MiMeDB: Showing metabocard for 2-Hydroxybutyric acid (MMDBc0000813)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 22:03:36 UTC

Update Date

2024-04-30 19:33:44 UTC

Metabolite ID

MMDBc0000813

Metabolite Identification

Common Name

2-Hydroxybutyric acid

Description

2-Hydroxybutyric acid (CAS: 600-15-7), also known as alpha-hydroxybutyrate, is an organic acid derived from alpha-ketobutyrate. alpha-Ketobutyrate is produced by amino acid catabolism (threonine and methionine) and glutathione anabolism (cysteine formation pathway) and is metabolized into propionyl-CoA and carbon dioxide (PMID: 20526369 ). 2-Hydroxybutyric acid is formed as a byproduct from the formation of alpha-ketobutyrate via a reaction catalyzed by lactate dehydrogenase (LDH) or alpha-hydroxybutyrate dehydrogenase (alphaHBDH). alpha-Hydroxybutyric acid is primarily produced in mammalian hepatic tissues that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification of xenobiotics in the liver can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway (which forms methionine) into the transsulfuration pathway (which forms cystathionine). alpha-Ketobutyrate is released as a byproduct when cystathionine is cleaved into cysteine that is incorporated into glutathione. Chronic shifts in the rate of glutathione synthesis may be reflected by urinary excretion of 2-hydroxybutyrate. 2-Hydroxybutyrate is an early marker for both insulin resistance and impaired glucose regulation that appears to arise due to increased lipid oxidation and oxidative stress (PMID: 20526369 ). 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.g. birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as "cerebral" lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for early-stage type II diabetes (PMID: 19166731 ). It was concluded from studies done in the mid-1970s that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydroxybutyric acid (PMID: 168632 ).

Structure

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


  Mrv1652309142106383D          

 15 14  0  0  0  0            999 V2000
   -2.0817    0.1757    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8778   -0.0846   -0.6959 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3603   -0.2117    0.1873 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5730    0.9558    0.9144 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5707   -0.4592   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903   -1.4832   -1.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722    0.3608   -0.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322    0.4420    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329   -0.7417    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    0.9886   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6923    0.7513   -1.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154   -1.0471   -1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2243   -1.0352    0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733    1.3514    0.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5053    0.0372   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  8  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  1  0  0  0
  4 14  1  0  0  0  0
  7 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000813

> <DATABASE_NAME>
MIME

> <SMILES>
[H]OC(=O)[C@@]([H])(O[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1

> <INCHI_KEY>
AFENDNXGAFYKQO-VKHMYHEASA-N

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.105

> <EXACT_MASS>
104.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.984831454501116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-hydroxybutanoic acid

> <ALOGPS_LOGP>
-0.16

> <JCHEM_LOGP>
0.050692876999999914

> <ALOGPS_LOGS>
0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.293154365104638

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.989998858113875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7935876935907205

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
23.3638

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.84e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-2-hydroxybutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.082   0.176   0.171  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.878  -0.085  -0.696  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.360  -0.212   0.187  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.573   0.956   0.914  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.571  -0.459  -0.632  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.590  -1.483  -1.379  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.672   0.361  -0.626  0.00  0.00           O+0
HETATM    8  H   UNK     0      -1.832   0.442   1.207  0.00  0.00           H+0
HETATM    9  H   UNK     0      -2.733  -0.742   0.238  0.00  0.00           H+0
HETATM   10  H   UNK     0      -2.737   0.989  -0.237  0.00  0.00           H+0
HETATM   11  H   UNK     0      -0.692   0.751  -1.414  0.00  0.00           H+0
HETATM   12  H   UNK     0      -1.015  -1.047  -1.223  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.224  -1.035   0.915  0.00  0.00           H+0
HETATM   14  H   UNK     0       1.473   1.351   0.731  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.505   0.037  -0.160  0.00  0.00           H+0
CONECT    1    2    8    9   10                                             
CONECT    2    1    3   11   12                                             
CONECT    3    2    4    5   13                                             
CONECT    4    3   14                                                       
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5   15                                                       
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10    1                                                            
CONECT   11    2                                                            
CONECT   12    2                                                            
CONECT   13    3                                                            
CONECT   14    4                                                            
CONECT   15    7                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

Synonyms

Value	Source
(S)-2-Hydroxybutanoic acid	ChEBI
2-Hydroxybutyrate	ChEBI
2-Hydroxybutyric acid	ChEBI
L-2-Hydroxybutanoic acid	ChEBI
L-2-Hydroxybutyric acid	ChEBI
L-alpha-Hydroxybutanoic acid	ChEBI
L-alpha-Hydroxybutyric acid	ChEBI
(S)-2-Hydroxybutanoate	Generator
L-2-Hydroxybutanoate	Generator
L-2-Hydroxybutyrate	Generator
L-a-Hydroxybutanoate	Generator
L-a-Hydroxybutanoic acid	Generator
L-alpha-Hydroxybutanoate	Generator
L-Α-hydroxybutanoate	Generator
L-Α-hydroxybutanoic acid	Generator
L-a-Hydroxybutyrate	Generator
L-a-Hydroxybutyric acid	Generator
L-alpha-Hydroxybutyrate	Generator
L-Α-hydroxybutyrate	Generator
L-Α-hydroxybutyric acid	Generator
(S)-2-Hydroxybutyrate	Generator
2-Hydroxybutanoate	Generator
(+)-2-Hydroxy-n-butyric acid	HMDB
(+)-2-Hydroxybutanoic acid	HMDB
(+)-2-Hydroxybutyric acid	HMDB
(+)-alpha-Hydroxybutyric acid	HMDB
(+)-α-Hydroxybutyric acid	HMDB
(2S)-2-Hydroxybutanoic acid	HMDB
(S)-(+)-2-Hydroxybutanoic acid	HMDB
(S)-2-Hydroxybutyric acid	HMDB
2-Hydroxybutanoic acid	HMDB
alpha-Hydroxy-n-butyric acid	HMDB
alpha-Hydroxybutanoic acid	HMDB
alpha-Hydroxybutyric acid	HMDB
α-Hydroxy-n-butyric acid	HMDB
α-Hydroxybutanoic acid	HMDB
α-Hydroxybutyric acid	HMDB

Molecular Formula

C₄H₈O₃

Average Mass

104.105

Monoisotopic Mass

104.047344118

IUPAC Name

(2S)-2-hydroxybutanoic acid

Traditional Name

(S)-2-hydroxybutyric acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]([H])(O[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1

InChI Key

AFENDNXGAFYKQO-VKHMYHEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Fatty acid
Alpha-hydroxy acid
Secondary 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

2-hydroxybutyric acid (CHEBI:50613 )
Hydroxy fatty acids (C05984 )
Hydroxy fatty acids (LMFA01050342 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	484 g/L	ALOGPS
logP	-0.16	ALOGPS
logP	0.051	ChemAxon
logS	0.67	ALOGPS
pKa (Strongest Acidic)	3.99	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	2	ChemAxon
Refractivity	23.36 m³·mol⁻¹	ChemAxon
Polarizability	9.98 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 (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001j-0900000000-44dd1bf8072e5731bac4	2020-02-05	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00e9-9700000000-93eba027d5343e3d6ce1	2020-02-05	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-1910000000-3bc9898b26df33cad244	2020-02-05	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-4d935da8e593ec61fd96	2020-02-05	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-0900000000-44dd1bf8072e5731bac4	2020-02-05	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00e9-9700000000-93eba027d5343e3d6ce1	2020-02-05	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-1910000000-3bc9898b26df33cad244	2020-02-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-9600000000-f688c3e6fdeb5f0270c5	2020-02-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4j-9200000000-e3b371c29b9ebed3199b	2020-02-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfs-9700000000-bccfada2c97e04d34417	2020-02-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-9000000000-4d935da8e593ec61fd96	2020-02-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-2900000000-3c7915ea71886873f024	2020-02-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0zfr-7900000000-d91c840306a06d4ea513	2020-02-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-94eb4d9d668d4d53231b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-9500000000-a90d8674aafbec41b8b2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9400000000-7b0a49d8800ded4cdff4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0zfr-7900000000-52227d0dd814179fde45	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0zmi-9600000000-8ea58ec01176ecce4735	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-9400000000-7bdf5cb6c5aa8c1d607d	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-bf04b472392c16bd165c	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-483980f183cd4095b2f3	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-9185cef9251e02ac688c	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9200000000-ea836921fe44635e66c2	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-cf8130e8094c63aa0e25	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052o-9000000000-d175dd460cd717e71350	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-0244ee6a1375f83df3a2	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a4c46731c8286baabca9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-d938708d3f7f8d712710	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ap0-9100000000-a0763e4b908fc98b5853	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9077c11ebfee5a552d35	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2020-02-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		2020-02-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-14	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2020-02-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Prostate
Saliva
Sweat
Urine

Tissue Locations

Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191728	Dihydrolipoyl dehydrogenase, mitochondrial	Unknown	P09622	Homo sapiens
MMDBp0192023	Sulfotransferase family cytosolic 2B member 1	Enzyme	O00204	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192511	L-lactate dehydrogenase A-like 6A	Unknown	Q6ZMR3	Homo sapiens
MMDBp0193918	L-lactate dehydrogenase B chain	Unknown	P07195	Homo sapiens
MMDBp0193919	L-lactate dehydrogenase C chain	Unknown	P07864	Homo sapiens
MMDBp0193920	L-lactate dehydrogenase A chain	Unknown	P00338	Homo sapiens
MMDBp0193921	L-lactate dehydrogenase A-like 6B	Unknown	Q9BYZ2	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000041	2-Hydroxybutyric acid	2-Ketobutyric acid	lactate dehydrogenase A		VMH; KEGG	10108 21765

Health Effects and Bioactivity

Health Outcome/Bioactivity	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease	Association	Human Saliva	HMDB	23857558
Frontotemporal dementia	Association	Human Saliva	HMDB	23857558
Eosinophilic esophagitis	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	72	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	5	Human appendix biopsy; Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Firmicutes	199	Human stool; Human ; Human supragingival plaque; Human saliva; Human feces; Human urine; Human sputum; Human subgingival plaque; Human vaginal fluid; Human mucosa; Pig ; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Archaea	Euryarchaeota	2	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	88	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	2	Human feces; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
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 Feces	Detected but not Quantified									HMDB
Human Saliva	Detected and Quantified	7.26	4.47			uM	Adult (>18 years old)	Male	Alzheimer's disease	HMDB	23857558
Human Urine	Detected and Quantified	248.732				umol/mmol creatinine	Infant (0-1 year old)	Male	Dihydrolipoamide Dehydrogenase Deficiency	HMDB	6688766
Human Blood	Detected and Quantified	21.4	5.6			uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Saliva	Detected and Quantified	7.30	1.32			uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	HMDB	23857558
Human Blood	Detected and Quantified	28.0	14.4			uM	Adult (>18 years old)	Female	Late-onset preeclampsia	HMDB	23159745
Human Saliva	Detected and Quantified	8.12	5.32			uM	Adult (>18 years old)	Both	Lewy body disease	HMDB	23857558
Human Blood	Detected and Quantified	15.0	7.4			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23313728
Human Blood	Detected and Quantified	16.69	6.25			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Blood	Detected and Quantified	16.93	8.17			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23535240
Human Blood	Detected and Quantified	19.5	7.4			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Blood	Detected and Quantified	21.2	7.5			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23159745
Human Cerebrospinal fluid (csf)	Detected and Quantified	85				uM	Adult (>18 years old)	Both	Normal	HMDB	18502700
Human Urine	Detected and Quantified			0	3	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	6.0	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	6.1	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	9.3	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0.26	0.53	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.31	0.69	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Saliva	Detected and Quantified	10.42	9.20			uM	Adult (>18 years old)	Female	Normal	HMDB	23857558
Human Urine	Detected and Quantified	2.445		0	4.89	umol/mmol creatinine	Not Specified	Both	Normal	HMDB	168632
Human Urine	Detected and Quantified	2.8		1.2	6.9	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	26.9	32.92			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Cerebrospinal fluid (csf)	Detected and Quantified	35.0	24.0			uM	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human Cerebrospinal fluid (csf)	Detected and Quantified	37 +/- 21		10	76	uM	Children (1-13 years old)	Both	Normal	HMDB	8376520
Human Cerebrospinal fluid (csf)	Detected and Quantified	40.0	24.0			uM	Adult (>18 years old)	Both	Normal	HMDB	18502700
Human Blood	Detected and Quantified	54.0		8.0	80.0	uM	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human Blood	Detected and Quantified			8.00	80.0	uM	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human Urine	Detected and Quantified	8.699	10.366			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	>25.0				umol/mmol creatinine	Adult (>18 years old)	Both	Pyruvate dehydrogenase deficiency	HMDB	OMIM 238331
Human Urine	Detected and Quantified	3.29	3.529			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.0		0.0	10.0	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified			8.00	80.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22024767
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22024767
Human Sweat	Detected but not Quantified						Adult	Both	Normal	HMDB	26755145
Human Blood	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	27355821
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000008

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021867

KNApSAcK ID

Not Available

Chemspider ID

389701

KEGG Compound ID

C05984

BioCyc ID

CPD-3564

BiGG ID

Not Available

Wikipedia Link

2-Hydroxybutyric_acid

METLIN ID

Not Available

PubChem Compound

440864

PDB ID

Not Available

ChEBI ID

50613

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Landaas S, Pettersen JE: Clinical conditions associated with urinary excretion of 2-hydroxybutyric acid. Scand J Clin Lab Invest. 1975 May;35(3):259-66. [PubMed:168632 ]
Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. doi: 10.1016/0731-7085(93)80171-v. [PubMed:8257730 ]
Li X, Xu Z, Lu X, Yang X, Yin P, Kong H, Yu Y, Xu G: Comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry for metabonomics: Biomarker discovery for diabetes mellitus. Anal Chim Acta. 2009 Feb 9;633(2):257-62. doi: 10.1016/j.aca.2008.11.058. Epub 2008 Dec 3. [PubMed:19166731 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Gall WE, Beebe K, Lawton KA, Adam KP, Mitchell MW, Nakhle PJ, Ryals JA, Milburn MV, Nannipieri M, Camastra S, Natali A, Ferrannini E: alpha-hydroxybutyrate is an early biomarker of insulin resistance and glucose intolerance in a nondiabetic population. PLoS One. 2010 May 28;5(5):e10883. doi: 10.1371/journal.pone.0010883. [PubMed:20526369 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Charles J. Pouchert (1992). Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 854B. Aldrich Chemical.
Charles J. Pouchert (1985). Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 548D. Aldrich Chemical Company.
H. Keith Chenault, Mahn Joo Kim, Alan Akiyama, Toshifumi Miyazawa, Ethan S. Simon, and George M. Whitesides (1987). Chenault, H.K. et al., J.O.C., 1987, 52, 2608. J. Org. Chem..
Duvillier, E., Ann. (1897). Duvillier, E., Ann. Chim. Phys., 1879, 17, 532. Chim. Phys..
Horn, D.H.S. (1954). Horn, D.H.S. et al., J.C.S., 1954, 1460. J.C.S..
Levene, P.A. et al. (1941). Levene, P.A. et al., J. Biol. Chem., 1941, 141, 391. J. Biol. Chem..
Mori, K. et al. (1979). Mori, K. et al., Tetrahedron, 1979, 35, 1601. Tetrahedron.
Wong, C.H. et al. (1985). Wong, C.H. et al., J.O.C., 1985, 50, 1992. J.O.C..

Showing metabocard for 2-Hydroxybutyric acid (MMDBc0000813)

MOL for #<Metabolite:0x00007fecb403a068>

3D MOL for #<Metabolite:0x00007fecb403a068>

3D SDF for #<Metabolite:0x00007fecb403a068>

3D-SDF for #<Metabolite:0x00007fecb403a068>

PDB for #<Metabolite:0x00007fecb403a068>

3D PDB for #<Metabolite:0x00007fecb403a068>

SMILES for #<Metabolite:0x00007fecb403a068>

INCHI for #<Metabolite:0x00007fecb403a068>

Structure for #<Metabolite:0x00007fecb403a068>

3D Structure for #<Metabolite:0x00007fecb403a068>