MiMeDB: Showing metabocard for 3-Hydroxybutyric acid (MMDBc0030364)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:05:23 UTC

Update Date

2024-10-07 04:52:01 UTC

Metabolite ID

MMDBc0030364

Metabolite Identification

Common Name

3-Hydroxybutyric acid

Description

3-Hydroxybutyric acid or beta-hydroxybutyrate belongs to a group of compounds known as ketone bodies. Other ketone bodies include acetoacetate and acetone. 3-hydroxybutyric acid is chiral and so it has 2 enantiomeric forms. (Wikipedia ) In some strains of E. coli, such as E. coli O8 IAI1, the enzyme 3-hydroxybutyrate dehydrogenase (EC:1.1.1.30) catalyzes a reversible redox reaction that converts 3-hydroxybutyric acid to acetoacetate, which can then be converted into acetoacetyl-CoA and participate in fatty acid metabolism. (KEGG). Hydroxybutyrate can also serve as a substrate for short-chain acylCo-A ligase and become a precursor for lipid synthesis.

Structure

MOL SDF PDB SMILES InChI

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

Molecular Formula

C₄H₈O₃

Average Mass

104.1045

Monoisotopic Mass

104.047344122

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

300-85-6

SMILES

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Brain
Feces
Liver
Neuron
Placenta

Tissue Locations

Brain
Liver
Neuron
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0004348	(2S)-Pristanoyl Coenzyme A	3-Hydroxybutyric acid	alpha-methylacyl-CoA racemase	VMH	11060344 11060359
MMDBr0004489	Pristanic acid	3-Hydroxybutyric acid	Not Available	VMH	11356164
MMDBr0004490	Pristanic acid	3-Hydroxybutyric acid	solute carrier family 27 (fatty acid transporter), member 2	VMH	11356164
MMDBr0010197	3-Hydroxybutyric acid	Pristanoyl Coenzyme A	alpha-methylacyl-CoA racemase	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Brain	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000357

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021797

KNApSAcK ID

Not Available

Chemspider ID

428

KEGG Compound ID

C01089

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-hydroxybutyrate

METLIN ID

125

PubChem Compound

441

PDB ID

Not Available

ChEBI ID

20067

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Frenkel G, Peterson RN, Freund M: Oxidative and glycolytic metabolism of semen components by washed guinea pig spermatozoa. Fertil Steril. 1975 Feb;26(2):144-7. doi: 10.1016/s0015-0282(16)40934-9. [PubMed:1126459 ]
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. doi: 10.1016/0378-4347(91)80571-s. [PubMed:2026685 ]
Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. [PubMed:3884391 ]
Geary N, Grotschel H, Scharrer E: Blood metabolites and feeding during postinsulin hypophagia. Am J Physiol. 1982 Sep;243(3):R304-11. doi: 10.1152/ajpregu.1982.243.3.R304. [PubMed:7051864 ]
Kita K, Ishimaru K, Teraoka M, Yanase H, Kato N: Properties of poly(3-hydroxybutyrate) depolymerase from a marine bacterium, Alcaligenes faecalis AE122. Appl Environ Microbiol. 1995 May;61(5):1727-30. doi: 10.1128/aem.61.5.1727-1730.1995. [PubMed:7646009 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. doi: 10.1007/BF00711898. [PubMed:8412012 ]
Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. doi: 10.1007/BF00164476. [PubMed:8579834 ]
Abrahamsson K, Eriksson BO, Holme E, Jodal U, Jonsson A, Lindstedt S: Pivalic acid-induced carnitine deficiency and physical exercise in humans. Metabolism. 1996 Dec;45(12):1501-7. doi: 10.1016/s0026-0495(96)90179-1. [PubMed:8969283 ]
Kamijo T, Indo Y, Souri M, Aoyama T, Hara T, Yamamoto S, Ushikubo S, Rinaldo P, Matsuda I, Komiyama A, Hashimoto T: Medium chain 3-ketoacyl-coenzyme A thiolase deficiency: a new disorder of mitochondrial fatty acid beta-oxidation. Pediatr Res. 1997 Nov;42(5):569-76. doi: 10.1203/00006450-199711000-00002. [PubMed:9357925 ]
Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. doi: 10.1159/000022031. [PubMed:9693263 ]
Pan JW, Rothman TL, Behar KL, Stein DT, Hetherington HP: Human brain beta-hydroxybutyrate and lactate increase in fasting-induced ketosis. J Cereb Blood Flow Metab. 2000 Oct;20(10):1502-7. doi: 10.1097/00004647-200010000-00012. [PubMed:11043913 ]
Krotkiewski M: Value of VLCD supplementation with medium chain triglycerides. Int J Obes Relat Metab Disord. 2001 Sep;25(9):1393-400. doi: 10.1038/sj.ijo.0801682. [PubMed:11571605 ]
Pan JW, Telang FW, Lee JH, de Graaf RA, Rothman DL, Stein DT, Hetherington HP: Measurement of beta-hydroxybutyrate in acute hyperketonemia in human brain. J Neurochem. 2001 Nov;79(3):539-44. doi: 10.1046/j.1471-4159.2001.00575.x. [PubMed:11701757 ]
Blomqvist G, Alvarsson M, Grill V, Von Heijne G, Ingvar M, Thorell JO, Stone-Elander S, Widen L, Ekberg K: Effect of acute hyperketonemia on the cerebral uptake of ketone bodies in nondiabetic subjects and IDDM patients. Am J Physiol Endocrinol Metab. 2002 Jul;283(1):E20-8. doi: 10.1152/ajpendo.00294.2001. [PubMed:12067838 ]
Teresinski G, Buszewicz G, Madro R: The influence of ethanol on the level of ketone bodies in hypothermia. Forensic Sci Int. 2002 Jun 25;127(1-2):88-96. doi: 10.1016/s0379-0738(02)00106-8. [PubMed:12098531 ]
Plecko B, Stoeckler-Ipsiroglu S, Schober E, Harrer G, Mlynarik V, Gruber S, Moser E, Moeslinger D, Silgoner H, Ipsiroglu O: Oral beta-hydroxybutyrate supplementation in two patients with hyperinsulinemic hypoglycemia: monitoring of beta-hydroxybutyrate levels in blood and cerebrospinal fluid, and in the brain by in vivo magnetic resonance spectroscopy. Pediatr Res. 2002 Aug;52(2):301-6. doi: 10.1203/00006450-200208000-00025. [PubMed:12149510 ]
Nalecz KA, Miecz D, Berezowski V, Cecchelli R: Carnitine: transport and physiological functions in the brain. Mol Aspects Med. 2004 Oct-Dec;25(5-6):551-67. doi: 10.1016/j.mam.2004.06.001. [PubMed:15363641 ]
Kim BS, Lee SC, Lee SY, Chang HN, Chang YK, Woo SI: Production of poly(3-hydroxybutyric acid) by fed-batch culture of Alcaligenes eutrophus with glucose concentration control. Biotechnol Bioeng. 1994 Apr 15;43(9):892-8. doi: 10.1002/bit.260430908. [PubMed:18615882 ]
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 ]

Showing metabocard for 3-Hydroxybutyric acid (MMDBc0030364)

MOL for #<Metabolite:0x00007f46f80d7758>

3D MOL for #<Metabolite:0x00007f46f80d7758>

3D SDF for #<Metabolite:0x00007f46f80d7758>

3D-SDF for #<Metabolite:0x00007f46f80d7758>

PDB for #<Metabolite:0x00007f46f80d7758>

3D PDB for #<Metabolite:0x00007f46f80d7758>

SMILES for #<Metabolite:0x00007f46f80d7758>

INCHI for #<Metabolite:0x00007f46f80d7758>

Structure for #<Metabolite:0x00007f46f80d7758>

3D Structure for #<Metabolite:0x00007f46f80d7758>