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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 18:35:06 UTC

HMDB ID

HMDB0000421

Secondary Accession Numbers

HMDB00421

Metabolite Identification

Common Name

2,3-Dihydroxyvaleric acid

Description

2,3-Dihydroxyvaleric acid (DHVA) belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. This compound has been detected in extracts from the purple carrot (https://doi.org/10.3390/app10238493). It is likely a hydroxylation derivative of the more common 2-hydroxyvaleric acid (an algal metabolite derived from a valeric acid) or 3-hydroxyvaleric acid (a 5-carbon ketone body made from odd carbon fatty acids in the liver). Very little is known about the origin of this particular hydroxy fatty acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Dihydroxyvalerate	Generator
2,3-Dihydroxy-valerate	HMDB
2,3-Dihydroxy-valeric acid	HMDB

Chemical Formula

C₅H₁₀O₄

Average Molecular Weight

134.1305

Monoisotopic Molecular Weight

134.057908808

IUPAC Name

2,3-dihydroxypentanoic acid

Traditional Name

2,3-dihydroxyvaleric acid

CAS Registry Number

26386-47-0

SMILES

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

InChI Identifier

InChI=1S/C5H10O4/c1-2-3(6)4(7)5(8)9/h3-4,6-7H,2H2,1H3,(H,8,9)

InChI Key

CJXCLBPFKGZXJP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Beta-hydroxy acid
Branched fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Methyl-branched fatty acid
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Hydroxy fatty acids (LMFA01050384 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0000421)
Adiposome (HMDB: HMDB0000421)

Biofluid or Excreta

Urine (HMDB: HMDB0000421)

Cellular substructure

Cytoplasm (HMDB: HMDB0000421)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000421)

Source

Endogenous

Endogenous (HMDB: HMDB0000421)

Animal

Animal (HMDB: HMDB0000421)

Exogenous

Food

Food (HMDB: HMDB0000421)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000421)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000421)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000421)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000421)

Nutrient

Nutrient (HMDB: HMDB0000421)

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	349 g/L	ALOGPS
logP	-0.87	ALOGPS
logP	-0.58	ChemAxon
logS	0.42	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	29.33 m³·mol⁻¹	ChemAxon
Polarizability	12.72 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]+	128.28	31661259
DarkChem	[M-H]-	124.723	31661259
AllCCS	[M+H]+	133.392	32859911
AllCCS	[M-H]-	125.304	32859911
DeepCCS	[M+H]+	126.478	30932474
DeepCCS	[M-H]-	123.68	30932474
DeepCCS	[M-2H]-	160.242	30932474
DeepCCS	[M+Na]+	135.062	30932474
AllCCS	[M+H]+	133.4	32859911
AllCCS	[M+H-H2O]+	129.2	32859911
AllCCS	[M+NH4]+	137.3	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	125.3	32859911
AllCCS	[M+Na-2H]-	128.0	32859911
AllCCS	[M+HCOO]-	131.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydroxyvaleric acid	CCC(O)C(O)C(O)=O	2532.0	Standard polar	33892256
2,3-Dihydroxyvaleric acid	CCC(O)C(O)C(O)=O	1153.7	Standard non polar	33892256
2,3-Dihydroxyvaleric acid	CCC(O)C(O)C(O)=O	1223.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydroxyvaleric acid,1TMS,isomer #1	CCC(O[Si](C)(C)C)C(O)C(=O)O	1294.5	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,1TMS,isomer #2	CCC(O)C(O[Si](C)(C)C)C(=O)O	1295.0	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,1TMS,isomer #3	CCC(O)C(O)C(=O)O[Si](C)(C)C	1209.9	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,2TMS,isomer #1	CCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)O	1365.7	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,2TMS,isomer #2	CCC(O[Si](C)(C)C)C(O)C(=O)O[Si](C)(C)C	1335.6	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,2TMS,isomer #3	CCC(O)C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1325.9	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,3TMS,isomer #1	CCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1446.9	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,1TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(O)C(=O)O	1535.3	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,1TBDMS,isomer #2	CCC(O)C(O[Si](C)(C)C(C)(C)C)C(=O)O	1522.5	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,1TBDMS,isomer #3	CCC(O)C(O)C(=O)O[Si](C)(C)C(C)(C)C	1451.6	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,2TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)O	1793.5	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,2TBDMS,isomer #2	CCC(O[Si](C)(C)C(C)(C)C)C(O)C(=O)O[Si](C)(C)C(C)(C)C	1773.7	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,2TBDMS,isomer #3	CCC(O)C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1755.2	Semi standard non polar	33892256
2,3-Dihydroxyvaleric acid,3TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2025.3	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 - 2,3-Dihydroxyvaleric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-b99bc2c93850290131e7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (3 TMS) - 70eV, Positive	splash10-00ui-9362000000-96062ff863982365ae7b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydroxyvaleric acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	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 - 2,3-Dihydroxyvaleric acid 10V, Positive-QTOF	splash10-014r-4900000000-20b2edde0c5d3b3d32d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 20V, Positive-QTOF	splash10-01bj-9500000000-547313763284b7681c2a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 40V, Positive-QTOF	splash10-052f-9000000000-290a6c9756c05ec3a4ff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 10V, Negative-QTOF	splash10-001r-9700000000-602eb013dc501439b273	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 20V, Negative-QTOF	splash10-0079-9100000000-68ac46f450791e7517ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 40V, Negative-QTOF	splash10-0ab9-9000000000-1af3b0a3e615f4d38c42	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 10V, Positive-QTOF	splash10-00dr-9300000000-b0218ca64257be6304a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 20V, Positive-QTOF	splash10-0abi-9000000000-663455a2081e72dc3e67	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 40V, Positive-QTOF	splash10-0006-9000000000-35d8d27e74b0336c97f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 10V, Negative-QTOF	splash10-00lr-3900000000-62d32c9d5d5f6fbe7cfe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 20V, Negative-QTOF	splash10-0a6r-9000000000-0691122f3bb8bc566293	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydroxyvaleric acid 40V, Negative-QTOF	splash10-0a4i-9000000000-65d174997cc085a8dc85	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

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

FDB022035

KNApSAcK ID

Not Available

Chemspider ID

13451358

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5410

PubChem Compound

20848966

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

Kogl, Fritz; Duisberg, Herwarth; Erxleben, Hanni. Fungus poisons. I. Muscarine. I. Ann. (1931), 489 156-92.

Material Safety Data Sheet (MSDS)

Not Available

General References

Holmes E, Foxall PJ, Spraul M, Farrant RD, Nicholson JK, Lindon JC: 750 MHz 1H NMR spectroscopy characterisation of the complex metabolic pattern of urine from patients with inborn errors of metabolism: 2-hydroxyglutaric aciduria and maple syrup urine disease. J Pharm Biomed Anal. 1997 Jul;15(11):1647-59. [PubMed:9260660 ]

Showing metabocard for 2,3-Dihydroxyvaleric acid (HMDB0000421)

MOL for HMDB0000421 (2,3-Dihydroxyvaleric acid)

3D MOL for HMDB0000421 (2,3-Dihydroxyvaleric acid)

3D SDF for HMDB0000421 (2,3-Dihydroxyvaleric acid)

3D-SDF for HMDB0000421 (2,3-Dihydroxyvaleric acid)

PDB for HMDB0000421 (2,3-Dihydroxyvaleric acid)

3D PDB for HMDB0000421 (2,3-Dihydroxyvaleric acid)

SMILES for HMDB0000421 (2,3-Dihydroxyvaleric acid)

INCHI for HMDB0000421 (2,3-Dihydroxyvaleric acid)

Structure for HMDB0000421 (2,3-Dihydroxyvaleric acid)

3D Structure for HMDB0000421 (2,3-Dihydroxyvaleric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra