ChemFOnt: Showing chemical card for 3-Hydroxybutyric acid (CFc000000004)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:34:04 UTC

Chemfont ID

CFc000000004

Molecule Identification

Common Name

3-Hydroxybutyric acid

Definition

3-Hydroxybutyric acid (CAS: 300-85-6), also known as beta-hydroxybutanoic acid, is a typical partial-degradation product of branched-chain amino acids (primarily valine) released from muscle for hepatic and renal gluconeogenesis. This acid is metabolized by 3-hydroxybutyrate dehydrogenase (catalyzes the oxidation of 3-hydroxybutyrate to form acetoacetate, using NAD+ as an electron acceptor). The enzyme functions in nervous tissues and muscles, enabling the use of circulating hydroxybutyrate as a fuel. In the liver mitochondrial matrix, the enzyme can also catalyze the reverse reaction, a step in ketogenesis. 3-Hydroxybutyric acid is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid, and 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 humans, 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 the 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 the synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first two 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 dipalmitoylphosphatidylcholine, 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 ). 3-Hydroxybutyric acid is found to be associated with fumarase deficiency and medium-chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism. 3-Hydroxybutyric acid is a metabolite of Alcaligenes and can be produced from plastic metabolization or incorporated into polymers, depending on the species (PMID: 7646009 , 18615882 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-(-)-beta-Hydroxybutyric acid	ChEBI
(R)-3-Hydroxybutanoic acid	ChEBI
3-D-Hydroxybutyric acid	ChEBI
D-3-Hydroxybutyric acid	ChEBI
D-beta-Hydroxybutyric acid	Kegg
(R)-(-)-b-Hydroxybutyrate	Generator
(R)-(-)-b-Hydroxybutyric acid	Generator
(R)-(-)-beta-Hydroxybutyrate	Generator
(R)-(-)-Β-hydroxybutyrate	Generator
(R)-(-)-Β-hydroxybutyric acid	Generator
(R)-3-Hydroxybutanoate	Generator
3-D-Hydroxybutyrate	Generator
D-3-Hydroxybutyrate	Generator
D-b-Hydroxybutyrate	Generator
D-b-Hydroxybutyric acid	Generator
D-beta-Hydroxybutyrate	Generator
D-Β-hydroxybutyrate	Generator
D-Β-hydroxybutyric acid	Generator
(R)-3-Hydroxybutyrate	Generator
3-delta-Hydroxybutyrate	HMDB
3-delta-Hydroxybutyric acid	HMDB
BHIB	HMDB
D-(-)-3-Hydroxybutyrate	HMDB
delta-(-)-3-Hydroxybutyrate	HMDB
delta-3-Hydroxybutyrate	HMDB
delta-3-Hydroxybutyric acid	HMDB
delta-beta-Hydroxybutyrate	HMDB
3R-Hydroxy-butanoate	HMDB
(R)-3-Hydroxybutyric acid	KEGG
(-)-3-Hydroxy-n-butyric acid	HMDB
(-)-3-Hydroxybutyric acid	HMDB
(3R)-3-Hydroxybutanoic acid	HMDB
(3R)-3-Hydroxybutyric acid	HMDB
(3R)-Hydroxybutyrate	HMDB
(R)-(-)-3-Hydroxybutyric acid	HMDB
(R)-beta-Hydroxybutanoic acid	HMDB
(R)-beta-Hydroxybutyric acid	HMDB
(R)-β-Hydroxybutanoic acid	HMDB
(R)-β-Hydroxybutyric acid	HMDB
3-Hydroxy-n-butyric acid	HMDB
3-Hydroxybutanoic acid	HMDB
3-Hydroxybutyric acid	HMDB
3R-Hydroxybutanoic acid	HMDB
D-(-)-3-Hydroxybutanoic acid	HMDB
D-(-)-3-Hydroxybutyric acid	HMDB
D-(-)-beta-Hydroxybutyric acid	HMDB
D-(-)-β-Hydroxybutyric acid	HMDB
beta-Hydroxy-n-butyric acid	HMDB
beta-Hydroxybutanoic acid	HMDB
beta-Hydroxybutyric acid	HMDB
β-Hydroxy-n-butyric acid	HMDB
β-Hydroxybutanoic acid	HMDB
β-Hydroxybutyric acid	HMDB

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

IUPAC Name

(3R)-3-hydroxybutanoic acid

Traditional Name

(-)-3-hydroxybutyric acid

CAS Registry Number

625-72-9

SMILES

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

InChI Identifier

InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1

InChI Key

WHBMMWSBFZVSSR-GSVOUGTGSA-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

ketone body (CHEBI:17066 )
3-hydroxybutyric acid (CHEBI:17066 )
Hydroxy fatty acids (LMFA01050243 )

Functional Ontology

Physiological effect

Health effect

Endocrine system disorder

Diabetes mellitus type 2 (HMDB: HMDB0000011)

Nervous system disorder

Central nervous system disorder

Meningitis (HMDB: HMDB0000011)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18184896)
Cerebrospinal Fluid (CSF) (PMID: 9693263)
Cellular Cytoplasm (PMID: 8579834)
Saliva (PMID: 22308371)
Cerebrospinal fluid (HMDB: HMDB0000011)

Excreta

Biofluid or Excreta

Urine (PMID: 6321058)
Feces (PMID: 20669995)

Cellular substructure

Cytoplasm (HMDB: HMDB0000011)
Extracellular (HMDB: HMDB0000011)

Organelle

Mitochondrion (HMDB: HMDB0000011)

Cell

Neuron (HMDB: HMDB0000011)

Organ

Brain (HMDB: HMDB0000011)
Liver (HMDB: HMDB0000011)

Source

Endogenous

Endogenous (HMDB: HMDB0000011)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Role

Biological role

Human metabolite (HMDB: HMDB0000011)

Industrial application

Pharmaceutical industry

Biomarker

Preeclampsia/Eclampsia (MarkerDB: MDB00000005)
Pregnancy (MarkerDB: MDB00000005)
Obesity (MarkerDB: MDB00000005)
Diabetes mellitus type 2 (MarkerDB: MDB00000005)
Schizophrenia (MarkerDB: MDB00000005)
3 Hydroxy 3 Methylglutaryl Co A Lyase Deficiency (MarkerDB: MDB00000005)
Medium Chain Acyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00000005)
Meningitis (MarkerDB: MDB00000005)
Pyruvate Dehydrogenase Phosphatase Deficiency (MarkerDB: MDB00000005)
Fumarase deficiency (MarkerDB: MDB00000005)
Pyruvate carboxylase deficiency (MarkerDB: MDB00000005)
3 Hydroxyacyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00000005)
Anoxia (MarkerDB: MDB00000005)
Carnitine palmitoyltransferase I deficiency (MarkerDB: MDB00000005)
Long Chain 3 Hydroxyacyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00000005)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	539 g/L	ALOGPS
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	9.96 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

External Links

HMDB ID

HMDB0000011

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021869

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Beta-Hydroxybutyric_acid

METLIN ID

Not Available

PubChem Compound

92135

PDB ID

Not Available

ChEBI ID

17066

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Le Sann, Christine; Munoz, Dulce M.; Saunders, Natalie; Simpson, Thomas J.; Smith, David I.; Soulas, Florilene; Watts, Paul; Willis, Christine L. Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of b-hydroxycarbonyl compounds. Org Biomol Chem. 2005 May 7;3(9):1719-28. Epub 2005 Mar 31. Pubmed: 15858656

Showing chemical card for 3-Hydroxybutyric acid (CFc000000004)

MOL for CFc000000004 (3-Hydroxybutyric acid)

3D MOL for CFc000000004 (3-Hydroxybutyric acid)

3D SDF for CFc000000004 (3-Hydroxybutyric acid)

3D-SDF for CFc000000004 (3-Hydroxybutyric acid)

PDB for CFc000000004 (3-Hydroxybutyric acid)

3D PDB for CFc000000004 (3-Hydroxybutyric acid)

SMILES for CFc000000004 (3-Hydroxybutyric acid)

INCHI for CFc000000004 (3-Hydroxybutyric acid)

Structure for CFc000000004 (3-Hydroxybutyric acid)

3D Structure for CFc000000004 (3-Hydroxybutyric acid)