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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:21 UTC

HMDB ID

HMDB0000978

Secondary Accession Numbers

HMDB00978

Metabolite Identification

Common Name

4-(2-Aminophenyl)-2,4-dioxobutanoic acid

Description

4-(2-Aminophenyl)-2,4-dioxobutanoic acid, also known as 2-amino-alpha,gamma-dioxobenzenebutanoic acid, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid is a strong basic compound (based on its pKa). 4-(2-Aminophenyl)-2,4-dioxobutanoic acid is a substrate for Kynurenine/alpha-aminoadipate aminotransferase mitochondrial. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid exists in all living species, ranging from bacteria to humans. 4-(2-aminophenyl)-2,4-dioxobutanoic acid and L-glutamic acid can be biosynthesized from L-kynurenine and oxoglutaric acid through the action of the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In humans, 4-(2-aminophenyl)-2,4-dioxobutanoic acid is involved in tryptophan metabolism.

Structure

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

  Mrv1652302102019012D          

 15 15  0  0  0  0            999 V2000
 9999.623010000.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3373 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.053410000.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7673 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.481310000.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7673 9999.1756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.053410001.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.623010001.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.193410001.2380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.907910000.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.193510000.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.478910000.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4789 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1934 9998.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9079 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
  1 10  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000978

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=C(C=CC=C1)C(=O)CC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO4/c11-7-4-2-1-3-6(7)8(12)5-9(13)10(14)15/h1-4H,5,11H2,(H,14,15)

> <INCHI_KEY>
CAOVWYZQMPNAFJ-UHFFFAOYSA-N

> <FORMULA>
C10H9NO4

> <MOLECULAR_WEIGHT>
207.1828

> <EXACT_MASS>
207.053157781

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.32241758340649

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-aminophenyl)-2,4-dioxobutanoic acid

> <ALOGPS_LOGP>
0.91

> <JCHEM_LOGP>
0.9954513136686617

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.780542359456446

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9621909659133543

> <JCHEM_PKA_STRONGEST_BASIC>
3.335078673400071

> <JCHEM_POLAR_SURFACE_AREA>
97.46000000000001

> <JCHEM_REFRACTIVITY>
52.8513

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2-aminophenyl)-2,4-dioxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0    8665.9638667.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.2968666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.6338667.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.9668666.666   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8671.2988667.437   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8669.9668665.128   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8668.6338668.978   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8665.9638668.978   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8663.2948668.978   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8664.6288666.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.2958667.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.9618666.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.9618665.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.2948664.357   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6288665.127   0.000  0.00  0.00           C+0
CONECT    1    2    8   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3                                                            
CONECT    8    1                                                            
CONECT    9   11                                                            
CONECT   10   11   15    1                                                  
CONECT   11   10   12    9                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(2-Aminophenyl)-2,4-dioxobutanoate	ChEBI
4-(2-Aminophenyl)-2,4-dioxo-butanoate	HMDB
4-(2-Aminophenyl)-2,4-dioxo-butanoic acid	HMDB
2-Amino-alpha,gamma-dioxobenzenebutanoic acid	HMDB
2-Amino-α,γ-dioxobenzenebutanoic acid	HMDB
4-(2-Aminophenyl)-2,4-dioxobutanoic acid	HMDB

Chemical Formula

C₁₀H₉NO₄

Average Molecular Weight

207.1828

Monoisotopic Molecular Weight

207.053157781

IUPAC Name

4-(2-aminophenyl)-2,4-dioxobutanoic acid

Traditional Name

4-(2-aminophenyl)-2,4-dioxobutanoic acid

CAS Registry Number

90924-76-8

SMILES

NC1=C(C=CC=C1)C(=O)CC(=O)C(O)=O

InChI Identifier

InChI=1S/C10H9NO4/c11-7-4-2-1-3-6(7)8(12)5-9(13)10(14)15/h1-4H,5,11H2,(H,14,15)

InChI Key

CAOVWYZQMPNAFJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Benzoyl
Gamma-keto acid
Aryl alkyl ketone
Aniline or substituted anilines
1,3-diketone
Monocyclic benzene moiety
Alpha-keto acid
Keto acid
1,3-dicarbonyl compound
Benzenoid
Alpha-hydroxy ketone
Vinylogous amide
Amino acid
Amino acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Primary amine
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

substituted aniline (CHEBI:17442 )
2-oxo monocarboxylic acid (CHEBI:17442 )
aromatic ketone (CHEBI:17442 )
4-oxo monocarboxylic acid (CHEBI:17442 )
dioxo monocarboxylic acid (CHEBI:17442 )
beta-diketone (CHEBI:17442 )

Ontology

Not Available

Feces (PMID: 27786174)

Cellular substructure

Cytoplasm (HMDB: HMDB0000978)

Organelle

Mitochondrion (HMDB: HMDB0000978)

Source

Endogenous

Endogenous (HMDB: HMDB0000978)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0000978)

Role

Not Available

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	0.56 g/L	ALOGPS
logP	0.91	ALOGPS
logP	1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.96	ChemAxon
pKa (Strongest Basic)	3.34	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.85 m³·mol⁻¹	ChemAxon
Polarizability	19.32 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	146.845	31661259
DarkChem	[M-H]-	144.477	31661259
AllCCS	[M+H]+	144.887	32859911
AllCCS	[M-H]-	142.762	32859911
DeepCCS	[M+H]+	144.648	30932474
DeepCCS	[M-H]-	142.29	30932474
DeepCCS	[M-2H]-	177.216	30932474
DeepCCS	[M+Na]+	152.613	30932474
AllCCS	[M+H]+	144.9	32859911
AllCCS	[M+H-H2O]+	140.8	32859911
AllCCS	[M+NH4]+	148.6	32859911
AllCCS	[M+Na]+	149.7	32859911
AllCCS	[M-H]-	142.8	32859911
AllCCS	[M+Na-2H]-	143.1	32859911
AllCCS	[M+HCOO]-	143.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(2-Aminophenyl)-2,4-dioxobutanoic acid	NC1=C(C=CC=C1)C(=O)CC(=O)C(O)=O	3280.2	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid	NC1=C(C=CC=C1)C(=O)CC(=O)C(O)=O	1755.6	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid	NC1=C(C=CC=C1)C(=O)CC(=O)C(O)=O	1965.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CC(=O)C1=CC=CC=C1N	1986.3	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=CC(=O)C1=CC=CC=C1N)C(=O)O	2158.7	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TMS,isomer #3	C[Si](C)(C)NC1=CC=CC=C1C(=O)CC(=O)C(=O)O	2094.6	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N)O[Si](C)(C)C	2136.6	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N)O[Si](C)(C)C	1983.5	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N)O[Si](C)(C)C	2779.1	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1C(=O)CC(=O)C(=O)O[Si](C)(C)C	2079.3	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1C(=O)CC(=O)C(=O)O[Si](C)(C)C	2019.0	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1C(=O)CC(=O)C(=O)O[Si](C)(C)C	2462.1	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #3	C[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C)C(=O)O	2201.5	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #3	C[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C)C(=O)O	2105.4	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #3	C[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C)C(=O)O	2646.2	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #4	C[Si](C)(C)N(C1=CC=CC=C1C(=O)CC(=O)C(=O)O)[Si](C)(C)C	2047.4	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #4	C[Si](C)(C)N(C1=CC=CC=C1C(=O)CC(=O)C(=O)O)[Si](C)(C)C	2151.3	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TMS,isomer #4	C[Si](C)(C)N(C1=CC=CC=C1C(=O)CC(=O)C(=O)O)[Si](C)(C)C	2581.7	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2218.4	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2100.8	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2449.3	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(=O)CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2070.1	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(=O)CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2109.2	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C(=O)CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2288.8	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TMS,isomer #3	C[Si](C)(C)OC(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2187.8	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TMS,isomer #3	C[Si](C)(C)OC(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2246.3	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TMS,isomer #3	C[Si](C)(C)OC(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2493.2	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2204.8	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2195.9	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2299.1	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC(=O)C1=CC=CC=C1N	2242.1	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CC(=O)C1=CC=CC=C1N)C(=O)O	2417.8	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)CC(=O)C(=O)O	2361.4	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N)O[Si](C)(C)C(C)(C)C	2614.6	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N)O[Si](C)(C)C(C)(C)C	2352.9	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N)O[Si](C)(C)C(C)(C)C	2897.1	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)CC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2540.1	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)CC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2478.6	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)CC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2709.4	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2683.6	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2532.4	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2835.2	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)CC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2530.5	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)CC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2533.0	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)CC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2729.0	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2876.0	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2660.7	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2787.6	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2728.4	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2715.1	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2651.1	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2833.3	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2793.6	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2783.0	Standard polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3029.1	Semi standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2870.8	Standard non polar	33892256
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2708.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ml-9600000000-9ee4bc222cfbefcf7167	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-6940000000-0a58537f3d042b452b9a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 10V, Positive-QTOF	splash10-0ab9-0950000000-f6e0367966abff1dc873	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 20V, Positive-QTOF	splash10-00di-0900000000-a2c601ca3bb3e2f03be2	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 40V, Positive-QTOF	splash10-00di-9500000000-7dd33609488e64596836	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 10V, Negative-QTOF	splash10-0a4i-1490000000-82e91d56bdce0e09cb73	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 20V, Negative-QTOF	splash10-08fr-4930000000-4e754ee43c0a1b217738	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 40V, Negative-QTOF	splash10-0006-9400000000-ff4da0a8b66f352cf30d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 10V, Negative-QTOF	splash10-0002-3920000000-ed3ee349719d21882219	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 20V, Negative-QTOF	splash10-0006-9200000000-5a28b87fef7bde9d37c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-5761d11f372a2a30748f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 10V, Positive-QTOF	splash10-08mi-2930000000-680696b189e40364b3e1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 20V, Positive-QTOF	splash10-00di-2900000000-e522d34ea0481d109d3e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Aminophenyl)-2,4-dioxobutanoic acid 40V, Positive-QTOF	splash10-0006-9000000000-ee62e52b5df8d4bab6ff	2021-09-24	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

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Enthesitis-related arthritis	27786174	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022348

KNApSAcK ID

Not Available

Chemspider ID

459

KEGG Compound ID

C01252

BioCyc ID

Not Available

BiGG ID

37199

Wikipedia Link

Not Available

METLIN ID

5916

PubChem Compound

472

PDB ID

Not Available

ChEBI ID

17442

Food Biomarker Ontology

Not Available

VMH ID

4APHDOB

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Reactions

Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic acid	details

Enzyme Details

2. Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro).
Gene Name:: AADAT
Uniprot ID:: Q8N5Z0
Molecular weight:: 47351.17

Reactions

Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic acid	details

Enzyme Details

3. Kynurenine--oxoglutarate transaminase 1

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:: CCBL1
Uniprot ID:: Q16773
Molecular weight:: 47874.765

Reactions

Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic acid	details

Enzyme Details

4. Aminoadipate aminotransferase, isoform CRA_b

General function:: Transcription
Specific function:: Not Available
Gene Name:: AADAT
Uniprot ID:: Q4W5N8
Molecular weight:: 47351.2

Enzyme Details

5. Kynurenine--oxoglutarate transaminase 3

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:: CCBL2
Uniprot ID:: Q6YP21
Molecular weight:: 51399.855

Reactions

Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic acid	details
Kynurenine + Glyoxylic acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glycine	details

Showing metabocard for 4-(2-Aminophenyl)-2,4-dioxobutanoic acid (HMDB0000978)

MOL for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

3D MOL for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

3D SDF for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

3D-SDF for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

PDB for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

3D PDB for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

SMILES for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

INCHI for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

Structure for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

3D Structure for HMDB0000978 (4-(2-Aminophenyl)-2,4-dioxobutanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions