Bovine Metabolome Database: Showing metabocard for 2-Hydroxybutyric acid (BMDB0000008)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:07:18 UTC

Update Date

2020-05-11 22:52:21 UTC

BMDB ID

BMDB0000008

Secondary Accession Numbers

BMDB00008

Metabolite Identification

Common Name

2-Hydroxybutyric acid

Description

2-Hydroxybutyric acid, also known as alpha-hydroxybutyrate or 2-hydroxybutanoate, 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. 2-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 2-Hydroxybutyric acid is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.105

Monoisotopic Molecular Weight

104.047344118

IUPAC Name

(2S)-2-hydroxybutanoic acid

Traditional Name

(S)-2-hydroxybutyric acid

CAS Registry Number

600-15-7

SMILES

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

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 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	44.2 °C	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	-0.16	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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001j-0900000000-44dd1bf8072e5731bac4	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00e9-9700000000-93eba027d5343e3d6ce1	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-1910000000-3bc9898b26df33cad244	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-4d935da8e593ec61fd96	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-0900000000-44dd1bf8072e5731bac4	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00e9-9700000000-93eba027d5343e3d6ce1	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-1910000000-3bc9898b26df33cad244	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-9600000000-f688c3e6fdeb5f0270c5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4j-9200000000-e3b371c29b9ebed3199b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfs-9700000000-bccfada2c97e04d34417	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-9000000000-4d935da8e593ec61fd96	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-2900000000-3c7915ea71886873f024	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0zfr-7900000000-d91c840306a06d4ea513	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-94eb4d9d668d4d53231b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-9500000000-a90d8674aafbec41b8b2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9400000000-7b0a49d8800ded4cdff4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0zfr-7900000000-52227d0dd814179fde45	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0zmi-9600000000-8ea58ec01176ecce4735	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-9400000000-7bdf5cb6c5aa8c1d607d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-bf04b472392c16bd165c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-483980f183cd4095b2f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-9185cef9251e02ac688c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9200000000-ea836921fe44635e66c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-cf8130e8094c63aa0e25	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052o-9000000000-d175dd460cd717e71350	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-0244ee6a1375f83df3a2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a4c46731c8286baabca9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2900000000-d938708d3f7f8d712710	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ap0-9100000000-a0763e4b908fc98b5853	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9077c11ebfee5a552d35	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Liver
Mammary Gland
Milk
Muscle
Placenta
Prostate Tissue

Pathways

Name	SMPDB/Pathwhiz	KEGG
Propanoate Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29197344	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

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

References

Synthesis Reference

Carlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374.

Material Safety Data Sheet (MSDS)

Not Available

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]

Showing metabocard for 2-Hydroxybutyric acid (BMDB0000008)

Structure for BMDB0000008 (2-Hydroxybutyric acid)