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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 15:53:47 UTC
Update Date2021-09-26 23:11:09 UTC
HMDB IDHMDB0255910
Secondary Accession NumbersNone
Metabolite Identification
Common NameOctocrylene
DescriptionOctocrylene belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Based on a literature review a significant number of articles have been published on Octocrylene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Octocrylene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Octocrylene 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
OctocrileneKegg
2-Ethylhexyl 2-cyano-3,3-diphenyl-2-propenoateMeSH
2-Ethylhexyl 2-cyano-3,3-diphenylacrylateMeSH
2-Ethylhexyl 2-cyano-3,3-diphenylprop-2-enoic acidGenerator
Chemical FormulaC24H27NO2
Average Molecular Weight361.485
Monoisotopic Molecular Weight361.204179113
IUPAC Name2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate
Traditional Nameoctocrylene
CAS Registry NumberNot Available
SMILES
CCCCC(CC)COC(=O)C(C#N)=C(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3
InChI KeyFMJSMJQBSVNSBF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Fatty acid ester
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Nitrile
  • Carbonitrile
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP6.23ALOGPS
logP6.78ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area50.09 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity118.58 m³·mol⁻¹ChemAxon
Polarizability41.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+194.31530932474
DeepCCS[M-H]-191.29930932474
DeepCCS[M-2H]-226.8430932474
DeepCCS[M+Na]+203.1330932474
AllCCS[M+H]+190.732859911
AllCCS[M+H-H2O]+187.932859911
AllCCS[M+NH4]+193.232859911
AllCCS[M+Na]+193.932859911
AllCCS[M-H]-192.232859911
AllCCS[M+Na-2H]-192.632859911
AllCCS[M+HCOO]-193.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OctocryleneCCCCC(CC)COC(=O)C(C#N)=C(C1=CC=CC=C1)C1=CC=CC=C13403.2Standard polar33892256
OctocryleneCCCCC(CC)COC(=O)C(C#N)=C(C1=CC=CC=C1)C1=CC=CC=C12525.4Standard non polar33892256
OctocryleneCCCCC(CC)COC(=O)C(C#N)=C(C1=CC=CC=C1)C1=CC=CC=C12594.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Octocrylene GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-8392000000-7df1849d4d11f42cbe192021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octocrylene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Octocrylene 20V, Positive-QTOFsplash10-0f89-0090000000-9bc63b566bcc1ee3ee782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octocrylene 35V, Positive-QTOFsplash10-0ue9-0190000000-7bbeb1091ac567157bdd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octocrylene 10V, Positive-QTOFsplash10-0udi-0090000000-720e10b4cb30b5c5651a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octocrylene 20V, Positive-QTOFsplash10-0f89-0090000000-2ae1f0fc8653ed8a26bd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octocrylene 40V, Positive-QTOFsplash10-0f89-0190000000-c9c951db319416b853c22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octocrylene 30V, Positive-QTOFsplash10-001i-0090000000-a977ff239760b825aa772021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octocrylene 50V, Positive-QTOFsplash10-0ufr-0490000000-bdacf2f5dfcc29d4d8632021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octocrylene 10V, Positive-QTOFsplash10-03di-1937000000-e991ddf4a4f445b4a3582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octocrylene 20V, Positive-QTOFsplash10-03xr-4922000000-1d813a8f22fad6edc3a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octocrylene 40V, Positive-QTOFsplash10-014i-9620000000-bd6cd0d7223337914f862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octocrylene 10V, Negative-QTOFsplash10-03di-0759000000-57dbcea9ad84241544f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octocrylene 20V, Negative-QTOFsplash10-0f6x-0951000000-fcb8e4ebdf526eef37042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octocrylene 40V, Negative-QTOFsplash10-0v00-6690000000-47a9b34fd363cf122c332016-08-03Wishart 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 ID21165
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOctocrylene
METLIN IDNot Available
PubChem Compound22571
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1131441
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 ]