ChemFOnt: Showing chemical card for N-Acetylproline (CFc000075110)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 20:37:21 UTC

Chemfont ID

CFc000075110

Molecule Identification

Common Name

N-Acetylproline

Definition

N-Acetyl-L-proline or N-Acetylproline, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylproline can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylproline is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-proline. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT‚Äôs (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylproline can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free proline can also occur. Many N-acetylamino acids, including N-acetylproline are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-1-Acetylpyrrolidine-2-carboxylic acid	ChEBI
Acetylproline	ChEBI
(2S)-1-Acetylpyrrolidine-2-carboxylate	Generator

Chemical Formula

C₇H₁₁NO₃

Average Molecular Weight

157.1671

Monoisotopic Molecular Weight

157.073893223

IUPAC Name

(2S)-1-acetylpyrrolidine-2-carboxylic acid

Traditional Name

acetylproline

CAS Registry Number

68-95-1

SMILES

[H][C@]1(CCCN1C(C)=O)C(O)=O

InChI Identifier

InChI=1S/C7H11NO3/c1-5(9)8-4-2-3-6(8)7(10)11/h6H,2-4H2,1H3,(H,10,11)/t6-/m0/s1

InChI Key

GNMSLDIYJOSUSW-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Proline or derivatives
N-acyl-l-alpha-amino acid
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Tertiary carboxylic acid amide
Acetamide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organoheterocyclic compound
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-proline derivative (CHEBI:21560 )
pyrrolidinemonocarboxylic acid (CHEBI:21560 )
N-acylpyrrolidine (CHEBI:21560 )
N-acetyl-L-amino acid (CHEBI:21560 )

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Feces (PMID: 27275383)

Source

Exogenous

Exogenous (HMDB: HMDB0094701)

Process

Not Available

Role

Biological role

Waste product (PMID: 35448883)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	517 g/L	ALOGPS
logP	-0.51	ALOGPS
logP	-0.49	ChemAxon
logS	0.52	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.63 m³·mol⁻¹	ChemAxon
Polarizability	15.47 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

HMDB0094701

DrugBank ID

DB03360

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

66141

PDB ID

N7P

ChEBI ID

21560

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Acetylproline (CFc000075110)

MOL for CFc000075110 (N-Acetylproline)

3D MOL for CFc000075110 (N-Acetylproline)

3D SDF for CFc000075110 (N-Acetylproline)

3D-SDF for CFc000075110 (N-Acetylproline)

PDB for CFc000075110 (N-Acetylproline)

3D PDB for CFc000075110 (N-Acetylproline)

SMILES for CFc000075110 (N-Acetylproline)

INCHI for CFc000075110 (N-Acetylproline)

Structure for CFc000075110 (N-Acetylproline)

3D Structure for CFc000075110 (N-Acetylproline)