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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

HMDB0001138

Secondary Accession Numbers

HMDB01138

Metabolite Identification

Common Name

N-Acetyl-L-glutamic acid

Description

N-Acetyl-L-glutamic acid or N-Acetylglutamate, 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-glutamate can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-glutamate is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-glutamic acid. N-Acetyl-L-glutamic acid is found in all organisms ranging from bacteria to plants to animals. 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-acetylglutamate 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 glutamic acid can also occur. In particular, N-Acetyl-L-glutamic acid can be biosynthesized from glutamate and acetylornithine by ornithine acetyltransferase, and from glutamic acid and acetyl-CoA by the enzyme known as N-acetylglutamate synthase. N-Acetyl-L-glutamic acid is the first intermediate involved in the biosynthesis of arginine in prokaryotes and simple eukaryotes and a regulator of the urea cycle in vertebrates. In vertebrates, N-acetylglutamic acid is the allosteric activator molecule to mitochondrial carbamyl phosphate synthetase I (CPSI) which is the first enzyme in the urea cycle. It triggers the production of the first urea cycle intermediate, a compound known as carbamyl phosphate. Notably the CPSI enzyme is inactive when N-acetylglutamic acid is not present. A deficiency in N-acetyl glutamate synthase or a genetic mutation in the gene coding for the enzyme will lead to urea cycle failure in which ammonia is not converted to urea, but rather accumulated in the blood leading to the condition called Type I hyperammonemia. 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 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

  Mrv1652309042000182D          

 13 12  0  0  0  0            999 V2000
10000.728110000.4124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.013610000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299310000.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585010000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.870710000.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585010001.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7281 9999.5886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.4437 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1592 9999.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4437 9998.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.443710000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.159210000.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.443710001.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  1  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001138

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)N[C@@H](CCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1

> <INCHI_KEY>
RFMMMVDNIPUKGG-YFKPBYRVSA-N

> <FORMULA>
C7H11NO5

> <MOLECULAR_WEIGHT>
189.1659

> <EXACT_MASS>
189.063722467

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.440299050547086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-acetamidopentanedioic acid

> <ALOGPS_LOGP>
-0.67

> <JCHEM_LOGP>
-1.1130154166666664

> <ALOGPS_LOGS>
-1.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.288470351468538

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.432014588807448

> <JCHEM_PKA_STRONGEST_BASIC>
-1.800828671223234

> <JCHEM_POLAR_SURFACE_AREA>
103.70000000000002

> <JCHEM_REFRACTIVITY>
40.731500000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-L-glutamate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.0268667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.6928668.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.3598667.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.0258668.206   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8662.6928667.436   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8664.0258669.746   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8668.0268665.899   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8669.3628665.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8670.6978665.899   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8669.3628663.587   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8669.3628668.206   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8670.6978667.436   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8669.3628669.746   0.000  0.00  0.00           O+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-2-(Acetylamino)pentanedioic acid	ChEBI
Ac-glu-OH	ChEBI
Acetyl-L-glutamic acid	ChEBI
Acetylglutamic acid	ChEBI
L-N-Acetylglutamic acid	ChEBI
N-Ac-glu-OH	ChEBI
N-ACETYL-L-glutamATE	ChEBI
N-Acetylglutamic acid	ChEBI
(S)-2-(Acetylamino)pentanedioate	Generator
Acetyl-L-glutamate	Generator
Acetylglutamate	Generator
L-N-Acetylglutamate	Generator
N-Acetylglutamate	Generator
N-Acetylglutamic acid semialdehyde	HMDB
N-Acetylglutamate, potassium salt, (L)-isomer	HMDB
N-Acetylglutamate, (D)-isomer	HMDB
N-Acetylglutamate, calcium salt (1:1), (L)-isomer	HMDB
N-Acetylglutamate, dipotassium salt, (L)-isomer	HMDB
N-Acetylglutamate, disodium salt, (L)-isomer	HMDB
N-Acetylglutamate, calcium salt, (L)-isomer	HMDB
N-Acetylglutamate, magnesium salt, (L)-isomer	HMDB
Sodium N-acetylglutamate	HMDB
N-Acetylglutamate, (DL)-isomer	HMDB
N-Acetylglutamate, monosodium salt, (L)-isomer	HMDB
N-Acetyl-L-glutaminic acid	HMDB
alpha-(N-Acetyl)-L-glutamic acid	HMDB
Α-(N-acetyl)-L-glutamic acid	HMDB
NAcGlu	HMDB
N-Acetyl-L-glutamic acid	Generator, KEGG

Chemical Formula

C₇H₁₁NO₅

Average Molecular Weight

189.1659

Monoisotopic Molecular Weight

189.063722467

IUPAC Name

(2S)-2-acetamidopentanedioic acid

Traditional Name

N-acetyl-L-glutamate

CAS Registry Number

1188-37-0

SMILES

CC(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1

InChI Key

RFMMMVDNIPUKGG-YFKPBYRVSA-N

Chemical Taxonomy

Description

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

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Dicarboxylic acid or derivatives
Fatty acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:17533 )
N-acyl-L-glutamic acid (CHEBI:17533 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)
Saliva (HMDB: HMDB0001138)

Organ

Liver (HMDB: HMDB0001138)
Placenta (HMDB: HMDB0001138)

Excreta

Biofluid or Excreta

Urine (PMID: 19212411)
Feces (PMID: 22411374)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001138)

Source

Exogenous

Exogenous (HMDB: HMDB0001138)

Endogenous

Endogenous (HMDB: HMDB0001138)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arginine Metabolism (PathBank: SMP0002416)
Proline Metabolism (PathBank: SMP0002420)
Ornithine Metabolism (PathBank: SMP0121275)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	199 - 201 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	52 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	139.633	30932474
[M+H]+	Baker	139.033	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	18.6 g/L	ALOGPS
logP	-0.67	ALOGPS
logP	-1.1	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.73 m³·mol⁻¹	ChemAxon
Polarizability	17.44 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
DeepCCS	[M+H]+	135.361	30932474
DeepCCS	[M-H]-	132.506	30932474
DeepCCS	[M-2H]-	168.962	30932474
DeepCCS	[M+Na]+	144.5	30932474
AllCCS	[M+H]+	142.7	32859911
AllCCS	[M+H-H2O]+	139.0	32859911
AllCCS	[M+NH4]+	146.2	32859911
AllCCS	[M+Na]+	147.2	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	139.0	32859911
AllCCS	[M+HCOO]-	140.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-glutamic acid	CC(=O)N[C@@H](CCC(O)=O)C(O)=O	2821.6	Standard polar	33892256
N-Acetyl-L-glutamic acid	CC(=O)N[C@@H](CCC(O)=O)C(O)=O	1512.2	Standard non polar	33892256
N-Acetyl-L-glutamic acid	CC(=O)N[C@@H](CCC(O)=O)C(O)=O	1800.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-glutamic acid,1TMS,isomer #1	CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O	1686.0	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,1TMS,isomer #2	CC(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C	1682.9	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,1TMS,isomer #3	CC(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C	1721.4	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,2TMS,isomer #1	CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1768.4	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,2TMS,isomer #2	CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1753.0	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,2TMS,isomer #3	CC(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1763.0	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,3TMS,isomer #1	CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1783.2	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,3TMS,isomer #1	CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1808.1	Standard non polar	33892256
N-Acetyl-L-glutamic acid,3TMS,isomer #1	CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1974.4	Standard polar	33892256
N-Acetyl-L-glutamic acid,1TBDMS,isomer #1	CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1937.7	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,1TBDMS,isomer #2	CC(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1926.9	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,1TBDMS,isomer #3	CC(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	1947.4	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,2TBDMS,isomer #1	CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2201.0	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,2TBDMS,isomer #2	CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2231.6	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,2TBDMS,isomer #3	CC(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2207.0	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,3TBDMS,isomer #1	CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2444.6	Semi standard non polar	33892256
N-Acetyl-L-glutamic acid,3TBDMS,isomer #1	CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2427.1	Standard non polar	33892256
N-Acetyl-L-glutamic acid,3TBDMS,isomer #1	CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2392.3	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-glutamic acid GC-MS (3 TMS)	splash10-0a4i-1940000000-78ee4843d1eab79c7ca3	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-glutamic acid GC-MS (2 TMS)	splash10-0api-3930000000-e499004b087e5d741b02	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-glutamic acid GC-EI-TOF (Non-derivatized)	splash10-0a4j-0920000000-2d39b0eff0ff23756843	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-glutamic acid GC-EI-TOF (Non-derivatized)	splash10-0aor-1920000000-a2fe62d19e50f9db103f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-glutamic acid GC-EI-TOF (Non-derivatized)	splash10-0a4j-0920000000-546571923f012476b58b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-glutamic acid GC-EI-TOF (Non-derivatized)	splash10-0ap0-1910000000-d18f7c4035b189c1f4b6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-glutamic acid GC-EI-TOF (Non-derivatized)	splash10-0a4r-1900000000-fc8347700abd012bf349	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-glutamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-cdb488a97c5bf1952810	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-glutamic acid 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-glutamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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-glutamic acid LC-ESI-QQ , negative-QTOF	splash10-000i-0900000000-1f9f80a37aa4e37ee878	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid LC-ESI-QQ , negative-QTOF	splash10-0fb9-0900000000-5423b76f7eb4b2a17fac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid LC-ESI-QQ , negative-QTOF	splash10-0udi-2900000000-38410c884a2999611065	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid LC-ESI-QQ , negative-QTOF	splash10-0zfr-9700000000-85acd9611312dd7df0db	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid LC-ESI-QQ , negative-QTOF	splash10-0pb9-9100000000-0d780e23d772cf133da2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid , negative-QTOF	splash10-0ufr-1900000000-7a57de84cf9c6671cfc2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid LC-ESI-QQ , positive-QTOF	splash10-0006-0900000000-7b58c7204405ece93fca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid LC-ESI-QQ , positive-QTOF	splash10-001i-1900000000-515b33cc5674fc8985c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid LC-ESI-QQ , positive-QTOF	splash10-001i-9300000000-b379a6e4d794e810c478	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid LC-ESI-QQ , positive-QTOF	splash10-001i-9000000000-2ce098bb9e1b35433878	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid LC-ESI-QQ , positive-QTOF	splash10-001i-9000000000-8e7d8abde262b7d5cb45	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid , positive-QTOF	splash10-001i-1900000000-a3bdc3627857c5f47f4b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 10V, Negative-QTOF	splash10-0ufr-2900000000-b074eaccd0b3864766b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 35V, Negative-QTOF	splash10-0fb9-0900000000-54faa7b7182f5cceca84	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 10V, Positive-QTOF	splash10-001i-6900000000-0f14d0a7c8fb67a381b2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 30V, Positive-QTOF	splash10-053r-9000000000-333b6aa44450dbd0c754	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 20V, Positive-QTOF	splash10-001i-9100000000-adf2d3645b4231cbddc3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 10V, Positive-QTOF	splash10-001i-2900000000-d7df112ff7af7e076d70	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 40V, Positive-QTOF	splash10-0536-9000000000-d70c37086adaa1636750	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 10V, Positive-QTOF	splash10-006x-0900000000-88345aaf9776c7fb8676	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 20V, Positive-QTOF	splash10-0udl-2900000000-5fca3bd987ebf6b42946	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 40V, Positive-QTOF	splash10-0udj-9500000000-be58124b136b37456414	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 10V, Negative-QTOF	splash10-000i-0900000000-a56ffb8d475d132443a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 20V, Negative-QTOF	splash10-004v-2900000000-c32612499c0a2ceb8298	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamic acid 40V, Negative-QTOF	splash10-052f-9300000000-75dbbc130d00cfec5880	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2019-03-11	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

Mitochondria

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Liver
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	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)	Not Specified	Normal	25985090	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27065191	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	0.0448 +/- 0.0564 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.0695 +/- 0.137 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.0700 +/- 0.0525 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.0723 +/- 0.0367 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	0-42 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details
Urine	Detected and Quantified	6.515 +/- 4.434 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	3.47 (2.78-4.83) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28157703	details
Urine	Detected and Quantified	1 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21388201	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cryptosporidium infection	22944170	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	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	26.305 +/- 30.916 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	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
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 ] 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 ] 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 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
176807 (Prostate cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB04075

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031019

KNApSAcK ID

Not Available

Chemspider ID

64077

KEGG Compound ID

C00624

BioCyc ID

ACETYL-GLU

BiGG ID

Not Available

Wikipedia Link

N-Acetylglutamic_acid

METLIN ID

Not Available

PubChem Compound

70914

PDB ID

Not Available

ChEBI ID

17533

Food Biomarker Ontology

Not Available

VMH ID

ACGLU

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng. Preparation of N-acetyl-L-glutamic acid. Huaxue Shijie (2002), 43(7), 363-365.

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 ]
Zhang W, Holzknecht RA, Butkowski RJ, Tuchman M: Immunochemical analysis of carbamyl phosphate synthetase I and ornithine transcarbamylase deficient livers: elevated N-acetylglutamate level in a liver lacking carbamyl phosphate synthetase protein. Clin Invest Med. 1990 Aug;13(4):183-8. [PubMed:2208834 ]
Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. [PubMed:7952062 ]
Tuchman M, Holzknecht RA: N-acetylglutamate content in liver and gut of normal and fasted mice, normal human livers, and livers of individuals with carbamyl phosphate synthetase or ornithine transcarbamylase deficiency. Pediatr Res. 1990 Apr;27(4 Pt 1):408-12. [PubMed:2342831 ]
Vockley J, Vockley CM, Lin SP, Tuchman M, Wu TC, Lin CY, Seashore MR: Normal N-acetylglutamate concentration measured in liver from a new patient with N-acetylglutamate synthetase deficiency: physiologic and biochemical implications. Biochem Med Metab Biol. 1992 Feb;47(1):38-46. [PubMed:1562355 ]
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

Reactions

Acetyl-CoA + Glutamic acid → Coenzyme A + N-Acetyl-L-glutamic acid	details

Showing metabocard for N-Acetyl-L-glutamic acid (HMDB0001138)

MOL for HMDB0001138 (N-Acetyl-L-glutamic acid)

3D MOL for HMDB0001138 (N-Acetyl-L-glutamic acid)

3D SDF for HMDB0001138 (N-Acetyl-L-glutamic acid)

3D-SDF for HMDB0001138 (N-Acetyl-L-glutamic acid)

PDB for HMDB0001138 (N-Acetyl-L-glutamic acid)

3D PDB for HMDB0001138 (N-Acetyl-L-glutamic acid)

SMILES for HMDB0001138 (N-Acetyl-L-glutamic acid)

INCHI for HMDB0001138 (N-Acetyl-L-glutamic acid)

Structure for HMDB0001138 (N-Acetyl-L-glutamic acid)

3D Structure for HMDB0001138 (N-Acetyl-L-glutamic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions