Livestock Metabolome Database: Showing metabocard for 3-Hydroxybutyric acid (LMDB00144)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:19 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00144

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Hydroxybutyric acid

Description

3-Hydroxybutyric acid (or beta-hydroxybutyrate) is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyrate in blood and urine are raised in ketosis. In animals, 3-hydroxybutyrate is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low. Blood levels of 3-Hydroxybutyric acid levels may be monitored in diabetic patients to look for diabetic ketoacidosis. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing mammals. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies is utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life. (PMID 3884391 ).

Structure

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

Synonyms

Value	Source
(1)-3-Hydroxybutyric acid	ChEBI
3 HBA	ChEBI
3-Hydroxybuttersaeure	ChEBI
3-OH-Butyric acid	ChEBI
beta-Hydroxy-N-butyric acid	ChEBI
beta-Hydroxybutanoic acid	ChEBI
beta-Hydroxybuttersaeure	ChEBI
beta-Hydroxybutyric acid	ChEBI
BHBA	ChEBI
DL-beta-Hydroxybutyric acid	ChEBI
(1)-3-Hydroxybutyrate	Generator
3-OH-Butyrate	Generator
b-Hydroxy-N-butyrate	Generator
b-Hydroxy-N-butyric acid	Generator
beta-Hydroxy-N-butyrate	Generator
Β-hydroxy-N-butyrate	Generator
Β-hydroxy-N-butyric acid	Generator
b-Hydroxybutanoate	Generator
b-Hydroxybutanoic acid	Generator
beta-Hydroxybutanoate	Generator
Β-hydroxybutanoate	Generator
Β-hydroxybutanoic acid	Generator
b-Hydroxybuttersaeure	Generator
Β-hydroxybuttersaeure	Generator
b-Hydroxybutyrate	Generator
b-Hydroxybutyric acid	Generator
beta-Hydroxybutyrate	Generator
Β-hydroxybutyrate	Generator
Β-hydroxybutyric acid	Generator
DL-b-Hydroxybutyrate	Generator
DL-b-Hydroxybutyric acid	Generator
DL-beta-Hydroxybutyrate	Generator
DL-Β-hydroxybutyrate	Generator
DL-Β-hydroxybutyric acid	Generator
3-Hydroxybutyrate	Generator
3-Hydroxy-butanoate	HMDB
3-Hydroxy-butanoic acid	HMDB
3-Hydroxy-butyrate	HMDB
3-Hydroxy-butyric acid	HMDB
3-Hydroxybutanoate	HMDB
3-Hydroxybutanoic acid	HMDB
Biopol	HMDB
DL-3-Hydroxybutyrate	HMDB
DL-3-Hydroxybutyric acid	HMDB
beta Hydroxybutyric acid	HMDB
3 Hydroxybutyric acid	HMDB
beta Hydroxybutyrate	HMDB
(+ -)-3-Hydroxybutyric acid	HMDB
3 Hydroxybutyrate	HMDB

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

IUPAC Name

3-hydroxybutanoic acid

Traditional Name

3 hydroxybutyrate

CAS Registry Number

300-85-6

SMILES

CC(O)CC(O)=O

InChI Identifier

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

InChI Key

WHBMMWSBFZVSSR-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Short-chain hydroxy acid
Beta-hydroxy acid
Fatty 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

3-hydroxy monocarboxylic acid (CHEBI:20067 )
hydroxybutyric acid (CHEBI:20067 )
(omega-1)-hydroxy fatty acid (CHEBI:20067 )
Hydroxy fatty acids (LMFA01050005 )

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	-0.5	ALOGPS
logP	-0.39	ChemAxon
logS	0.71	ALOGPS
pKa (Strongest Acidic)	4.41	ChemAxon
pKa (Strongest Basic)	-2.6	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	23.46 m³·mol⁻¹	ChemAxon
Polarizability	10.01 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)	splash10-0002-0900000000-92be5c49a099fe1d9865	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-01ot-1920000000-c93138bf9d35643fef30	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00dj-8900000000-e632e14fb4be28bdb786	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014l-1900000000-e192caba63f034040624	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-92be5c49a099fe1d9865	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01ot-1920000000-c93138bf9d35643fef30	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-8900000000-e632e14fb4be28bdb786	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014l-1900000000-e192caba63f034040624	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-d06c5ac1a3733a38ea05	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9000000000-63f261a4dc876e264246	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01ei-9710000000-2652bd46b41e50defdb0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-9200000000-4156904e7472b5e97249	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9300000000-505ae46abb0c49c78b1e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfr-9600000000-dfed69c37c1a4d794440	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0zfr-4900000000-537084557f5986f16b31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-4900000000-537084557f5986f16b31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-9000000000-7f0ec480b3c3c3911acd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-9100000000-05c4623b015ff4300a6d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n0-9000000000-cbe0653845ffe4dc6ad4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e55d47308c7464e4cb22	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-8900000000-06dfbf939f6d19983ebe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9200000000-48b6e9b8656d41bff9cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-f7d61596ff4428fe6b09	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0007-9000000000-7fc414806153ebd8822c	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
2D NMR	[1H,1H] 2D 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

Colostrum
Kidney perfusate
Meat
Milk
Plasma
Ruminal Fluid
Serum
Synovial Fluid
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Kidney perfusate	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502759	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.86+/-0.18 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.94+/-0.26 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	1.26+/-0.42 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	1.47+/-0.39 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23738862	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23497994	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23182357	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	12-121 uM	Not Available	Bovine	22098372	details
Milk	Detected and Quantified	10-531 uM	Not Available	Bovine	20338431	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	22370585	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	24937646	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24440255	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	21496096	details
Plasma	Detected and Quantified	2970 +/- 784 uM	Not Available	Bovine	Abdullah BAŞOĞLU,...	details
Plasma	Detected and Quantified	4547 +/- 1058 uM	Not Available	Bovine	Abdullah BAŞOĞLU,...	details
Plasma	Detected and Quantified	8042 +/- 1256 uM	Not Available	Bovine	Abdullah BAŞOĞLU,...	details
Plasma	Detected and Quantified	1550 +/- 170 uM	Not Available	Bovine	Abdullah BAŞOĞLU,...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	Trabi M, Keller M...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Plasma	Detected and Quantified	500 +/- 30 uM	Not Available	Bovine	Abdullah BAŞOĞLU,...	details
Plasma	Detected and Quantified	640 +/- 90 uM	Not Available	Bovine	Abdullah BAŞOĞLU,...	details
Ruminal Fluid	Detected and Quantified	131 +/- 8.0 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	76.5 +/- 17 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	80.1 +/- 9.4 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	110 +/- 40 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	53 +/- 12 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	63 +/- 13 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	63 +/- 13 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	77 +/- 13 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	90 +/- 23 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	606.3 +/- 14 uM	Not Available	Caprine	22706048	details
Ruminal Fluid	Detected and Quantified	63.3 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	78.6 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	89.4 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	109.9 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	44.8 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	46.7 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	60.6 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	77.1 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	553.7811 +/- 209.1351 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	631.5763 +/- 313.5592 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	596.9241 +/- 169.5479 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	161.92 +/- 54.25 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	353.1989 +/- 176.1426 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	543.6782 +/- 157.9971 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	400.0996 +/- 123.3543 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	375.1492 +/- 203.0711 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	411.6994 +/- 128.4455 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	532.6358 +/- 197.8191 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	389.7844 +/- 116.8778 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	573.6844 +/- 247.6773 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	402.9691 +/- 108.4581 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	676.5352 +/- 396.5541 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	412.8304 +/- 110.7007 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	339.8844 +/- 167.5501 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	568.025 +/- 226.7049 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	417.7539 +/- 123.8176 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	672.3698 +/- 331.2823 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	391.6459 +/- 137.4591 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	376.2224 +/- 171.489 uM	Normal	Ovine	Goldansaz et al.,...	details
Synovial Fluid	Detected but not Quantified	Not Applicable	Not Available	Ovine	25283885	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details