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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:06:09 UTC
Update Date2021-09-26 23:02:41 UTC
HMDB IDHMDB0250945
Secondary Accession NumbersNone
Metabolite Identification
Common NameDehydrochloramphenicol
DescriptionDehydrochloramphenicol, also known as DH-CAP, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review a significant number of articles have been published on Dehydrochloramphenicol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydrochloramphenicol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydrochloramphenicol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
DH-CAPMeSH
Chemical FormulaC11H10Cl2N2O5
Average Molecular Weight321.11
Monoisotopic Molecular Weight319.9966768
IUPAC Name2,2-dichloro-N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide
Traditional Name2,2-dichloro-N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide
CAS Registry NumberNot Available
SMILES
OCC(NC(=O)C(Cl)Cl)C(=O)C1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C11H10Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8,10,16H,5H2,(H,14,18)
InChI KeyZMCQNNUYRHSMAB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Nitrobenzene
  • Nitroaromatic compound
  • Benzoyl
  • Aryl alkyl ketone
  • Monocyclic benzene moiety
  • Beta-hydroxy ketone
  • Benzenoid
  • Carboxamide group
  • C-nitro compound
  • Secondary carboxylic acid amide
  • Organic nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Organic oxoazanium
  • Organic zwitterion
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Alkyl chloride
  • Organonitrogen compound
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Alkyl halide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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 Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(1.1) g/LALOGPS
logP10(1.17) g/LChemAxon
logS10(-3.4) g/LALOGPS
pKa (Strongest Acidic)7.99ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area109.54 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.6 m³·mol⁻¹ChemAxon
Polarizability27.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DehydrochloramphenicolOCC(NC(=O)C(Cl)Cl)C(=O)C1=CC=C(C=C1)[N+]([O-])=O3630.9Standard polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
DehydrochloramphenicolOCC(NC(=O)C(Cl)Cl)C(=O)C1=CC=C(C=C1)[N+]([O-])=O2427.4Standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
DehydrochloramphenicolOCC(NC(=O)C(Cl)Cl)C(=O)C1=CC=C(C=C1)[N+]([O-])=O2505.6Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21134
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22536
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]