllCCS[M+H-H2O]+126.032859911
AllCCS[M+NH4]+133.932859911
AllCCS[M+Na]+135.032859911
AllCCS[M-H]-129.232859911
AllCCS[M+Na-2H]-131.832859911
AllCCS[M+HCOO]-134.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Adipate semialdehydeOC(=O)CCCCC=O2242.5Standard polar33892256
Adipate semialdehydeOC(=O)CCCCC=O1026.3Standard non polar33892256
Adipate semialdehydeOC(=O)CCCCC=O1184.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Adipate semialdehyde,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC=O1279.0Semi standard non polar33892256
Adipate semialdehyde,1TMS,isomer #2C[Si](C)(C)OC=CCCCC(=O)O1400.7Semi standard non polar33892256
Adipate semialdehyde,2TMS,isomer #1C[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C1465.9Semi standard non polar33892256
Adipate semialdehyde,2TMS,isomer #1C[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C1439.5Standard non polar33892256
Adipate semialdehyde,2TMS,isomer #1C[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C1528.5Standard polar33892256
Adipate semialdehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC=O1519.2Semi standard non polar33892256
Adipate semialdehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=CCCCC(=O)O1652.8Semi standard non polar33892256
Adipate semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C(C)(C)C1882.5Semi standard non polar33892256
Adipate semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C(C)(C)C1878.1Standard non polar33892256
Adipate semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C(C)(C)C1789.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Adipate semialdehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aru-9100000000-2e4ea40055a35c1a39c72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adipate semialdehyde GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9600000000-f6045459ae7ea2c05e1a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adipate semialdehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adipate semialdehyde 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 - Adipate semialdehyde 10V, Positive-QTOFsplash10-03di-2900000000-e4846c918bd86e8ad81d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 20V, Positive-QTOFsplash10-03dr-9500000000-96dbf4ca779b71f9a84b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 40V, Positive-QTOFsplash10-0006-9000000000-4c6838822f8b78f24b692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 10V, Negative-QTOFsplash10-004i-1900000000-42b217c60c3cfe90285b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 20V, Negative-QTOFsplash10-01t9-4900000000-ee529e88593da368017e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 40V, Negative-QTOFsplash10-0006-9000000000-675d5ad3419d73c75c552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 10V, Positive-QTOFsplash10-01p9-9200000000-2041a85784934bc9906d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 20V, Positive-QTOFsplash10-05mo-9000000000-65b8e816b104e8e2ba342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 40V, Positive-QTOFsplash10-0006-9000000000-3b3a65665b8b5df242d22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 10V, Negative-QTOFsplash10-01t9-1900000000-1177328a289f7bb588192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 20V, Negative-QTOFsplash10-03el-9600000000-b4261ddef35b4c94899e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adipate semialdehyde 40V, Negative-QTOFsplash10-0006-9000000000-c0aee2e627df9f8d2be42021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H 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+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
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029197
KNApSAcK IDNot Available
Chemspider ID389748
KEGG Compound IDC06102
BioCyc ID6-OXO-HEXANOATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440918
PDB IDNot Available
ChEBI ID2490
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a variety of aromatic and aliphatic aldehydes to their corresponding alcohols. Catalyzes the reduction of mevaldate to mevalonic acid and of glyceraldehyde to glycerol. Has broad substrate specificity. In vitro substrates include succinic semialdehyde, 4-nitrobenzaldehyde, 1,2-naphthoquinone, methylglyoxal, and D-glucuronic acid. Plays a role in the activation of procarcinogens, such as polycyclic aromatic hydrocarbon trans-dihydrodiols, and in the metabolism of various xenobiotics and drugs, including the anthracyclines doxorubicin (DOX) and daunorubicin (DAUN).
Gene Name:
AKR1A1
Uniprot ID:
P14550
Molecular weight:
36572.71
Reactions
6-Hydroxyhexanoic acid + NADP → Adipate semialdehyde + NADPH + Hydrogen Iondetails