ChemFOnt: Showing chemical card for 3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid (CFc000230315)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:57:46 UTC

Chemfont ID

CFc000230315

Molecule Identification

Common Name

3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid

Definition

Pantothenic acid, also known as pantothenate, belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. Net microbial synthesis of pantothenic acid in the rumen of steer calves has been estimated to be 2.2 mg/kg of digestible organic matter consumed per day. Pantothenic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, pantothenic acid is involved in the metabolic disorder called the gaba-transaminase deficiency pathway. Outside of the human body, Pantothenic acid is found, on average, in the highest concentration within a few different foods, such as jew's ears, shiitakes, and snack bars and in a lower concentration in common buckwheats, enokitakes, and cheeses. Pantothenic acid has also been detected, but not quantified in, several different foods, such as tallows, other cereal products, gadiformes, cinnamons, and charrs. This could make pantothenic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(2,4-Dihydroxy-3,3-dimethylbutanoyl)-beta-alanine	ChEBI
N-(2,4-Dihydroxy-3,3-dimethylbutanoyl)-b-alanine	Generator
N-(2,4-Dihydroxy-3,3-dimethylbutanoyl)-β-alanine	Generator
Pantothenate	Generator
(+)-Pantothenate	HMDB
(+)-Pantothenic acid	HMDB
(D)-(+)-Pantothenate	HMDB
(D)-(+)-Pantothenic acid	HMDB
(R)-Pantothenate	HMDB
Chick antidermatitis factor	HMDB
D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-b-alanine	HMDB
D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-beta-alanine	HMDB
D-Pantothenate	HMDB
D-Pantothenic acid	HMDB
delta-Pantothenate	HMDB
delta-Pantothenic acid	HMDB
Vitamin b5	HMDB
DL-Pantothenate	Generator

Chemical Formula

C₉H₁₇NO₅

Average Molecular Weight

219.235

Monoisotopic Molecular Weight

219.110672659

IUPAC Name

3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoic acid

Traditional Name

pantothenic acid

CAS Registry Number

599-54-2

SMILES

CC(C)(CO)C(O)C(O)=NCCC(O)=O

InChI Identifier

InChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)

InChI Key

GHOKWGTUZJEAQD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Fatty amide
Monosaccharide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

pantothenic acids (CHEBI:7916 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.23 g/L	ALOGPS
logP	-0.83	ALOGPS
logP	-1.4	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	51.51 m³·mol⁻¹	ChemAxon
Polarizability	21.92 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

Not Available

DrugBank ID

DB01783

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008322

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pantothenic_acid

METLIN ID

Not Available

PubChem Compound

988

PDB ID

Not Available

ChEBI ID

7916

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid (CFc000230315)

MOL for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)

3D MOL for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)

3D SDF for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)

3D-SDF for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)

PDB for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)

3D PDB for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)

SMILES for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)

INCHI for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)

Structure for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)

3D Structure for CFc000230315 (3-[[(2S)-2,4-Dihydroxy-3,3-dimethylbutanoyl]amino]propanoic acid)