Livestock Metabolome Database: Showing metabocard for 3-Hydroxyisovaleric acid (LMDB00238)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:24 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00238

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Hydroxyisovaleric acid

Description

3-Hydroxyisovaleric acid is a normal animal metabolite excreted in the urine. Elevated levels of this compound are found in several inherited disorders such as Dihydrolipoamide dehydrogenase Deficiency, 3-Methylcrotonyl-CoA carboxylase 1 deficiency, 3-Hydroxy-3-methylglutaryl-CoA lyase deficiency (3-hydroxy-3-methylglutaryl -CoA lyase Deficiency, Biotinidase deficiency multiple carboxylase deficiency late-onset , Late onset multiple carboxylase deficiency, HolMcarboxylase synthetase deficiency, 3-Methylcrotonyl-CoA carboxylase 2 deficiency. 3-Hydroxyisovaleric acid is also elevated in smokers, in subjects undergoing long-term anticonvulsant therapy with carbamazepine and/or phenytoin. These levels are elevated due to impairment of renal reclamation of biotin. Levels may also be increased from prolonged consumption of raw egg-whites (PMID: 16895887 , 9523856 , 15447901 , 9176832 )(OMIM: 210210 , 253270 , 600529 , 253260 , 246450 , 210200 , 238331 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-3-methylbutyric acid	ChEBI
3-Hydroxy-isovaleric acid	ChEBI
3-Methyl-3-hydroxybutyric acid	ChEBI
3-OH-Isovaleric acid	ChEBI
beta-Hydroxy-beta-methylbutyric acid	ChEBI
beta-Hydroxyisovaleric acid	ChEBI
HMB	ChEBI
HMB-D6	ChEBI
3-Hydroxy-3-methylbutyrate	Generator
3-Hydroxy-isovalerate	Generator
3-Methyl-3-hydroxybutyrate	Generator
3-OH-Isovalerate	Generator
b-Hydroxy-b-methylbutyrate	Generator
b-Hydroxy-b-methylbutyric acid	Generator
beta-Hydroxy-beta-methylbutyrate	Generator
Β-hydroxy-β-methylbutyrate	Generator
Β-hydroxy-β-methylbutyric acid	Generator
b-Hydroxyisovalerate	Generator
b-Hydroxyisovaleric acid	Generator
beta-Hydroxyisovalerate	Generator
Β-hydroxyisovalerate	Generator
Β-hydroxyisovaleric acid	Generator
3-Hydroxyisovalerate	Generator
beta Hydroxy beta methylbutyrate	HMDB
beta-Hydroxy beta-methylbutyrate	HMDB
3-Hydroxy-3-methyl-butanoate	HMDB
3-Hydroxy-3-methyl-butanoic acid	HMDB
3-Hydroxy-3-methyl-butyric acid	HMDB
3-Hydroxy-3-methylbutanoate	HMDB
3-Hydroxy-3-methylbutanoic acid	HMDB
3-Hydroxyisovaleric acid	MeSH

Chemical Formula

C₅H₁₀O₃

Average Molecular Weight

118.1311

Monoisotopic Molecular Weight

118.062994186

IUPAC Name

3-hydroxy-3-methylbutanoic acid

Traditional Name

3-hydroxyisovaleric acid

CAS Registry Number

625-08-1

SMILES

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

InChI Identifier

InChI=1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7)

InChI Key

AXFYFNCPONWUHW-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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-hydroxy monocarboxylic acid (CHEBI:37084 )
Hydroxy fatty acids (LMFA01050396 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.12	ALOGPS
logP	-0.11	ChemAxon
logS	0.51	ALOGPS
pKa (Strongest Acidic)	4.55	ChemAxon
pKa (Strongest Basic)	-2.7	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	2	ChemAxon
Refractivity	28.1 m³·mol⁻¹	ChemAxon
Polarizability	11.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000t-0900000000-56f9e1ee9e19bacfc939	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-0900000000-56f9e1ee9e19bacfc939	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100000000-0809a885d114ba6b21d7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0089-6910000000-3573bf97996ef7107955	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-9000000000-1381eacc487b12932a43	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00dj-9000000000-f10c5afd9954f294ea91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-9600000000-3b24b27c64b89a6a5b25	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-9300000000-e715db06e575104deccd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-885e3d959712c9998250	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0avi-9800000000-f0296f537bd22b26f173	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014i-1900000000-b947237de42eec92a67e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-9400000000-13e4ec512c0fde3123ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05tb-9200000000-96c7d7b3f54e7377a875	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aba-9000000000-3cc71227974213e131c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-9400000000-9721ad435e43092a072d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-13f5bd4a628f51aec810	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-0eeab2c474971ae60e7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-5900000000-2f664d0b967c87e7358c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zn9-9500000000-233e5cd462b504c09d3c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-62361f03b7c7a0d82bc4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-8900000000-a25104a0136877edd57e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-d2d6bcff64e0a706fc95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-65f5183bc669daba34f4	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9000000000-c15a37ad10e6379350aa	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details
Serum	Detected and Quantified	8.5965 +/- 6.8898 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.0857 +/- 1.1652 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.7759 +/- 0.9691 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.4023 +/- 3.7789 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.9977 +/- 4.5921 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.0658 +/- 1.2936 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.82 +/- 0.31 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	6.0913 +/- 4.8179 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.4741 +/- 1.6903 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.8055 +/- 0.741 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.7164 +/- 0.76 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.9216 +/- 4.5478 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.9443 +/- 1.5193 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.0484 +/- 1.1858 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.9977 +/- 0.9823 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.469 +/- 3.2718 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.81 +/- 3.6301 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.8389 +/- 0.8452 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.819 +/- 2.8037 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.5219 +/- 0.0595 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.7286 +/- 2.3291 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000754

FooDB ID

FDB022225

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5722

PDB ID

Not Available

Wikipedia Link

Beta-Hydroxy_beta-methylbutyric_acid

Chemspider ID

62571

ChEBI ID

37084

PubChem Compound ID

69362

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Stratton SL, Bogusiewicz A, Mock MM, Mock NI, Wells AM, Mock DM: Lymphocyte propionyl-CoA carboxylase and its activation by biotin are sensitive indicators of marginal biotin deficiency in humans. Am J Clin Nutr. 2006 Aug;84(2):384-8. [16895887 ]
Mock DM, Mock NI, Nelson RP, Lombard KA: Disturbances in biotin metabolism in children undergoing long-term anticonvulsant therapy. J Pediatr Gastroenterol Nutr. 1998 Mar;26(3):245-50. [9523856 ]
Sealey WM, Teague AM, Stratton SL, Mock DM: Smoking accelerates biotin catabolism in women. Am J Clin Nutr. 2004 Oct;80(4):932-5. [15447901 ]
Mock DM, Stadler DD: Conflicting indicators of biotin status from a cross-sectional study of normal pregnancy. J Am Coll Nutr. 1997 Jun;16(3):252-7. [9176832 ]

Showing metabocard for 3-Hydroxyisovaleric acid (LMDB00238)

Structure for LMDB00238 (3-Hydroxyisovaleric acid)