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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 02:03:34 UTC
Update Date2021-09-26 22:59:00 UTC
HMDB IDHMDB0248628
Secondary Accession NumbersNone
Metabolite Identification
Common NameArticaine
DescriptionN-[2-(methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidic acid, also known as carticaine, belongs to the class of organic compounds known as thiophene carboxylic acids and derivatives. Thiophene carboxylic acids and derivatives are compounds containing a thiophene ring which bears a carboxylic acid group (or a salt/ester thereof). Based on a literature review very few articles have been published on N-[2-(methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Articaine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Articaine 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
CarticaineKegg
N-[2-(Methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidateGenerator
CarticainMeSH
Carticaine hydrochlorideMeSH
Hoe 045MeSH
ArticainMeSH
Hoechst brand OF carticaine hydrochlorideMeSH
Hydrochloride, carticaineMeSH
UltracaineMeSH
Hoe-045MeSH
Chemical FormulaC13H20N2O3S
Average Molecular Weight284.374
Monoisotopic Molecular Weight284.119463206
IUPAC NameN-[2-(methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidic acid
Traditional Namecarticaine
CAS Registry NumberNot Available
SMILES
CCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC
InChI Identifier
InChI=1S/C13H20N2O3S/c1-5-6-14-9(3)12(16)15-10-8(2)7-19-11(10)13(17)18-4/h7,9,14H,5-6H2,1-4H3,(H,15,16)
InChI KeyQTGIAADRBBLJGA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiophene carboxylic acids and derivatives. Thiophene carboxylic acids and derivatives are compounds containing a thiophene ring which bears a carboxylic acid group (or a salt/ester thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiophenes
Sub ClassThiophene carboxylic acids and derivatives
Direct ParentThiophene carboxylic acids and derivatives
Alternative Parents
Substituents
  • Thiophene carboxylic acid or derivatives
  • Methyl ester
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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
logP1.9ALOGPS
logP0.96ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.42ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity77.53 m³·mol⁻¹ChemAxon
Polarizability30.8 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]+163.61930932474
DeepCCS[M-H]-161.26130932474
DeepCCS[M-2H]-194.14730932474
DeepCCS[M+Na]+169.71230932474
AllCCS[M+H]+165.332859911
AllCCS[M+H-H2O]+162.232859911
AllCCS[M+NH4]+168.232859911
AllCCS[M+Na]+169.032859911
AllCCS[M-H]-167.732859911
AllCCS[M+Na-2H]-168.332859911
AllCCS[M+HCOO]-169.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ArticaineCCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC2786.9Standard polar33892256
ArticaineCCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC2221.2Standard non polar33892256
ArticaineCCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC2144.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Articaine,2TMS,isomer #1CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C)[Si](C)(C)C2191.0Semi standard non polar33892256
Articaine,2TMS,isomer #1CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C)[Si](C)(C)C2166.1Standard non polar33892256
Articaine,2TMS,isomer #1CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C)[Si](C)(C)C2840.5Standard polar33892256
Articaine,2TBDMS,isomer #1CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2627.8Semi standard non polar33892256
Articaine,2TBDMS,isomer #1CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2503.3Standard non polar33892256
Articaine,2TBDMS,isomer #1CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2988.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Articaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g0-9710000000-17a712ab6964343fb8f42017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Articaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Articaine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Articaine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Articaine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Articaine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 10V, Positive-QTOFsplash10-000i-5190000000-2f877abe52116e1258b42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 20V, Positive-QTOFsplash10-000l-9000000000-0a18b19266dbc8f3bc9c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 40V, Positive-QTOFsplash10-0006-9100000000-91e2bdeec7aabd58a49d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 10V, Negative-QTOFsplash10-0f89-0190000000-8c22a5f16cbfcc830f1a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 20V, Negative-QTOFsplash10-0fl0-0590000000-3c5b853eac8c14c771b82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 40V, Negative-QTOFsplash10-0a6s-9720000000-ad595a95bd3d6a9368de2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 10V, Positive-QTOFsplash10-000i-0090000000-96d0ca67edf9c6365a452021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 20V, Positive-QTOFsplash10-059i-9440000000-17da9b566219ea11abbd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 40V, Positive-QTOFsplash10-0abc-9200000000-30cacb6ff9fab18becff2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 10V, Negative-QTOFsplash10-0udi-0190000000-ece2126e2377c42c05a82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 20V, Negative-QTOFsplash10-02ji-2940000000-aaa8465919bcdabc7df92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Articaine 40V, Negative-QTOFsplash10-000i-5900000000-e1c427cc8b6e8e4ae1fb2021-10-12Wishart 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 ID29837
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 ]