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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:07:28 UTC
Update Date2021-10-01 21:19:19 UTC
HMDB IDHMDB0250966
Secondary Accession NumbersNone
Metabolite Identification
Common NameDelamanid
Description1-[4-({2-methyl-6-nitro-2H,3H-imidazo[2,1-b][1,3]oxazol-2-yl}methoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidine belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group. Based on a literature review very few articles have been published on 1-[4-({2-methyl-6-nitro-2H,3H-imidazo[2,1-b][1,3]oxazol-2-yl}methoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Delamanid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Delamanid 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
SynonymsNot Available
Chemical FormulaC25H25F3N4O6
Average Molecular Weight534.492
Monoisotopic Molecular Weight534.17261903
IUPAC Name1-[4-({2-methyl-6-nitro-2H,3H-imidazo[2,1-b][1,3]oxazol-2-yl}methoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidine
Traditional Name1-[4-({2-methyl-6-nitro-3H-imidazo[2,1-b][1,3]oxazol-2-yl}methoxy)phenyl]-4-[4-(trifluoromethoxy)phenoxy]piperidine
CAS Registry NumberNot Available
SMILES
CC1(COC2=CC=C(C=C2)N2CCC(CC2)OC2=CC=C(OC(F)(F)F)C=C2)CN2C=C(N=C2O1)[N+]([O-])=O
InChI Identifier
InChI=1S/C25H25F3N4O6/c1-24(15-31-14-22(32(33)34)29-23(31)38-24)16-35-18-4-2-17(3-5-18)30-12-10-20(11-13-30)36-19-6-8-21(9-7-19)37-25(26,27)28/h2-9,14,20H,10-13,15-16H2,1H3
InChI KeyXDAOLTSRNUSPPH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • Aminophenyl ether
  • Phenoxy compound
  • Nitroaromatic compound
  • Tertiary aliphatic/aromatic amine
  • Phenol ether
  • Dialkylarylamine
  • Aniline or substituted anilines
  • Nitroimidazole
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Imidolactam
  • N-substituted imidazole
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Trihalomethane
  • Tertiary amine
  • Organic nitro compound
  • C-nitro compound
  • Ether
  • Oxacycle
  • Azacycle
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organofluoride
  • Amine
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Halomethane
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic salt
  • Organic oxygen compound
  • Organic oxide
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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(5.71) g/LALOGPS
logP10(6.14) g/LChemAxon
logS10(-5.4) g/LALOGPS
pKa (Strongest Basic)5.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area101.12 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.85 m³·mol⁻¹ChemAxon
Polarizability51.86 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DelamanidCC1(COC2=CC=C(C=C2)N2CCC(CC2)OC2=CC=C(OC(F)(F)F)C=C2)CN2C=C(N=C2O1)[N+]([O-])=O4202.2Standard 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.
DelamanidCC1(COC2=CC=C(C=C2)N2CCC(CC2)OC2=CC=C(OC(F)(F)F)C=C2)CN2C=C(N=C2O1)[N+]([O-])=O3618.2Standard 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.
DelamanidCC1(COC2=CC=C(C=C2)N2CCC(CC2)OC2=CC=C(OC(F)(F)F)C=C2)CN2C=C(N=C2O1)[N+]([O-])=O3951.8Semi 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 ID9931606
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11756905
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 ]

Enzymes

General function:
Not Available
Specific function:
May function as a flavin mononucleotide (FMN)-dependent alkene reductase on substrates carrying alpha,beta-unsaturated carbonyl groups (ketones, aldehydes, carboxylic acids, esters, lactones or cyclic imides). The catalysis depends on NAD(P)H, which acts as hydride donor for the reduction. Seems to be involved in metabolic pathways required for efficient replication of amastigotes within macrophages.Acts as a FMN-dependent nitroreductase that activates anti-leishmanial bicyclic nitroaromatic prodrugs including delamanid, DNDI-VL-2098 and (R)-PA-824, forming toxic products that kill the parasites.
Gene Name:
(REFSEQ) PUTATIVE NADH:FLAVIN OXIDOREDUCTASE/NADH OXIDASE
Uniprot ID:
E9AGH7
Molecular weight:
39451.09