ChemFOnt: Showing chemical card for 3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate (CFc000222046)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:42:30 UTC

Chemfont ID

CFc000222046

Molecule Identification

Common Name

3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate

Definition

3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate is an acylcarnitine. More specifically, it is an methyl 2-(phenylformamido)acetate ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review [Dambrova et al. 2021, Physiological Reviews], acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. Methyl 2-(phenylformamido)acetate is therefore classified as a medium chain AC. As a medium-chain acylcarnitine 3‐{[2‐(phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available at [Dambrova et al. 2021, Physiological Reviews].

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(2-{[1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy}-2-oxoethyl)benzenecarboximidic acid	Generator
Methyl 2-(phenylformamido)acetic acid	Generator, HMDB
3‐{[2‐(phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoic acid	Generator

Chemical Formula

C₁₆H₂₂N₂O₅

Average Molecular Weight

322.361

Monoisotopic Molecular Weight

322.152871816

IUPAC Name

3-{[2-(phenylformamido)acetyl]oxy}-4-(trimethylazaniumyl)butanoate

Traditional Name

3-{[2-(phenylformamido)acetyl]oxy}-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)CC(CC([O-])=O)OC(=O)CNC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H22N2O5/c1-18(2,3)11-13(9-14(19)20)23-15(21)10-17-16(22)12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H-,17,19,20,22)

InChI Key

GWHHQTKAYZEFAI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
N-acyl-alpha amino acid or derivatives
Hippuric acid or derivatives
Alpha-amino acid ester
Alpha-amino acid or derivatives
Benzoic acid or derivatives
Benzamide
Benzoyl
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Carboxylic acid salt
Carboxylic acid ester
Carboxamide group
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

All cells and tissues (PMID: 35710135)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0241793)

Endogenous

Endogenous (HMDB: HMDB0241793)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

Predicted Properties

Property	Value	Source
logP	-3.7	ChemAxon
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	95.53 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	106.11 m³·mol⁻¹	ChemAxon
Polarizability	33.11 Å³	ChemAxon
Number of Rings	1	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

HMDB0241793

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate (CFc000222046)

MOL for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)

3D MOL for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)

3D SDF for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)

3D-SDF for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)

PDB for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)

3D PDB for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)

SMILES for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)

INCHI for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)

Structure for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)

3D Structure for CFc000222046 (3‐{[2‐(Phenylformamido)acetyl]oxy}‐4‐ (trimethylammonio)butanoate)