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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:37 UTC

HMDB ID

HMDB0001330

Secondary Accession Numbers

HMDB0062578
HMDB01330
HMDB62578

Metabolite Identification

Common Name

2-Amino-3-carboxymuconic acid semialdehyde

Description

2-Amino-3-carboxymuconic acid semialdehyde (CAS: 16597-58-3) is an intermediate metabolite of the tryptophan-niacin catabolic pathway. Current interest in the degradation of tryptophan is mostly due to the role of quinolinate and other metabolites in several neuropathological conditions. Quinolinate is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic acid semialdehyde is enzymatically converted into 2-aminomuconate via 2-aminomuconic semialdehyde (PMID: 10510494 , 16267312 , 14275129 ).

Structure

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

  Mrv1652306071900212D          

 13 12  0  0  0  0            999 V2000
    0.7749   -1.3318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7749   -0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894   -0.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894    0.7307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038   -0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0604   -0.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0604    0.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6540    1.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685    0.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0830    1.1432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6540   -0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6540   -1.3318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -0.0943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001330

> <DATABASE_NAME>
hmdb

> <SMILES>
N\C(C(O)=O)=C(\C=C/C=O)/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)/b2-1-,5-4-

> <INCHI_KEY>
KACPVQQHDVBVFC-OIFXTYEKSA-N

> <FORMULA>
C7H7NO5

> <MOLECULAR_WEIGHT>
185.1342

> <EXACT_MASS>
185.032422339

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.748959169406088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid

> <ALOGPS_LOGP>
-0.05

> <JCHEM_LOGP>
-3.668506936230873

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.4453592131045285

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3791525915700023

> <JCHEM_PKA_STRONGEST_BASIC>
6.720078986530109

> <JCHEM_POLAR_SURFACE_AREA>
117.69

> <JCHEM_REFRACTIVITY>
43.624300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUN-19         0                                  
HETATM    1  N   UNK     0       1.446  -2.486   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.446  -0.946   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.780  -0.176   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.780   1.364   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.114  -0.946   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.113  -0.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.113   1.364   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.221   2.134   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.555   1.364   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.888   2.134   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.221  -0.946   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.221  -2.486   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.555  -0.176   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   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 Stereo Labels

Synonyms

Value	Source
2-Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate	ChEBI
2-Amino-3-(3-oxoprop-1-enyl)-but-2-enedioate	ChEBI
2-Amino-3-carboxymuconate semialdehyde	ChEBI
2-Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid	Generator
2-Amino-3-(3-oxoprop-1-enyl)-but-2-enedioic acid	Generator
2-Amino-3-carboxymuconate-6-semialdehyde	HMDB
ACS	HMDB
Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate	HMDB
Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid	HMDB

Chemical Formula

C₇H₇NO₅

Average Molecular Weight

185.1342

Monoisotopic Molecular Weight

185.032422339

IUPAC Name

(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid

Traditional Name

(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid

CAS Registry Number

16597-19-6

SMILES

N\C(C(O)=O)=C(\C=C/C=O)/C(O)=O

InChI Identifier

InChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)/b2-1-,5-4-

InChI Key

KACPVQQHDVBVFC-OIFXTYEKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Branched fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acid
Fatty acyl
Vinylogous amide
Alpha,beta-unsaturated aldehyde
Enal
Amino acid
Carboxylic acid
Enamine
Organic oxide
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Aldehyde
Primary amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-amino-3-(3-oxoprop-1-enyl)but-2-enedioic acid (CHEBI:995 )

Ontology

Not Available

Cellular substructure

Cytoplasm (HMDB: HMDB0001330)

Source

Endogenous

Endogenous (HMDB: HMDB0001330)

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)
NAD Metabolism (PathBank: SMP0002338)
2-Amino-3-Carboxymuconate Semialdehyde Degradation (PathBank: SMP0121131)

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	1.64 g/L	ALOGPS
logP	-0.05	ALOGPS
logP	-3.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	6.72	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.62 m³·mol⁻¹	ChemAxon
Polarizability	15.75 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
AllCCS	[M+H]+	140.383	32859911
AllCCS	[M-H]-	132.847	32859911
DeepCCS	[M+H]+	135.54	30932474
DeepCCS	[M-H]-	133.104	30932474
DeepCCS	[M-2H]-	168.426	30932474
DeepCCS	[M+Na]+	143.434	30932474
AllCCS	[M+H]+	140.4	32859911
AllCCS	[M+H-H2O]+	136.5	32859911
AllCCS	[M+NH4]+	144.0	32859911
AllCCS	[M+Na]+	145.0	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	133.9	32859911
AllCCS	[M+HCOO]-	135.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Amino-3-carboxymuconic acid semialdehyde	N\C(C(O)=O)=C(\C=C/C=O)/C(O)=O	2778.5	Standard polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde	N\C(C(O)=O)=C(\C=C/C=O)/C(O)=O	1439.9	Standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde	N\C(C(O)=O)=C(\C=C/C=O)/C(O)=O	2016.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Amino-3-carboxymuconic acid semialdehyde,1TMS,isomer #1	C[Si](C)(C)OC(=O)/C(N)=C(\C=C/C=O)C(=O)O	1920.2	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(/C=C\C=O)=C(\N)C(=O)O	1930.5	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,1TMS,isomer #3	C[Si](C)(C)N/C(C(=O)O)=C(/C=C\C=O)C(=O)O	1926.1	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C(N)=C(\C=C/C=O)C(=O)O[Si](C)(C)C	1947.8	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,2TMS,isomer #2	C[Si](C)(C)N/C(C(=O)O[Si](C)(C)C)=C(/C=C\C=O)C(=O)O	2005.1	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,2TMS,isomer #3	C[Si](C)(C)N/C(C(=O)O)=C(/C=C\C=O)C(=O)O[Si](C)(C)C	1981.3	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,2TMS,isomer #4	C[Si](C)(C)N(/C(C(=O)O)=C(/C=C\C=O)C(=O)O)[Si](C)(C)C	2088.2	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TMS,isomer #1	C[Si](C)(C)N/C(C(=O)O[Si](C)(C)C)=C(/C=C\C=O)C(=O)O[Si](C)(C)C	2006.3	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TMS,isomer #1	C[Si](C)(C)N/C(C(=O)O[Si](C)(C)C)=C(/C=C\C=O)C(=O)O[Si](C)(C)C	1908.9	Standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TMS,isomer #1	C[Si](C)(C)N/C(C(=O)O[Si](C)(C)C)=C(/C=C\C=O)C(=O)O[Si](C)(C)C	2467.1	Standard polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TMS,isomer #2	C[Si](C)(C)OC(=O)/C(=C(\C=C/C=O)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2107.3	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TMS,isomer #2	C[Si](C)(C)OC(=O)/C(=C(\C=C/C=O)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1928.5	Standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TMS,isomer #2	C[Si](C)(C)OC(=O)/C(=C(\C=C/C=O)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2344.1	Standard polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2079.7	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1871.0	Standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2265.8	Standard polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2097.8	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1953.5	Standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2063.1	Standard polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C(N)=C(\C=C/C=O)C(=O)O	2158.8	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(/C=C\C=O)=C(\N)C(=O)O	2166.8	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N/C(C(=O)O)=C(/C=C\C=O)C(=O)O	2182.7	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C(N)=C(\C=C/C=O)C(=O)O[Si](C)(C)C(C)(C)C	2377.1	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(/C=C\C=O)C(=O)O	2453.0	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N/C(C(=O)O)=C(/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C	2472.1	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(/C(C(=O)O)=C(/C=C\C=O)C(=O)O)[Si](C)(C)C(C)(C)C	2534.3	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C	2651.2	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C	2559.3	Standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N/C(C(=O)O[Si](C)(C)C(C)(C)C)=C(/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C	2666.8	Standard polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C(=C(\C=C/C=O)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2767.7	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C(=C(\C=C/C=O)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2558.5	Standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C(=C(\C=C/C=O)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2576.8	Standard polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2755.0	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2497.0	Standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2514.7	Standard polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2941.0	Semi standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2717.0	Standard non polar	33892256
2-Amino-3-carboxymuconic acid semialdehyde,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(/C=C\C=O)=C(/C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2450.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-4900000000-62ebd57b1dadb165bc36	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde GC-MS (2 TMS) - 70eV, Positive	splash10-0300-8793000000-3b592a4ef216b8fdf12e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 10V, Positive-QTOF	splash10-00r6-0900000000-0a2ef2dbb21b597d6fc4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 20V, Positive-QTOF	splash10-00dl-4900000000-53b3810106e9c56f7d0a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 40V, Positive-QTOF	splash10-014l-9100000000-fa0ffd8141b90a020246	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 10V, Negative-QTOF	splash10-00ec-1900000000-590832d218cda44b13f8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 20V, Negative-QTOF	splash10-0229-5900000000-74f5fb374736aa527071	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 40V, Negative-QTOF	splash10-00dl-9300000000-84211b6b70277d6fb146	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 10V, Negative-QTOF	splash10-0006-5900000000-210673f89c9ac4437575	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 20V, Negative-QTOF	splash10-01oy-8900000000-1eabc10d32130d827b37	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 40V, Negative-QTOF	splash10-014i-9200000000-3900709db9f9f0db1c3b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 10V, Positive-QTOF	splash10-00kf-0900000000-1ac99f0053d2cc748f29	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 20V, Positive-QTOF	splash10-03kc-2900000000-f5ecf269380d030c89a9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Amino-3-carboxymuconic acid semialdehyde 40V, Positive-QTOF	splash10-066u-9100000000-df3d348bf5ff10948d70	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

Not Available

Tissue Locations

Brain
Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB022559

KNApSAcK ID

Not Available

Chemspider ID

4444266

KEGG Compound ID

C04409

BioCyc ID

Not Available

BiGG ID

1445617

Wikipedia Link

Not Available

METLIN ID

6165

PubChem Compound

5280673

PDB ID

Not Available

ChEBI ID

995

Food Biomarker Ontology

Not Available

VMH ID

CMUSA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ftukijwatari T, Murakami M, Ohta M, Kimura N, Jin-No Y, Sasaki R, Shibata K: Changes in the urinary excretion of the metabolites of the tryptophan-niacin pathway during pregnancy in Japanese women and rats. J Nutr Sci Vitaminol (Tokyo). 2004 Dec;50(6):392-8. [PubMed:15895513 ]
He Z, Spain J: Preparation of 2-aminomuconate from 2-aminophenol by coupled enzymatic dioxygenation and dehydrogenation reactions. J Ind Microbiol Biotechnol. 1999 Aug;23(2):138-142. [PubMed:10510494 ]
NISHIZUKA Y, ICHIYAMA A, GHOLSON RK, HAYAISHI O: STUDIES ON THE METABOLISM OF THE BENZENE RING OF TRYPTOPHAN IN MAMMALIAN TISSUES. I. ENZYMIC FORMATION OF GLUTARIC ACID FROM 3-HYDROXYANTHRANILIC ACID. J Biol Chem. 1965 Feb;240:733-9. [PubMed:14275129 ]
Colabroy KL, Begley TP: Tryptophan catabolism: identification and characterization of a new degradative pathway. J Bacteriol. 2005 Nov;187(22):7866-9. [PubMed:16267312 ]

Enzymes

Enzyme Details

1. 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase

General function:: Involved in catalytic activity
Specific function:: Converts alpha-amino-beta-carboxymuconate-epsilon-semialdehyde (ACMS) to alpha-aminomuconate semialdehyde (AMS). ACMS can be converted non-enzymatically to quinolate (QA), a key precursor of NAD, and a potent endogenous excitotoxin of neuronal cells which is implicated in the pathogenesis of various neurodegenerative disorders. In the presence of ACMSD, ACMS is converted to AMS, a benign catabolite. ACMSD ultimately controls the metabolic fate of tryptophan catabolism along the kynurenine pathway.
Gene Name:: ACMSD
Uniprot ID:: Q8TDX5
Molecular weight:: 38035.045

Reactions

2-Amino-3-carboxymuconic acid semialdehyde → 2-Aminomuconic acid semialdehyde + CO(2)	details
2-Amino-3-carboxymuconic acid semialdehyde → 2-Aminomuconic acid semialdehyde + Carbon dioxide	details

Enzyme Details

2. 3-hydroxyanthranilate 3,4-dioxygenase

General function:: Involved in 3-hydroxyanthranilate 3,4-dioxygenase activity
Specific function:: Catalyzes the oxidative ring opening of 3-hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate.
Gene Name:: HAAO
Uniprot ID:: P46952
Molecular weight:: 32555.935

Reactions

3-Hydroxyanthranilic acid + Oxygen → 2-Amino-3-carboxymuconic acid semialdehyde	details

Showing metabocard for 2-Amino-3-carboxymuconic acid semialdehyde (HMDB0001330)

MOL for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

3D MOL for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

3D SDF for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

3D-SDF for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

PDB for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

3D PDB for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

SMILES for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

INCHI for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

Structure for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

3D Structure for HMDB0001330 (2-Amino-3-carboxymuconic acid semialdehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions

Reactions