MiMeDB: Showing metabocard for 2-Hydroxyvalerate (MMDBc0033543)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:52:55 UTC

Update Date

2024-04-30 20:12:19 UTC

Metabolite ID

MMDBc0033543

Metabolite Identification

Common Name

2-Hydroxyvalerate

Description

2-Hydroxyvaleric acid is an organic acid present in human biofluids. Its presence in urine has been associated with lactic acidosis, which occurs in Succinic Acidemia (OMIM 600335 ), a syndrome of organic acidemia associated with congenital lactic acidosis and decreased NADH-cytochrome c reductase activity. 2-Hydroxyvaleric acid presence associated with lactic acidosis has also been found in Propionyl-CoA carboxylase deficiency (OMIM 253260 ), or Multiple carboxylase deficiency (MCD), an autosomal recessive metabolic disorder characterized primarily by cutaneous and neurologic abnormalities. (PMID: 9389332 , 1790187 , 3378323 , 3383430 , 7313494 ).

Structure

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

Synonyms

Value	Source
alpha-Hydroxy-N-valeric acid	ChEBI
alpha-Hydroxyvaleric acid	ChEBI
a-Hydroxy-N-valerate	Generator
a-Hydroxy-N-valeric acid	Generator
alpha-Hydroxy-N-valerate	Generator
Α-hydroxy-N-valerate	Generator
Α-hydroxy-N-valeric acid	Generator
a-Hydroxyvalerate	Generator
a-Hydroxyvaleric acid	Generator
alpha-Hydroxyvalerate	Generator
Α-hydroxyvalerate	Generator
Α-hydroxyvaleric acid	Generator
2-Hydroxyvalerate	Generator
(+-)-2-Hydroxypentanoate	HMDB
(+-)-2-Hydroxypentanoic acid	HMDB
(S)-2-Hydroxyvaleric acid	HMDB
2-Hydroxy-pentanoate	HMDB
2-Hydroxy-pentanoic acid	HMDB
2-Hydroxypentanoate	HMDB
2-Hydroxypentanoic acid	HMDB
DL-2-Hydroxy valeric acid	HMDB
DL-2-Hydroxy valerate	HMDB
2-Hydroxyvaleric acid	ChEBI

Molecular Formula

C₅H₁₀O₃

Average Mass

118.1311

Monoisotopic Mass

118.062994186

IUPAC Name

2-hydroxypentanoic acid

Traditional Name

pentanoic acid, 2-hydroxy-

CAS Registry Number

617-31-2

SMILES

CCCC(O)C(O)=O

InChI Identifier

InChI=1S/C5H10O3/c1-2-3-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)

InChI Key

JRHWHSJDIILJAT-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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxy monocarboxylic acid (CHEBI:60647 )
Hydroxy fatty acids (LMFA01050007 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	204 g/L	ALOGPS
logP	0.26	ALOGPS
logP	0.5	ChemAxon
logS	0.24	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	27.96 m³·mol⁻¹	ChemAxon
Polarizability	11.83 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-1900000000-d70300be52196291976d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-1900000000-d70300be52196291976d	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bc-9000000000-8ef25031872550bc4b5a	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00g1-9520000000-c9d4fd57ae20696954b7	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-01b9-5900000000-01385a49616d72e0af48	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-5900000000-3d71ffe5b1c985dfc9cc	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fdo-9200000000-659ff4c4697dba592584	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-96838793607ef6f63efe	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-5900000000-a4fc27ef3911175a0401	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9200000000-59dd4da8ca2bf68da3f1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9000000000-bc0895fffaa6399f624b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-4900000000-2614517a07efec2cf55f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-9300000000-a44dada0b4de6fdaa3d5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e3ae3abd89704d8b4660	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9100000000-97bcc465197c4cce0de9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-2cfc42755749c6d13ccc	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-5b66cfecc9e0301583d4	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192023	Sulfotransferase family cytosolic 2B member 1	Enzyme	O00204	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified			0	4	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	31506554
Human Urine	Detected and Quantified	0.1	0.1			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	1790187
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Blood	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0001863

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022717

KNApSAcK ID

Not Available

Chemspider ID

88482

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98009

PDB ID

Not Available

ChEBI ID

60647

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Jellum E, Harboe M, Bjune G, Wold S: Interpreting complicated chromatographic patterns. J Pharm Biomed Anal. 1991;9(8):663-9. doi: 10.1016/0731-7085(91)80193-d. [PubMed:1790187 ]
Verhaeghe BJ, Lefevere MF, De Leenheer AP: Solid-phase extraction with strong anion-exchange columns for selective isolation and concentration of urinary organic acids. Clin Chem. 1988 Jun;34(6):1077-83. [PubMed:3378323 ]
Asano K, Miyamoto I, Matsushita T, Murakami Y, Minoura S, Wagatsuma T, Oshima M: Succinic acidemia: a new syndrome of organic acidemia associated with congenital lactic acidosis and decreased NADH-cytochrome c reductase activity. Clin Chim Acta. 1988 Apr 29;173(3):305-12. doi: 10.1016/0009-8981(88)90018-6. [PubMed:3383430 ]
Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. doi: 10.3109/00365518109092023. [PubMed:7313494 ]
Kim KR, Kim JH, Jeong DH, Paek DJ, Liebich HM: Gas chromatographic profiling analysis of urinary organic acids from nonsmokers and smokers. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):1-8. doi: 10.1016/s0378-4347(97)00358-7. [PubMed:9389332 ]

Showing metabocard for 2-Hydroxyvalerate (MMDBc0033543)

MOL for #<Metabolite:0x00007f46dc2df490>

3D MOL for #<Metabolite:0x00007f46dc2df490>

3D SDF for #<Metabolite:0x00007f46dc2df490>

3D-SDF for #<Metabolite:0x00007f46dc2df490>

PDB for #<Metabolite:0x00007f46dc2df490>

3D PDB for #<Metabolite:0x00007f46dc2df490>

SMILES for #<Metabolite:0x00007f46dc2df490>

INCHI for #<Metabolite:0x00007f46dc2df490>

Structure for #<Metabolite:0x00007f46dc2df490>

3D Structure for #<Metabolite:0x00007f46dc2df490>