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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-02-08 17:48:36 UTC

Update Date

2022-03-07 03:18:21 UTC

HMDB ID

HMDB0240745

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4,5-dihydroxyhexanoic acid

Description

4,5-dihydroxyhexanoic acid or DHHA is a water-soluble organic acid. It probably arises from the reaction of succinic semialdehyde with an intermediate in the pyruvate dehydrogenase pathway. DHHA is found in the urine and appears to be a marker for Succinic semialdehyde dehydrogenase (SSADH) deficiency (PMID: 3126356 ). SSADH is a disorder that arises from a defect in gamma-aminobutyric acid catabolism, resulting in the accumulation of gamma-hydroxybutyric acid (GHB), 2,4-dihydroxybutyric acid, adipic acid as well as elevated levels of 4,5-dihydroxyhexanoic acid, and 4,5-dihydroxyhexanoic acid lactone. SSADH causes neurological and cognitive disorders of varying severity (PMID: 3126356 ). Children with SSADH deficiency usually manifest with developmental delay, behavioral symptoms, language dysfunction, seizures, hypotonia, extrapyramidal symptoms, and ataxia (PMID: 32055132 ).

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,5-Dihydroxyhexanoate	Generator
DHHA	HMDB
4,5-dihydroxyhexanoic acid	HMDB

Chemical Formula

C₆H₁₂O₄

Average Molecular Weight

148.158

Monoisotopic Molecular Weight

148.073558866

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(O)C(O)CCC(O)=O

InChI Identifier

InChI=1S/C6H12O4/c1-4(7)5(8)2-3-6(9)10/h4-5,7-8H,2-3H2,1H3,(H,9,10)

InChI Key

FKHCKVQMPWUKCV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
1,2-diol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	127.564	30932474
DeepCCS	[M-H]-	124.461	30932474
DeepCCS	[M-2H]-	160.98	30932474
DeepCCS	[M+Na]+	136.128	30932474
AllCCS	[M+H]+	135.7	32859911
AllCCS	[M+H-H2O]+	131.7	32859911
AllCCS	[M+NH4]+	139.5	32859911
AllCCS	[M+Na]+	140.6	32859911
AllCCS	[M-H]-	130.0	32859911
AllCCS	[M+Na-2H]-	132.2	32859911
AllCCS	[M+HCOO]-	134.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,5-dihydroxyhexanoic acid	CC(O)C(O)CCC(O)=O	2964.2	Standard polar	33892256
4,5-dihydroxyhexanoic acid	CC(O)C(O)CCC(O)=O	1247.0	Standard non polar	33892256
4,5-dihydroxyhexanoic acid	CC(O)C(O)CCC(O)=O	1374.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,5-dihydroxyhexanoic acid,1TMS,isomer #1	CC(O[Si](C)(C)C)C(O)CCC(=O)O	1464.8	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,1TMS,isomer #2	CC(O)C(CCC(=O)O)O[Si](C)(C)C	1458.0	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,1TMS,isomer #3	CC(O)C(O)CCC(=O)O[Si](C)(C)C	1438.7	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,2TMS,isomer #1	CC(O[Si](C)(C)C)C(CCC(=O)O)O[Si](C)(C)C	1520.1	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,2TMS,isomer #2	CC(O[Si](C)(C)C)C(O)CCC(=O)O[Si](C)(C)C	1490.5	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,2TMS,isomer #3	CC(O)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1490.3	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,3TMS,isomer #1	CC(O[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1548.6	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(O)CCC(=O)O	1700.1	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,1TBDMS,isomer #2	CC(O)C(CCC(=O)O)O[Si](C)(C)C(C)(C)C	1697.8	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,1TBDMS,isomer #3	CC(O)C(O)CCC(=O)O[Si](C)(C)C(C)(C)C	1669.5	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(CCC(=O)O)O[Si](C)(C)C(C)(C)C	1978.6	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,2TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)C(O)CCC(=O)O[Si](C)(C)C(C)(C)C	1933.4	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,2TBDMS,isomer #3	CC(O)C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1924.5	Semi standard non polar	33892256
4,5-dihydroxyhexanoic acid,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2178.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-dihydroxyhexanoic acid 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 - 4,5-dihydroxyhexanoic acid 10V, Positive-QTOF	splash10-0il0-2900000000-5a18b3c0d41b1557595d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-dihydroxyhexanoic acid 20V, Positive-QTOF	splash10-0c09-9200000000-f07534609c20d1a95bdb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-dihydroxyhexanoic acid 40V, Positive-QTOF	splash10-0a4s-9000000000-c13494d4632afb8a6930	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-dihydroxyhexanoic acid 10V, Negative-QTOF	splash10-0fbj-2900000000-2ffb8fe6cad14c0a26cb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-dihydroxyhexanoic acid 20V, Negative-QTOF	splash10-052f-9100000000-41eab5a1bcf59df274db	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-dihydroxyhexanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-32a4b40d01c386f6acef	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

60645551

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57417380

PDB ID

Not Available

ChEBI ID

Not Available

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

Brown GK, Cromby CH, Manning NJ, Pollitt RJ: Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation. J Inherit Metab Dis. 1987;10(4):367-75. [PubMed:3126356 ]
Yoganathan S, Arunachal G, Kratz L, Varman M, Thomas M, Sudhakar SV, Oommen SP, Danda S: Metabolic Stroke: A Novel Presentation in a Child with Succinic Semialdehyde Dehydrogenase Deficiency. Ann Indian Acad Neurol. 2020 Jan-Feb;23(1):113-117. doi: 10.4103/aian.AIAN_213_18. [PubMed:32055132 ]

Showing metabocard for 4,5-dihydroxyhexanoic acid (HMDB0240745)

MOL for HMDB0240745 (4,5-dihydroxyhexanoic acid)

3D MOL for HMDB0240745 (4,5-dihydroxyhexanoic acid)

3D SDF for HMDB0240745 (4,5-dihydroxyhexanoic acid)

3D-SDF for HMDB0240745 (4,5-dihydroxyhexanoic acid)

PDB for HMDB0240745 (4,5-dihydroxyhexanoic acid)

3D PDB for HMDB0240745 (4,5-dihydroxyhexanoic acid)

SMILES for HMDB0240745 (4,5-dihydroxyhexanoic acid)

INCHI for HMDB0240745 (4,5-dihydroxyhexanoic acid)

Structure for HMDB0240745 (4,5-dihydroxyhexanoic acid)

3D Structure for HMDB0240745 (4,5-dihydroxyhexanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra