Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000933
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 Pseudomonas aeruginosa, 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)
  • 4-Amino-4-deoxychorismic acid
  • ADC
  • ADCA
Chemical Formula: C10H10NO5
Average Molecular Weight: 224.193
Monoisotopic Molecular Weight: 224.056446006
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
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct Parent Dicarboxylic acids and derivatives
Alternative Parents
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility11.6 mg/mLALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)9.12ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.85 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.97 m3·mol-1ChemAxon
Polarizability20.91 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0490000000-747c71d91f7fec4424f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5i-2920000000-6f27cefa2288efacad44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-7900000000-6116e108334e57aca402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1590000000-d6e2a54c8e44b1b75d85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0r7i-0930000000-0e8cf668b969fac1793bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0nmr-2900000000-f1c52f522ed17c4feb67View in MoNA
  • 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
External Links:
HMDB IDNot Available
Pubchem Compound ID443142
Kegg IDC11355
ChemSpider ID391414
Wikipedia IDNot Available