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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:59 UTC

HMDB ID

HMDB0000766

Secondary Accession Numbers

HMDB00766

Metabolite Identification

Common Name

N-Acetyl-L-alanine

Description

N-Acetyl-L-alanine or N-Acetylalanine, 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-Acetyl-L-alanine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-alpha-Acetyl-L-alanine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-alanine. 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-Acetyl-L-alanine is a product of the enzyme known as ribosomal alanine N-acetyltransferase (EC 2.3.1.128) which catalyzes the transfer of the acetyl group of acetyl CoA to proteins bearing an N-terminal alanine. N-acetylated amino acids, such as N-acetylalanine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). Excessive amounts N-acetyl amino acids can be detected in the urine with individuals with aminoacylase I deficiency, a genetic disorder (PMID: 16465618 ). These include N-acetylalanine (as well as N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylglycine, N-acetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, N-acetylvaline and N-acetylisoleucine. 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-acetylalanine, are classified as uremic toxins (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-Acetyl-L-alanine has been identified in the human placenta (PMID: 32033212 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-2-(Acetylamino)propanoic acid	ChEBI
2-Acetamidopropionic acid	ChEBI
Ac-ala-OH	ChEBI
Acetylalanine	ChEBI
L-N-Acetylalanine	ChEBI
N-Acetyl-L-alpha-alanine	ChEBI
N-Acetyl-S-alanine	ChEBI
N-Acetylalanine	ChEBI
(S)-2-(Acetylamino)propanoate	Generator
2-Acetamidopropionate	Generator
N-Acetyl-L-a-alanine	Generator
N-Acetyl-L-α-alanine	Generator
(S)-(-)-N-Acetylalanine	HMDB
(S)-N-Acetylalanine	HMDB
Acetyl-L-alanine	HMDB
N-Acetyl-(S)-alanine	HMDB

Chemical Formula

C₅H₉NO₃

Average Molecular Weight

131.1299

Monoisotopic Molecular Weight

131.058243159

IUPAC Name

(2S)-2-acetamidopropanoic acid

Traditional Name

N-acetylalanine

CAS Registry Number

97-69-8

SMILES

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

InChI Identifier

InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m0/s1

InChI Key

KTHDTJVBEPMMGL-VKHMYHEASA-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
Alanine or derivatives
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-alanine derivative (CHEBI:40992 )
N-acetyl-L-amino acid (CHEBI:40992 )

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

Organ

Placenta (HMDB: HMDB0000766)

Excreta

Biofluid or Excreta

Urine (PMID: 19212411)
Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0000766)

Source

Exogenous

Exogenous (HMDB: HMDB0000766)

Food

Animal origin

Poultry

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)

Endogenous

Endogenous (HMDB: HMDB0000766)

Process

Naturally occurring process

Biological process

Biochemical pathway

Prostate cancer (HMDB: HMDB0000766)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000766)

Biological role

Waste product (PMID: 35448883)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	43.6 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	-0.76	ChemAxon
logS	-0.48	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-2	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	2	ChemAxon
Refractivity	29.94 m³·mol⁻¹	ChemAxon
Polarizability	12.5 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.367	31661259
DarkChem	[M-H]-	126.608	31661259
AllCCS	[M+H]+	131.956	32859911
AllCCS	[M-H]-	126.622	32859911
DeepCCS	[M+H]+	124.474	30932474
DeepCCS	[M-H]-	120.774	30932474
DeepCCS	[M-2H]-	158.016	30932474
DeepCCS	[M+Na]+	133.195	30932474
AllCCS	[M+H]+	132.0	32859911
AllCCS	[M+H-H2O]+	127.9	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	136.8	32859911
AllCCS	[M-H]-	126.6	32859911
AllCCS	[M+Na-2H]-	129.4	32859911
AllCCS	[M+HCOO]-	132.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-alanine	C[C@H](NC(C)=O)C(O)=O	2051.9	Standard polar	33892256
N-Acetyl-L-alanine	C[C@H](NC(C)=O)C(O)=O	1166.3	Standard non polar	33892256
N-Acetyl-L-alanine	C[C@H](NC(C)=O)C(O)=O	1325.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-alanine,1TMS,isomer #1	CC(=O)N[C@@H](C)C(=O)O[Si](C)(C)C	1245.3	Semi standard non polar	33892256
N-Acetyl-L-alanine,1TMS,isomer #2	CC(=O)N([C@@H](C)C(=O)O)[Si](C)(C)C	1289.7	Semi standard non polar	33892256
N-Acetyl-L-alanine,2TMS,isomer #1	CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1307.4	Semi standard non polar	33892256
N-Acetyl-L-alanine,2TMS,isomer #1	CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1298.8	Standard non polar	33892256
N-Acetyl-L-alanine,2TMS,isomer #1	CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1447.1	Standard polar	33892256
N-Acetyl-L-alanine,1TBDMS,isomer #1	CC(=O)N[C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C	1478.1	Semi standard non polar	33892256
N-Acetyl-L-alanine,1TBDMS,isomer #2	CC(=O)N([C@@H](C)C(=O)O)[Si](C)(C)C(C)(C)C	1536.9	Semi standard non polar	33892256
N-Acetyl-L-alanine,2TBDMS,isomer #1	CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1768.2	Semi standard non polar	33892256
N-Acetyl-L-alanine,2TBDMS,isomer #1	CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1760.6	Standard non polar	33892256
N-Acetyl-L-alanine,2TBDMS,isomer #1	CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1750.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-alanine GC-MS (1 TMS)	splash10-05n0-2900000000-c0a5e66723f41ac78751	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-alanine GC-MS (Non-derivatized)	splash10-05n0-2900000000-c0a5e66723f41ac78751	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-alanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-82510327b6f9313f2dec	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-alanine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9200000000-5c8085960ac907268dee	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-alanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-alanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-alanine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-alanine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-alanine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0006-9000000000-4cea4517104b7a324deb	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9000000000-4497242e6b422cf3f913	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9000000000-22d764f7b773b82c6515	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine LC-ESI-IT , negative-QTOF	splash10-000i-9000000000-e6becb5f8b8bbb53304a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 10V, Negative-QTOF	splash10-000i-9000000000-0aae7c100ca236c5d9ff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 35V, Negative-QTOF	splash10-000i-9000000000-a834937166d1b13573af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 20V, Negative-QTOF	splash10-000i-9000000000-64d13cbfedb6b9468f0f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 40V, Negative-QTOF	splash10-0079-9500000000-47ed2f6ecfc2c07a7238	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 10V, Positive-QTOF	splash10-0006-9000000000-381b773ca35cc4fcd019	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 20V, Positive-QTOF	splash10-0006-9000000000-5f8b9c01b2c31f02a57c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 40V, Positive-QTOF	splash10-0006-9000000000-bb702a57406742ce92fd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 35V, Positive-QTOF	splash10-0006-9000000000-bcbc1b15a23596134e9b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 20V, Positive-QTOF	splash10-0006-9000000000-dcbe526c53d0cc355023	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 10V, Positive-QTOF	splash10-0006-9000000000-9c03cb4f6a9e3f4d7d8d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 40V, Positive-QTOF	splash10-0006-9000000000-7ab7ce4fbeeaa4906786	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-alanine 35V, Negative-QTOF	splash10-000i-9000000000-f747c686b81495308cfc	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-alanine 10V, Positive-QTOF	splash10-0019-9600000000-98787fdcdf179af3efc6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-alanine 20V, Positive-QTOF	splash10-000f-9000000000-c9b855453cf3c68830bf	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-alanine 40V, Positive-QTOF	splash10-0006-9000000000-4178e09fa261bbb5e7e9	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-alanine 10V, Negative-QTOF	splash10-001i-4900000000-2739a6e8536aca9442cc	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-alanine 20V, Negative-QTOF	splash10-000i-9200000000-2df5117d1f0498fa4d47	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-alanine 40V, Negative-QTOF	splash10-0076-9000000000-74175a91d6530fa275df	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-alanine 10V, Positive-QTOF	splash10-000l-9100000000-5c3ebb626b607f2771cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-alanine 20V, Positive-QTOF	splash10-006x-9000000000-3526994d54c9aef41949	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-alanine 40V, Positive-QTOF	splash10-0006-9000000000-527b4afd5857c451f463	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	4.00 (1.75-8.27) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	0.5 (0.0-1.0) umol/mmol creatinine	Adult (>18 years old)	Both	Prostate Cancer	19212411	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Prostate cancer
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

Associated OMIM IDs

114500 (Colorectal cancer)
176807 (Prostate cancer)

External Links

DrugBank ID

DB02518

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022231

KNApSAcK ID

Not Available

Chemspider ID

79449

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5733

PubChem Compound

88064

PDB ID

Not Available

ChEBI ID

40992

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Vanzura, Jiri; Kasafirek, Evzen; Hrabalek, Alexandr; Vinsova, Jarmila; Krepelka, Jiri. Process for preparing highly pure N-acetyl-L- or -D-alanine. Czech. (1989), 4 pp.

Material Safety Data Sheet (MSDS)

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. Epub 2006 Jan 18. [PubMed:16465618 ]
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 ]
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 ]
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 ]
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 ]

Enzymes

Enzyme Details

1. Carbamoyl-phosphate synthase [ammonia], mitochondrial

General function:: Involved in catalytic activity
Specific function:: Involved in the urea cycle of ureotelic animals where the enzyme plays an important role in removing excess ammonia from the cell.
Gene Name:: CPS1
Uniprot ID:: P31327
Molecular weight:: 165649.075

Enzyme Details

2. N-acetylglutamate synthase, mitochondrial

General function:: Involved in N-acetyltransferase activity
Specific function:: Plays a role in the regulation of ureagenesis by producing variable amounts of N-acetylglutamate (NAG), thus modulating carbamoylphosphate synthase I (CPSI) activity.
Gene Name:: NAGS
Uniprot ID:: Q8N159
Molecular weight:: 58155.835

Showing metabocard for N-Acetyl-L-alanine (HMDB0000766)

MOL for HMDB0000766 (N-Acetyl-L-alanine)

3D MOL for HMDB0000766 (N-Acetyl-L-alanine)

3D SDF for HMDB0000766 (N-Acetyl-L-alanine)

3D-SDF for HMDB0000766 (N-Acetyl-L-alanine)

PDB for HMDB0000766 (N-Acetyl-L-alanine)

3D PDB for HMDB0000766 (N-Acetyl-L-alanine)

SMILES for HMDB0000766 (N-Acetyl-L-alanine)

INCHI for HMDB0000766 (N-Acetyl-L-alanine)

Structure for HMDB0000766 (N-Acetyl-L-alanine)

3D Structure for HMDB0000766 (N-Acetyl-L-alanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes