ChemFOnt: Showing chemical card for N-Acetyltryptophan (CFc000008569)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:24 UTC

Chemfont ID

CFc000008569

Molecule Identification

Common Name

N-Acetyltryptophan

Definition

N-Acetyl-L-tryptophan or N-Acetyltryptophan, 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-Acetyltryptophan can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyltryptophan is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-tryptophan. 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-acetyltryptophan 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 tryptophan can also occur. Many N-acetylamino acids, including N-acetyltryptophan 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 ). N-Acetyltryptophan has also been used as a protein stabilizer. It prevents protein molecules from oxidative degradation by scavenging oxygen dissolved in protein solutions (PMID: 21903216 ). N-Acetyltryptophan has been identified as a catabolite of tryptophan generated by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 28916042 ). N-Acetyltryptophan is an inhibitor of cytochrome c release and an antagonist of the neurokinin 1 receptor (NK-1R). These inhibitory effects are thought have a useful role in neuroprotection. For instance, in mouse models of amyotrophic lateral sclerosis (ALS) the administration of N-Acetyltryptophan has been shown delay disease onset, extend survival, and ameliorate deterioration in motor performance ALS transgenic mice (PMID: 25986728 ). N-acetyltryptophan has been shown to significantly reduce blood-brain barrier permeability and improve functional outcome in rat models of traumatic brain injury (PMID: 29256408 ). N-Acetyltryptophan has also been shown to have a role in preventing hepatic ischemia-reperfusion injury. This is thought to occur through de-activation of the RIP2/caspase/IL-1beta signaling pathway (PMID: 31184936 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-N-Acetyltryptophan	HMDB
Ac-Trp	HMDB
Acetyl-L-Trp	HMDB
Acetyl-L-tryptophan	HMDB
Acetyltryptophan	HMDB
N-Acetyl-L-tryptophan	HMDB
Tryptophan, acetyl	HMDB
N-Acetyltryptophan	MeSH
(2S)-2-Acetamido-3-(1H-indol-3-yl)propanoic acid	HMDB
(2S)-2-Acetamido-3-(1H-indol-3-yl)propionic acid	HMDB
L-N-Acetyltryptophan	HMDB
NAT	HMDB

Chemical Formula

C₁₃H₁₄N₂O₃

Average Molecular Weight

246.2619

Monoisotopic Molecular Weight

246.100442324

IUPAC Name

(2S)-2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

Traditional Name

(2S)-2-[(1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

CAS Registry Number

1218-34-4

SMILES

CC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

InChI Identifier

InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m0/s1

InChI Key

DZTHIGRZJZPRDV-LBPRGKRZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-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

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Indolyl carboxylic acid derivative
3-alkylindole
Indole
Indole or derivatives
Substituted pyrrole
Benzenoid
Acetamide
Heteroaromatic compound
Pyrrole
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:74640 )
L-tryptophan derivative (CHEBI:74640 )

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 18439883)
Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0013713)
Extracellular (HMDB: HMDB0013713)

Source

Endogenous

Endogenous (HMDB: HMDB0013713)

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

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Isovaleric Aciduria (HMDB: HMDB0013713)

Role

Biological role

Metabolite (HMDB: HMDB0013713)
Waste product (PMID: 35448883)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.49 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.81	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	1.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.17 m³·mol⁻¹	ChemAxon
Polarizability	25.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013713

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

700653

PDB ID

Not Available

ChEBI ID

74640

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Acetyltryptophan (CFc000008569)

MOL for CFc000008569 (N-Acetyltryptophan)

3D MOL for CFc000008569 (N-Acetyltryptophan)

3D SDF for CFc000008569 (N-Acetyltryptophan)

3D-SDF for CFc000008569 (N-Acetyltryptophan)

PDB for CFc000008569 (N-Acetyltryptophan)

3D PDB for CFc000008569 (N-Acetyltryptophan)

SMILES for CFc000008569 (N-Acetyltryptophan)

INCHI for CFc000008569 (N-Acetyltryptophan)

Structure for CFc000008569 (N-Acetyltryptophan)

3D Structure for CFc000008569 (N-Acetyltryptophan)