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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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xad05ca8c> Close
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	Amino acids Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
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 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 55.97 m³·mol⁻¹ ChemAxon Polarizability 20.91 ų 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:	Chorismate + L-Glutamine <> 4-Amino-4-deoxychorismate + L-Glutamate 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acid 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Pyruvic acid Chorismate + L-Glutamine > 4-Amino-4-deoxychorismate + L-Glutamate 4-Amino-4-deoxychorismate > p-Aminobenzoic acid + Pyruvic acid 4-amino-4-deoxychorismate + 4-Amino-4-deoxychorismate > Pyruvic acid + Hydrogen ion + p-Aminobenzoic acid Chorismate + L-Glutamine > L-Glutamic acid + 4-amino-4-deoxychorismate + L-Glutamate + 4-Amino-4-deoxychorismate Chorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-Glutamate 4 4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acid Chorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-Glutamate
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