ChemFOnt: Showing chemical card for (S)-3-Hydroxybutyric acid (CFc000000337)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:42 UTC

Chemfont ID

CFc000000337

Molecule Identification

Common Name

(S)-3-Hydroxybutyric acid

Definition

(S)-3-Hydroxybutyric acid is a normal human metabolite that has been found elevated in geriatric patients remitting from depression (PMID: 17048218 ). 3-Hydroxybutyric acid is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyric acid are raised in ketosis. In humans, 3-hydroxybutyric acid is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-3-Hydroxybutyric acid	ChEBI
(3S)-3-Hydroxybutyric acid	ChEBI
(S)-3-Hydroxybutanoic acid	ChEBI
(S)-3Hb	ChEBI
(S)-beta-Hydroxybutyric acid	ChEBI
L-(+)-3-Hydroxybutyric acid	ChEBI
L-3-Hydroxybutyric acid	ChEBI
(+)-3-Hydroxybutyrate	Generator
(3S)-3-Hydroxybutyrate	Generator
(S)-3-Hydroxybutanoate	Generator
(S)-b-Hydroxybutyrate	Generator
(S)-b-Hydroxybutyric acid	Generator
(S)-beta-Hydroxybutyrate	Generator
(S)-Β-hydroxybutyrate	Generator
(S)-Β-hydroxybutyric acid	Generator
L-(+)-3-Hydroxybutyrate	Generator
L-3-Hydroxybutyrate	Generator
(S)-3-Hydroxybutyrate	Generator
(+)-3-Hydroxy-N-butyric acid	HMDB
(3S)-3-Hydroxy-butanoate	HMDB
(3S)-3-Hydroxy-butanoic acid	HMDB
(S)-3-Hydroxy-2-methyl-propanoate	HMDB
(S)-3-Hydroxy-2-methyl-propanoic acid	HMDB
(S)-3-Hydroxy-butanoate	HMDB
(S)-3-Hydroxy-butanoic acid	HMDB
(S)-b-Hydroxyisobutyrate	HMDB
(S)-b-Hydroxyisobutyric acid	HMDB
(S)-beta-Hydroxyisobutyrate	HMDB
(S)-beta-Hydroxyisobutyric acid	HMDB
L-(+)-2-Methyl-hydracrylate	HMDB
L-(+)-2-Methyl-hydracrylic acid	HMDB
L-(+)-b-Hydroxyisobutyrate	HMDB
L-(+)-b-Hydroxyisobutyric acid	HMDB
L-(+)-beta-Hydroxyisobutyrate	HMDB
L-(+)-beta-Hydroxyisobutyric acid	HMDB
L-beta-Hydroxybutyrate	HMDB
(3S)-3-Hydroxybutanoic acid	HMDB
(S)-(+)-beta-Hydroxybutyric acid	HMDB
(S)-(+)-Β-hydroxybutyric acid	HMDB
(S)-beta-Hydroxybutanoic acid	HMDB
(S)-Β-hydroxybutanoic acid	HMDB
3-Hydroxy-N-butyric acid	HMDB
3-Hydroxybutanoic acid	HMDB
3-Hydroxybutyric acid	HMDB
L-beta-Hydroxybutyric acid	HMDB
L-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
(S)-3-Hydroxybutyric acid	HMDB

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

IUPAC Name

(3S)-3-hydroxybutanoic acid

Traditional Name

β-hydroxybutyrate,l

CAS Registry Number

6168-83-8

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-/m0/s1

InChI Key

WHBMMWSBFZVSSR-VKHMYHEASA-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-hydroxybutyric acid (CHEBI:17290 )

Functional Ontology

Not Available

Adipose tissue (HMDB: HMDB0000442)
Adipose tissue (HMDB: HMDB0000442)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000442)
Skeletal muscle (HMDB: HMDB0000442)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2614280)

Tissue substructure

Muscle (HMDB: HMDB0000442)

Cell

Nerve cell (HMDB: HMDB0000442)
Neuron (HMDB: HMDB0000442)

Organ

Brain (HMDB: HMDB0000442)

Excreta

Biofluid or Excreta

Urine (PMID: 14708889)

Cellular substructure

Cytoplasm (HMDB: HMDB0000442)

Organelle

Mitochondrion (HMDB: HMDB0000442)

Source

Endogenous

Endogenous (HMDB: HMDB0000442)

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

Not Available

Role

Not Available

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	9.94 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