NP-MRD: Showing NP-Card for N-Acetyl-L-methionine (NP0001169)

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Record Information

Version

1.0

Created at

2009-03-03 12:04:46 UTC

Updated at

2021-10-07 20:41:37 UTC

NP-MRD ID

NP0001169

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-L-methionine

Description

N-Acetyl-L-methionine or N-Acetylmethionine, 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-Acetylmethionine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylmethionine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-methionine. 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’s (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-acetylmethionine 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 methionine can also occur. In particular, N-Acetylmethionine can be biosynthesized from L-methionine and acetyl-CoA by the enzyme methionine N-acetyltransferase (EC 2.3.1.66). Excessive amounts N-acetyl amino acids including N-acetylmethionine (as well as N-acetylglycine, N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylthreonine, N-acetylisoleucine, and N-acetylvaline) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618 ). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924 ). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618 ). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylmethionine 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8646.1088645.561   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8646.1088644.023   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8647.4448643.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8648.7778644.023   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8647.4448641.710   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8647.4448646.331   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8648.7778645.561   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8647.4448647.871   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8644.7768646.331   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8643.4438645.561   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0    8642.1098646.331   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0    8640.7678645.561   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S)-2-Acetamido-4-(methylsulfanyl)butanoic acid	ChEBI
Acetyl-L-methionine	ChEBI
Acetylmethionine	ChEBI
AcMet	ChEBI
L-(N-Acetyl)methionine	ChEBI
Methionamine	ChEBI
N-Ac-met	ChEBI
N-Acetylmethionine	ChEBI
Nalpha-acetyl-L-methionine	ChEBI
(2S)-2-Acetamido-4-(methylsulfanyl)butanoate	Generator
(2S)-2-Acetamido-4-(methylsulphanyl)butanoate	Generator
(2S)-2-Acetamido-4-(methylsulphanyl)butanoic acid	Generator
N-Ac-L-methionine	HMDB
N-Acetyl-methionine	HMDB
N-Acetylmethionine monopotassium salt	HMDB
N-Acetylmethionine monosodium salt	HMDB
Hepsan	HMDB
N-Acetylmethionine, (D)-isomer	HMDB
N-Acetylmethionine, (DL)-isomer	HMDB
(2S)-2-Acetamido-4-methylsulfanylbutanoic acid	HMDB
(S)-2-Acetamido-4-(methylthio)butanoic acid	HMDB
Methionin	HMDB
N-Acetyl-L-methionine	KEGG

Chemical Formula

C₇H₁₃NO₃S

Average Mass

191.2480 Da

Monoisotopic Mass

191.06161 Da

IUPAC Name

(2S)-2-acetamido-4-(methylsulfanyl)butanoic acid

Traditional Name

N-acetylmethionine

CAS Registry Number

65-82-7

SMILES

CSCCC(NC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C7H13NO3S/c1-5(9)8-6(7(10)11)3-4-12-2/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)

InChI Key

XUYPXLNMDZIRQH-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine 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

Methionine and derivatives

Alternative Parents

Substituents

Methionine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Thia fatty acid
Fatty acid
Fatty acyl
Acetamide
Secondary carboxylic acid amide
Carboxamide group
Dialkylthioether
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:21557 )
methyl sulfide (CHEBI:21557 )
N-acetyl-L-amino acid (CHEBI:21557 )
L-methionine derivative (CHEBI:21557 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	105.5 °C	Not Available
Boiling Point	453.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	307 at 25 °C	Not Available
LogP	-0.03	Meylan, W. M., & Howard, P. H. (1995). Atom/fragment contribution method for estimating octanol-water partition coefficients. Journal of pharmaceutical sciences, 84(1), 83-92.

Predicted Properties

Property	Value	Source
Water Solubility	6.84 g/L	ALOGPS
logP	-0.15	ALOGPS
logP	-0.11	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	47.03 m³·mol⁻¹	ChemAxon
Polarizability	19.59 Å³	ChemAxon
Number of Rings	0	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

HMDB0011745

DrugBank ID

DB01646

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001089

KNApSAcK ID

Not Available

Chemspider ID

395338

KEGG Compound ID

C02712

BioCyc ID

CPD0-2015

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

448580

PDB ID

Not Available

ChEBI ID

21557

Good Scents ID

rw1265521

References

General References

Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
Ball RO, Courtney-Martin G, Pencharz PB: The in vivo sparing of methionine by cysteine in sulfur amino acid requirements in animal models and adult humans. J Nutr. 2006 Jun;136(6 Suppl):1682S-1693S. [PubMed:16702340 ]
van de Poll MC, Dejong CH, Soeters PB: Adequate range for sulfur-containing amino acids and biomarkers for their excess: lessons from enteral and parenteral nutrition. J Nutr. 2006 Jun;136(6 Suppl):1694S-1700S. [PubMed:16702341 ]
Garlick PJ: Toxicity of methionine in humans. J Nutr. 2006 Jun;136(6 Suppl):1722S-1725S. [PubMed:16702346 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Oehlsen ME, Hegmans A, Qu Y, Farrell N: Effects of geometric isomerism in dinuclear antitumor platinum complexes on their interactions with N-acetyl-L-methionine. J Biol Inorg Chem. 2005 Aug;10(5):433-42. doi: 10.1007/s00775-005-0009-1. Epub 2005 Sep 23. [PubMed:16091934 ]
Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]

Showing NP-Card for N-Acetyl-L-methionine (NP0001169)

MOL for NP0001169 (N-Acetyl-L-methionine)

3D MOL for NP0001169 (N-Acetyl-L-methionine)

3D SDF for NP0001169 (N-Acetyl-L-methionine)

3D-SDF for NP0001169 (N-Acetyl-L-methionine)

PDB for NP0001169 (N-Acetyl-L-methionine)

3D PDB for NP0001169 (N-Acetyl-L-methionine)

SMILES for NP0001169 (N-Acetyl-L-methionine)

INCHI for NP0001169 (N-Acetyl-L-methionine)

Structure for NP0001169 (N-Acetyl-L-methionine)

3D Structure for NP0001169 (N-Acetyl-L-methionine)