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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 07:44:49 UTC
Update Date2021-09-24 07:44:49 UTC
HMDB IDHMDB0304170
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-amino-4-deoxychorismate
Description4-amino-4-deoxychorismate, also known as adc, belongs to dicarboxylic acids and derivatives class of compounds. Those are organic compounds containing exactly two carboxylic acid groups. 4-amino-4-deoxychorismate is soluble (in water) and a weakly acidic compound (based on its pKa). 4-amino-4-deoxychorismate can be found in a number of food items such as chives, narrowleaf cattail, green vegetables, and chicory leaves, which makes 4-amino-4-deoxychorismate a potential biomarker for the consumption of these food products. 4-amino-4-deoxychorismate exists in E.coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
ValueSource
ADCChEBI
4-Amino-4-deoxychorismateGenerator
4-amino-4-Deoxychorismic acidGenerator
Chemical FormulaC10H11NO5
Average Molecular Weight225.198
Monoisotopic Molecular Weight225.063722467
IUPAC Name(3R,4R)-4-amino-3-[(1-carboxyeth-1-en-1-yl)oxy]cyclohexa-1,5-diene-1-carboxylic acid
Traditional Name4-amino-4-deoxychorismic acid
CAS Registry NumberNot Available
SMILES
N[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O
InChI Identifier
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)/t7-,8-/m1/s1
InChI KeyOIUJHGOLFKDBSU-HTQZYQBOSA-N
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic 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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(-2.3) g/LALOGPS
logP10(-2.8) g/LChemAxon
logS10(-1.3) g/LALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)9.12ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.85 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.97 m³·mol⁻¹ChemAxon
Polarizability20.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-amino-4-deoxychorismate,3TMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1N[Si](C)(C)C)C(=O)O[Si](C)(C)C2081.2Semi standard non polar33892256
4-amino-4-deoxychorismate,3TMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1N[Si](C)(C)C)C(=O)O[Si](C)(C)C2067.2Standard non polar33892256
4-amino-4-deoxychorismate,3TMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1N[Si](C)(C)C)C(=O)O[Si](C)(C)C2662.7Standard polar33892256
4-amino-4-deoxychorismate,3TMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2202.5Semi standard non polar33892256
4-amino-4-deoxychorismate,3TMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2120.1Standard non polar33892256
4-amino-4-deoxychorismate,3TMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2850.6Standard polar33892256
4-amino-4-deoxychorismate,3TMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2222.0Semi standard non polar33892256
4-amino-4-deoxychorismate,3TMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2132.3Standard non polar33892256
4-amino-4-deoxychorismate,3TMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2683.1Standard polar33892256
4-amino-4-deoxychorismate,4TMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2211.8Semi standard non polar33892256
4-amino-4-deoxychorismate,4TMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2186.2Standard non polar33892256
4-amino-4-deoxychorismate,4TMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C)C=C[C@H]1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2445.4Standard polar33892256
4-amino-4-deoxychorismate,3TBDMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2714.2Semi standard non polar33892256
4-amino-4-deoxychorismate,3TBDMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2584.1Standard non polar33892256
4-amino-4-deoxychorismate,3TBDMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2908.7Standard polar33892256
4-amino-4-deoxychorismate,3TBDMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2861.6Semi standard non polar33892256
4-amino-4-deoxychorismate,3TBDMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2676.1Standard non polar33892256
4-amino-4-deoxychorismate,3TBDMS,isomer #2C=C(O[C@@H]1C=C(C(=O)O)C=C[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3008.5Standard polar33892256
4-amino-4-deoxychorismate,3TBDMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2853.6Semi standard non polar33892256
4-amino-4-deoxychorismate,3TBDMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2649.5Standard non polar33892256
4-amino-4-deoxychorismate,3TBDMS,isomer #3C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2890.9Standard polar33892256
4-amino-4-deoxychorismate,4TBDMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3067.0Semi standard non polar33892256
4-amino-4-deoxychorismate,4TBDMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2866.2Standard non polar33892256
4-amino-4-deoxychorismate,4TBDMS,isomer #1C=C(O[C@@H]1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2779.8Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030486
KNApSAcK IDC00000730
Chemspider ID391414
KEGG Compound IDC11355
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443142
PDB IDNot Available
ChEBI ID18198
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available