ECMDB: 4-Amino-4-deoxychorismate (ECMDB20085) (M2MDB000933)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (558)

Record Information

Version

2.0

Creation Date

2012-05-31 14:26:38 -0600

Update Date

2015-09-17 15:41:54 -0600

Secondary Accession Numbers

ECMDB20085

Identification

Name:

4-Amino-4-deoxychorismate

Description

4-amino-4-deoxychorismate (or ADC) can be classified as a member of the Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups. ADC is involved in antibiotic biosynthesis. In some antibiotic producers, p-aminobenzoic acid (PABA) or its immediate precursor, 4-amino-4-deoxychorismate (ADC), is involved in primary metabolism and antibiotic biosynthesis. (PMID 19389784) In Escherichia coli, the production of PABA is catalyzed by the PabC protein, a beta-lyase that converts 4-amino-4-deoxychorismate (ADC)--the reaction product of the PabA and PabB enzymes--to PABA and pyruvate. (PMID 15500462) 4-Amino-4-deoxychorismate lyase (ADCL) is a member of the fold-type IV of PLP dependent enzymes that converts 4-amino-4-deoxychorismate (ADC) to p-aminobenzoate and pyruvate. (PMID 10876155)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

4-Amino-4-deoxychorismic acid
ADC
ADCA

Chemical Formula:

C₁₀H₁₀NO₅

Weight:

Average: 224.193
Monoisotopic: 224.056446006

InChI Key:

OIUJHGOLFKDBSU-HTQZYQBOSA-M

InChI:

InChI=1S/C10H11NO5/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8H,1,11H2,(H,12,13)(H,14,15)/p-1/t7-,8-/m1/s1

CAS number:

133442-18-9

IUPAC Name:

(3R,4R)-4-amino-3-[(1-carboxyeth-1-en-1-yl)oxy]cyclohexa-1,5-diene-1-carboxylic acid

Traditional IUPAC Name:

4-amino-4-deoxychorismic acid

SMILES:

[H][C@@]1(N)C=CC(=C[C@@]1([H])OC(=C)C([O-])=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Amino acid or derivatives
Amino acid
Carboxylic acid
Amine
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:18198 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-2.8	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	9.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.85 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.97 m³·mol⁻¹	ChemAxon
Polarizability	20.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Folate biosynthesis

PW000908

KEGG Pathways:

Folate biosynthesis ec00790

EcoCyc Pathways:

p-aminobenzoate biosynthesis PWY-6543

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-8910000000-c8513b8f7768e6f33efc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0490000000-747c71d91f7fec4424f5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5i-2920000000-6f27cefa2288efacad44	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-7900000000-6116e108334e57aca402	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1590000000-d6e2a54c8e44b1b75d85	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0r7i-0930000000-0e8cf668b969fac1793b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0nmr-2900000000-f1c52f522ed17c4feb67	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-230aeda7aef66c877ab4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007c-5900000000-768f8cbcb807b9e6947e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-9100000000-2a70d8b0dcb555fda628	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f83-2900000000-b5f4d3f34bb6536a3ab2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01qi-1900000000-a86a6c08b74e46f59e32	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01pc-3900000000-d5faf3cf20848c28d835	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Basset, G. J., Ravanel, S., Quinlivan, E. P., White, R., Giovannoni, J. J., Rebeille, F., Nichols, B. P., Shinozaki, K., Seki, M., Gregory, J. F. 3rd, Hanson, A. D. (2004). "Folate synthesis in plants: the last step of the p-aminobenzoate branch is catalyzed by a plastidial aminodeoxychorismate lyase." Plant J 40:453-461. Pubmed: 15500462
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Zhang, Y., Bai, L., Deng, Z. (2009). "Functional characterization of the first two actinomycete 4-amino-4-deoxychorismate lyase genes." Microbiology 155:2450-2459. Pubmed: 19389784

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	35181
HMDB ID	HMDB0304170
Pubchem Compound ID	443142
Kegg ID	C11355
ChemSpider ID	391414
Wikipedia ID	Not Available
BioCyc ID	4-AMINO-4-DEOXYCHORISMATE
EcoCyc ID	4-AMINO-4-DEOXYCHORISMATE

Enzymes

Protein Details

1. Para-aminobenzoate synthase glutamine amidotransferase component II

General function:: Involved in metabolic process
Specific function:: Catalyzes the biosynthesis of 4-amino-4-deoxychorismate (ADC) from chorismate and glutamine
Gene Name:: pabA
Uniprot ID:: P00903
Molecular weight:: 20772

Reactions

Chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate.

Protein Details

2. Para-aminobenzoate synthase component 1

General function:: Involved in biosynthetic process
Specific function:: Catalyzes the biosynthesis of 4-amino-4-deoxychorismate (ADC) from chorismate and glutamine
Gene Name:: pabB
Uniprot ID:: P05041
Molecular weight:: 50969

Reactions

Chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate.

Protein Details

3. Aminodeoxychorismate lyase

General function:: Involved in 4-amino-4-deoxychorismate lyase activity
Specific function:: Converts 4-amino-4-deoxychorismate into 4-aminobenzoate (PABA) and pyruvate
Gene Name:: pabC
Uniprot ID:: P28305
Molecular weight:: 29715

Reactions

4-amino-4-deoxychorismate = 4-aminobenzoate + pyruvate.

4-Amino-4-deoxychorismate (ECMDB20085) (M2MDB000933)

Structure for #<Compound:0x99ebbdd0>

Enzymes

Reactions

Reactions

Reactions