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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:24:04 UTC
Update Date2021-09-26 23:01:50 UTC
HMDB IDHMDB0250397
Secondary Accession NumbersNone
Metabolite Identification
Common NameCoelenterazine
DescriptionCoelenterazine belongs to the class of organic compounds known as imidazopyrazines. These are organic heteropolycyclic compounds containing a pyrazine ring fused to an imidazole ring. These also include hydrogenated derivatives of the imidazopyrazine moiety. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyrazine is a 6-membered ring consisting of six carbon atoms and two nitrogen centers at ring positions 1 and 4. Based on a literature review a significant number of articles have been published on Coelenterazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Coelenterazine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Coelenterazine 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
2-(4-Hydroxybenzyl)-6-(4-hydroxyphenyl)-8-benzyl-3,7-dihydroimidazo(1,2-a)pyrazin-3-oneHMDB
Chemical FormulaC26H21N3O3
Average Molecular Weight423.472
Monoisotopic Molecular Weight423.158291548
IUPAC Name8-benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]imidazo[1,2-a]pyrazin-3-ol
Traditional Name8-benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]imidazo[1,2-a]pyrazin-3-ol
CAS Registry NumberNot Available
SMILES
OC1=C(CC2=CC=C(O)C=C2)N=C2N1C=C(N=C2CC1=CC=CC=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C26H21N3O3/c30-20-10-6-18(7-11-20)15-23-26(32)29-16-24(19-8-12-21(31)13-9-19)27-22(25(29)28-23)14-17-4-2-1-3-5-17/h1-13,16,30-32H,14-15H2
InChI KeyLNCOEGVEEQDKGX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazopyrazines. These are organic heteropolycyclic compounds containing a pyrazine ring fused to an imidazole ring. These also include hydrogenated derivatives of the imidazopyrazine moiety. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyrazine is a 6-membered ring consisting of six carbon atoms and two nitrogen centers at ring positions 1 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrazines
Sub ClassNot Available
Direct ParentImidazopyrazines
Alternative Parents
Substituents
  • Imidazopyrazine
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • N-substituted imidazole
  • Pyrazine
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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
logP4.65ALOGPS
logP4.68ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)3.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.88 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.37 m³·mol⁻¹ChemAxon
Polarizability45.56 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+194.04130932474
DeepCCS[M-H]-191.64630932474
DeepCCS[M-2H]-224.59930932474
DeepCCS[M+Na]+199.95430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CoelenterazineOC1=C(CC2=CC=C(O)C=C2)N=C2N1C=C(N=C2CC1=CC=CC=C1)C1=CC=C(O)C=C15284.1Standard polar33892256
CoelenterazineOC1=C(CC2=CC=C(O)C=C2)N=C2N1C=C(N=C2CC1=CC=CC=C1)C1=CC=C(O)C=C13574.0Standard non polar33892256
CoelenterazineOC1=C(CC2=CC=C(O)C=C2)N=C2N1C=C(N=C2CC1=CC=CC=C1)C1=CC=C(O)C=C14479.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7659100000-4ae8ce909b08c4d088a12021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Coelenterazine GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coelenterazine 10V, Positive-QTOFsplash10-00di-0000900000-de35939946c9de0ba25c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coelenterazine 20V, Positive-QTOFsplash10-00di-0000900000-b4756be44962e9daa95a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coelenterazine 40V, Positive-QTOFsplash10-001i-2009100000-e24d37e5cd1f966a6cf22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coelenterazine 10V, Negative-QTOFsplash10-00di-0000900000-2bed83980643ccc5e9412021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coelenterazine 20V, Negative-QTOFsplash10-00di-0006900000-7a39d9aeecc0f8a29b0a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Coelenterazine 40V, Negative-QTOFsplash10-0006-9217000000-ac16fea97e28cd92efb42021-10-12Wishart LabView Spectrum
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 ID23166192
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoelenterazine
METLIN IDNot Available
PubChem Compound135445694
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 ]