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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:09:09 UTC

Update Date

2023-02-21 17:17:51 UTC

HMDB ID

HMDB0012882

Secondary Accession Numbers

HMDB12882

Metabolite Identification

Common Name

Adipate semialdehyde

Description

Adipate 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Hexanal-6-carboxylic acid	ChEBI
5-Carbohydroxy-1-pentanal	ChEBI
5-Formylvaleric acid	ChEBI
6-Hydroxy caproic acid	ChEBI
Adipic acid monoaldehyde	ChEBI
Adipic acid semialdehyde	ChEBI
Adipic monoaldehyde	ChEBI
Adipic semialdehyde	ChEBI
Hexan-1-one-6-carboxylate	Kegg
6-Oxohexanoate	Kegg
6-Oxohexanoic acid	Kegg
1-Hexanal-6-carboxylate	Generator
5-Formylvalerate	Generator
6-Hydroxy caproate	Generator
Adipate monoaldehyde	Generator
Hexan-1-one-6-carboxylic acid	Generator
Adipate semialdehyde	Generator

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

IUPAC Name

6-oxohexanoic acid

Traditional Name

6-oxohexanoic acid

CAS Registry Number

928-81-4

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 Key

PNPPVRALIYXJBW-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

aldehydic acid (CHEBI:2490 )
omega-oxo fatty acid (CHEBI:2490 )
medium-chain fatty acid (CHEBI:2490 )
6-oxo monocarboxylic acid (CHEBI:2490 )
straight-chain fatty acid (CHEBI:2490 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0012882)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012882)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012882)

Source

Endogenous

Endogenous (HMDB: HMDB0012882)

Animal

Animal (HMDB: HMDB0012882)

Exogenous

Food

Food (HMDB: HMDB0012882)

Exogenous (HMDB: HMDB0012882)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012882)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012882)

Lipid metabolism pathway (HMDB: HMDB0012882)

Cellular process

Cell signaling (HMDB: HMDB0012882)

Biochemical process

Lipid transport (HMDB: HMDB0012882)

Role

Biological role

Energy source (HMDB: HMDB0012882)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012882)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	29.8 g/L	ALOGPS
logP	0.42	ALOGPS
logP	0.33	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	31.81 m³·mol⁻¹	ChemAxon
Polarizability	13.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.161	31661259
DarkChem	[M-H]-	123.313	31661259
DeepCCS	[M+H]+	129.976	30932474
DeepCCS	[M-H]-	127.758	30932474
DeepCCS	[M-2H]-	163.603	30932474
DeepCCS	[M+Na]+	138.578	30932474
AllCCS	[M+H]+	130.1	32859911
AllCCS	[M+H-H2O]+	126.0	32859911
AllCCS	[M+NH4]+	133.9	32859911
AllCCS	[M+Na]+	135.0	32859911
AllCCS	[M-H]-	129.2	32859911
AllCCS	[M+Na-2H]-	131.8	32859911
AllCCS	[M+HCOO]-	134.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.65 minutes	32390414
Predicted by Siyang on May 30, 2022	9.471 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.49 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	76.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1256.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	114.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	204.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	127.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	307.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	370.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	114.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	760.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	279.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	938.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	251.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	542.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	284.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	246.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Adipate semialdehyde	OC(=O)CCCCC=O	2242.5	Standard polar	33892256
Adipate semialdehyde	OC(=O)CCCCC=O	1026.3	Standard non polar	33892256
Adipate semialdehyde	OC(=O)CCCCC=O	1184.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Adipate semialdehyde,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCC=O	1279.0	Semi standard non polar	33892256
Adipate semialdehyde,1TMS,isomer #2	C[Si](C)(C)OC=CCCCC(=O)O	1400.7	Semi standard non polar	33892256
Adipate semialdehyde,2TMS,isomer #1	C[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C	1465.9	Semi standard non polar	33892256
Adipate semialdehyde,2TMS,isomer #1	C[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C	1439.5	Standard non polar	33892256
Adipate semialdehyde,2TMS,isomer #1	C[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C	1528.5	Standard polar	33892256
Adipate semialdehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC=O	1519.2	Semi standard non polar	33892256
Adipate semialdehyde,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CCCCC(=O)O	1652.8	Semi standard non polar	33892256
Adipate semialdehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C(C)(C)C	1882.5	Semi standard non polar	33892256
Adipate semialdehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C(C)(C)C	1878.1	Standard non polar	33892256
Adipate semialdehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCCCC(=O)O[Si](C)(C)C(C)(C)C	1789.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Adipate semialdehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aru-9100000000-2e4ea40055a35c1a39c7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adipate semialdehyde GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9600000000-f6045459ae7ea2c05e1a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adipate semialdehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adipate semialdehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 10V, Positive-QTOF	splash10-03di-2900000000-e4846c918bd86e8ad81d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 20V, Positive-QTOF	splash10-03dr-9500000000-96dbf4ca779b71f9a84b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 40V, Positive-QTOF	splash10-0006-9000000000-4c6838822f8b78f24b69	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 10V, Negative-QTOF	splash10-004i-1900000000-42b217c60c3cfe90285b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 20V, Negative-QTOF	splash10-01t9-4900000000-ee529e88593da368017e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 40V, Negative-QTOF	splash10-0006-9000000000-675d5ad3419d73c75c55	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 10V, Positive-QTOF	splash10-01p9-9200000000-2041a85784934bc9906d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 20V, Positive-QTOF	splash10-05mo-9000000000-65b8e816b104e8e2ba34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 40V, Positive-QTOF	splash10-0006-9000000000-3b3a65665b8b5df242d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 10V, Negative-QTOF	splash10-01t9-1900000000-1177328a289f7bb58819	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 20V, Negative-QTOF	splash10-03el-9600000000-b4261ddef35b4c94899e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Adipate semialdehyde 40V, Negative-QTOF	splash10-0006-9000000000-c0aee2e627df9f8d2be4	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029197

KNApSAcK ID

Not Available

Chemspider ID

389748

KEGG Compound ID

C06102

BioCyc ID

6-OXO-HEXANOATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440918

PDB ID

Not Available

ChEBI ID

2490

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Alcohol dehydrogenase [NADP(+)]

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 Ion	details

Showing metabocard for Adipate semialdehyde (HMDB0012882)

MOL for HMDB0012882 (Adipate semialdehyde)

3D MOL for HMDB0012882 (Adipate semialdehyde)

3D SDF for HMDB0012882 (Adipate semialdehyde)

3D-SDF for HMDB0012882 (Adipate semialdehyde)

PDB for HMDB0012882 (Adipate semialdehyde)

3D PDB for HMDB0012882 (Adipate semialdehyde)

SMILES for HMDB0012882 (Adipate semialdehyde)

INCHI for HMDB0012882 (Adipate semialdehyde)

Structure for HMDB0012882 (Adipate semialdehyde)

3D Structure for HMDB0012882 (Adipate semialdehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions