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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 00:23:09 UTC
Update Date2021-09-26 22:57:02 UTC
HMDB IDHMDB0247379
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine
Description3-({3-methyl-1-[(3-methylbutyl)-C-hydroxycarbonimidoyl]butyl}-C-hydroxycarbonimidoyl)oxirane-2-carboxylic acid belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on 3-({3-methyl-1-[(3-methylbutyl)-C-hydroxycarbonimidoyl]butyl}-C-hydroxycarbonimidoyl)oxirane-2-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-(n-(3-carboxyoxirane-2-carbonyl)leucyl)isoamylamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine 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
3-({3-methyl-1-[(3-methylbutyl)-C-hydroxycarbonimidoyl]butyl}-C-hydroxycarbonimidoyl)oxirane-2-carboxylateGenerator
2,3-Epoxysuccinyl-L-leucylamido-3-methylbutaneMeSH
e 64-cMeSH
e 64CMeSH
e-64-cMeSH
e-64CMeSH
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine, monosodium saltMeSH
N-(N-(3-Transcarboxyoxirane-2-carbonyl)-L-leucyl)-3-methylbutylamineMeSH
N-(N-(L-3-trans-Carboxyoxirane -2-carbonyl)-L-leucyl)isoamylamineMeSH
Chemical FormulaC15H26N2O5
Average Molecular Weight314.382
Monoisotopic Molecular Weight314.184171945
IUPAC Name3-({3-methyl-1-[(3-methylbutyl)carbamoyl]butyl}carbamoyl)oxirane-2-carboxylic acid
Traditional Name3-({3-methyl-1-[(3-methylbutyl)carbamoyl]butyl}carbamoyl)oxirane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(C)CCNC(=O)C(CC(C)C)NC(=O)C1OC1C(O)=O
InChI Identifier
InChI=1S/C15H26N2O5/c1-8(2)5-6-16-13(18)10(7-9(3)4)17-14(19)11-12(22-11)15(20)21/h8-12H,5-7H2,1-4H3,(H,16,18)(H,17,19)(H,20,21)
InChI KeySCMSYZJDIQPSDI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentLeucine and derivatives
Alternative Parents
Substituents
  • Leucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Fatty amide
  • N-acyl-amine
  • Oxirane carboxylic acid
  • Fatty acyl
  • Oxirane carboxylic acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP1ALOGPS
logP1.08ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area108.03 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity78.82 m³·mol⁻¹ChemAxon
Polarizability33.82 ųChemAxon
Number of Rings1ChemAxon
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]+181.08230932474
DeepCCS[M-H]-178.72430932474
DeepCCS[M-2H]-211.6130932474
DeepCCS[M+Na]+187.17530932474
AllCCS[M+H]+175.932859911
AllCCS[M+H-H2O]+173.332859911
AllCCS[M+NH4]+178.432859911
AllCCS[M+Na]+179.132859911
AllCCS[M-H]-175.132859911
AllCCS[M+Na-2H]-175.832859911
AllCCS[M+HCOO]-176.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamineCC(C)CCNC(=O)C(CC(C)C)NC(=O)C1OC1C(O)=O3219.7Standard polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamineCC(C)CCNC(=O)C(CC(C)C)NC(=O)C1OC1C(O)=O2059.2Standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamineCC(C)CCNC(=O)C(CC(C)C)NC(=O)C1OC1C(O)=O2385.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)NC(=O)C1OC1C(=O)O[Si](C)(C)C)[Si](C)(C)C2343.4Semi standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)NC(=O)C1OC1C(=O)O[Si](C)(C)C)[Si](C)(C)C2320.6Standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)NC(=O)C1OC1C(=O)O[Si](C)(C)C)[Si](C)(C)C2866.6Standard polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TMS,isomer #2CC(C)CCNC(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C)[Si](C)(C)C2275.2Semi standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TMS,isomer #2CC(C)CCNC(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C)[Si](C)(C)C2306.9Standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TMS,isomer #2CC(C)CCNC(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C)[Si](C)(C)C2816.2Standard polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TMS,isomer #3CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O)[Si](C)(C)C)[Si](C)(C)C2332.2Semi standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TMS,isomer #3CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O)[Si](C)(C)C)[Si](C)(C)C2313.1Standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TMS,isomer #3CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O)[Si](C)(C)C)[Si](C)(C)C2954.9Standard polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,3TMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2301.8Semi standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,3TMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2407.5Standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,3TMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2583.8Standard polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TBDMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)NC(=O)C1OC1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2807.3Semi standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TBDMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)NC(=O)C1OC1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2674.6Standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TBDMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)NC(=O)C1OC1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3036.6Standard polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TBDMS,isomer #2CC(C)CCNC(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2764.2Semi standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TBDMS,isomer #2CC(C)CCNC(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2669.1Standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TBDMS,isomer #2CC(C)CCNC(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2992.9Standard polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TBDMS,isomer #3CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2824.2Semi standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TBDMS,isomer #3CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2674.0Standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,2TBDMS,isomer #3CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3104.5Standard polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,3TBDMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3011.9Semi standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,3TBDMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2944.8Standard non polar33892256
N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine,3TBDMS,isomer #1CC(C)CCN(C(=O)C(CC(C)C)N(C(=O)C1OC1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2924.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-6590000000-47512e5661b9946c69692021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine 10V, Positive-QTOFsplash10-014i-4049000000-c693bd68a4b802cb46532021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine 20V, Positive-QTOFsplash10-01w0-9421000000-0cf7bb618b22403891da2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine 40V, Positive-QTOFsplash10-00kf-9100000000-a3dec8ff67745908cffc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine 10V, Negative-QTOFsplash10-02ai-5936000000-56582e3dcfc992030e9e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine 20V, Negative-QTOFsplash10-001r-7900000000-4e382e5009911772fc872021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-(N-(3-Carboxyoxirane-2-carbonyl)leucyl)isoamylamine 40V, Negative-QTOFsplash10-0006-9200000000-af6940bf9b6c1d06d9912021-10-12Wishart 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 ID3076
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 ]