MiMeDB: Showing metabocard for N-Acetylvaline (MMDBc0000460)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:38:16 UTC

Update Date

2022-08-31 06:06:58 UTC

MiMeDB ID

MMDBc0000460

Metabolite Identification

Common Name

N-Acetylvaline

Description

N-Acetyl-L-valine or N-Acetylvaline, 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-Acetylvaline can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylvaline is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-valine. 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-acetylvaline 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 valine can also occur. Excessive amounts N-acetyl amino acids including N-acetylvaline(as well as N-acetylglycine, N-acetylserine, N-acetylmethionine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylglutamine, N-acetylisoleucine, and N-acetylthreonine) 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-acetylthreonine, 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

Synonyms

Value	Source
(2S)-2-Acetamido-3-methylbutanoic acid	ChEBI
(2S)-2-Acetamido-3-methylbutanoate	Generator
N-Acetylvaline, (L)-isomer	HMDB
N-Acetyl-DL-valine	HMDB
N-Acetylvaline, (D)-isomer	HMDB
Acetyl-val	HMDB
N-Acetyl-D,L-valine	HMDB
(S)-2-Acetamido-3-methylbutanoic acid	HMDB
2-Acetamido-3-methylbutanoic acid	HMDB
Acetylvaline	HMDB
L-N-Acetylvaline	HMDB
N-Acetyl-L-valine	HMDB
N-Acetylvaline	ChEBI

Chemical Formula

C₇H₁₃NO₃

Average Molecular Weight

159.185

Monoisotopic Molecular Weight

159.089543283

IUPAC Name

(2S)-2-acetamido-3-methylbutanoic acid

Traditional Name

L-valine, N-acetyl-

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](NC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m0/s1

InChI Key

IHYJTAOFMMMOPX-LURJTMIESA-N

Chemical Taxonomy

Description

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

Valine and derivatives

Alternative Parents

Substituents

N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Valine or derivatives
N-acyl-l-alpha-amino acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	25.6 g/L	ALOGPS
logP	0.29	ALOGPS
logP	0.13	ChemAxon
logS	-0.79	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-1.6	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	3	ChemAxon
Refractivity	38.94 m³·mol⁻¹	ChemAxon
Polarizability	16.27 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0910000000-eb15d3e402321f301a5b	2019-11-14	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-1900000000-f13ad129a67fb49cd5f1	2019-11-14	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0910000000-eb15d3e402321f301a5b	2019-11-14	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03di-1900000000-f13ad129a67fb49cd5f1	2019-11-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-2900000000-62b894411c752f8b084d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-074j-9400000000-ca68eb9560bb85f3f0a3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-93cbf0596455b06e2177	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-8a3ea4752da910c1d6aa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2900000000-20d16dff6f6a857ac3b2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-a172b952357a69192051	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.54 MHz, DMSO-d6, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Firmicutes	5		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620	details
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050	details
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030	details

External Links

HMDB ID

HMDB0011757

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028427

KNApSAcK ID

Not Available

Chemspider ID

60154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66789

PDB ID

Not Available

ChEBI ID

21565

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

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. doi: 10.1086/500563. Epub 2006 Jan 18. [PubMed:16465618 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for N-Acetylvaline (MMDBc0000460)

MOL for #<Metabolite:0x000055b76dc063e8>

3D MOL for #<Metabolite:0x000055b76dc063e8>

3D SDF for #<Metabolite:0x000055b76dc063e8>

3D-SDF for #<Metabolite:0x000055b76dc063e8>

PDB for #<Metabolite:0x000055b76dc063e8>

3D PDB for #<Metabolite:0x000055b76dc063e8>

SMILES for #<Metabolite:0x000055b76dc063e8>

INCHI for #<Metabolite:0x000055b76dc063e8>

Structure for #<Metabolite:0x000055b76dc063e8>

3D Structure for #<Metabolite:0x000055b76dc063e8>