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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:22:43 UTC
Update Date2022-03-07 02:56:44 UTC
HMDB IDHMDB0040793
Secondary Accession Numbers
  • HMDB40793
Metabolite Identification
Common NameAcidissiminol epoxide
DescriptionAcidissiminol epoxide belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. Acidissiminol epoxide has been detected, but not quantified in, beverages and fruits. This could make acidissiminol epoxide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Acidissiminol epoxide.
Structure
Data?1563863588
Synonyms
ValueSource
SeverineHMDB
Severin protein, dictyosteliumMeSH, HMDB
N-[2-(4-{[(2E)-5-(3,3-dimethyloxiran-2-yl)-4-hydroxy-3-methylpent-2-en-1-yl]oxy}phenyl)ethyl]benzenecarboximidateGenerator
SeverinMeSH
Chemical FormulaC25H31NO4
Average Molecular Weight409.5179
Monoisotopic Molecular Weight409.225308485
IUPAC NameN-[2-(4-{[(2E)-5-(3,3-dimethyloxiran-2-yl)-4-hydroxy-3-methylpent-2-en-1-yl]oxy}phenyl)ethyl]benzamide
Traditional NameN-[2-(4-{[(2E)-5-(3,3-dimethyloxiran-2-yl)-4-hydroxy-3-methylpent-2-en-1-yl]oxy}phenyl)ethyl]benzamide
CAS Registry Number139165-01-8
SMILES
C\C(=C/COC1=CC=C(CCNC(=O)C2=CC=CC=C2)C=C1)C(O)CC1OC1(C)C
InChI Identifier
InChI=1S/C25H31NO4/c1-18(22(27)17-23-25(2,3)30-23)14-16-29-21-11-9-19(10-12-21)13-15-26-24(28)20-7-5-4-6-8-20/h4-12,14,22-23,27H,13,15-17H2,1-3H3,(H,26,28)/b18-14+
InChI KeyQQKKFVXSQXUHPI-NBVRZTHBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzamides
Alternative Parents
Substituents
  • Benzamide
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Alkyl aryl ether
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point146 - 149 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP3.74ALOGPS
logP3.64ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)14.4ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area71.09 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity119.09 m³·mol⁻¹ChemAxon
Polarizability47.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.51931661259
DarkChem[M-H]-192.95731661259
DeepCCS[M+H]+200.17430932474
DeepCCS[M-H]-197.81630932474
DeepCCS[M-2H]-231.70430932474
DeepCCS[M+Na]+206.93330932474
AllCCS[M+H]+205.532859911
AllCCS[M+H-H2O]+203.132859911
AllCCS[M+NH4]+207.732859911
AllCCS[M+Na]+208.332859911
AllCCS[M-H]-201.632859911
AllCCS[M+Na-2H]-202.332859911
AllCCS[M+HCOO]-203.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acidissiminol epoxideC\C(=C/COC1=CC=C(CCNC(=O)C2=CC=CC=C2)C=C1)C(O)CC1OC1(C)C4203.9Standard polar33892256
Acidissiminol epoxideC\C(=C/COC1=CC=C(CCNC(=O)C2=CC=CC=C2)C=C1)C(O)CC1OC1(C)C3295.6Standard non polar33892256
Acidissiminol epoxideC\C(=C/COC1=CC=C(CCNC(=O)C2=CC=CC=C2)C=C1)C(O)CC1OC1(C)C3526.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acidissiminol epoxide,1TMS,isomer #1C/C(=C\COC1=CC=C(CCNC(=O)C2=CC=CC=C2)C=C1)C(CC1OC1(C)C)O[Si](C)(C)C3404.7Semi standard non polar33892256
Acidissiminol epoxide,1TMS,isomer #2C/C(=C\COC1=CC=C(CCN(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1)C(O)CC1OC1(C)C3302.0Semi standard non polar33892256
Acidissiminol epoxide,2TMS,isomer #1C/C(=C\COC1=CC=C(CCN(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1)C(CC1OC1(C)C)O[Si](C)(C)C3231.6Semi standard non polar33892256
Acidissiminol epoxide,2TMS,isomer #1C/C(=C\COC1=CC=C(CCN(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1)C(CC1OC1(C)C)O[Si](C)(C)C3047.9Standard non polar33892256
Acidissiminol epoxide,1TBDMS,isomer #1C/C(=C\COC1=CC=C(CCNC(=O)C2=CC=CC=C2)C=C1)C(CC1OC1(C)C)O[Si](C)(C)C(C)(C)C3640.6Semi standard non polar33892256
Acidissiminol epoxide,1TBDMS,isomer #2C/C(=C\COC1=CC=C(CCN(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1)C(O)CC1OC1(C)C3572.4Semi standard non polar33892256
Acidissiminol epoxide,2TBDMS,isomer #1C/C(=C\COC1=CC=C(CCN(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1)C(CC1OC1(C)C)O[Si](C)(C)C(C)(C)C3697.5Semi standard non polar33892256
Acidissiminol epoxide,2TBDMS,isomer #1C/C(=C\COC1=CC=C(CCN(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1)C(CC1OC1(C)C)O[Si](C)(C)C(C)(C)C3433.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acidissiminol epoxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-4935000000-3c3bd356922ad5ed1daa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acidissiminol epoxide GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-5932200000-d033a82e42abb50aae8a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acidissiminol epoxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 10V, Positive-QTOFsplash10-06xx-1839400000-7e707efdcf038a3ce9972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 20V, Positive-QTOFsplash10-0a4i-4944000000-bf92fc041ea400fa3d532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 40V, Positive-QTOFsplash10-0a4i-9820000000-7a0a331312bf3f56b1dc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 10V, Negative-QTOFsplash10-0a4l-4142900000-de3394d9ddebd72065eb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 20V, Negative-QTOFsplash10-006x-8692100000-e80cf0febd6c89e80b682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 40V, Negative-QTOFsplash10-00fu-9820000000-4e626af31c25f7ceebd82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 10V, Positive-QTOFsplash10-03kl-1449500000-ed1486e709bd707e61aa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 20V, Positive-QTOFsplash10-00di-1019000000-582e01cc726c5270463a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 40V, Positive-QTOFsplash10-056r-4911000000-1a390ef5aea35f97b9f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 10V, Negative-QTOFsplash10-0a4i-0020900000-927af643c699fa9499782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 20V, Negative-QTOFsplash10-0a4l-8435900000-ed36bf3c357a94855c612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acidissiminol epoxide 40V, Negative-QTOFsplash10-002f-9440200000-c1e97e5c9c9a675fb47b2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB020609
KNApSAcK IDC00054390
Chemspider ID4515560
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5363185
PDB IDNot Available
ChEBI ID175287
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1886441
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .