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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:48 UTC
HMDB IDHMDB0014945
Secondary Accession Numbers
  • HMDB14945
Metabolite Identification
Common NameProparacaine
DescriptionProparacaine is only found in individuals that have used or taken this drug. It is a topical anesthetic drug of the amino ester group. It is available as its hydrochloride salt in ophthalmic solutions at a concentration of 0.5%. [Wikipedia ]The exact mechanism whereby proparacaine and other local anesthetics influence the permeability of the cell membrane is unknown; however, several studies indicate that local anesthetics may limit sodium ion permeability through the lipid layer of the nerve cell membrane. Proparacaine may alter epithelial sodium channels through interaction with channel protein residues. This limitation prevents the fundamental change necessary for the generation of the action potential.
Structure
Data?1582753239
Synonyms
ValueSource
ProxymetacaineKegg
ProssimetacainaHMDB
ProximetacainumHMDB
OphtheticHMDB
ParcaineHMDB
AlcaineHMDB
Ocu-caineHMDB
Proxymetacaine hydrochlorideHMDB
AK-taineHMDB
KainairHMDB
ProxymethacaineHMDB
Chibro-kerakainHMDB
KéracaineHMDB
Minims proxymetacaine hydrochlorideHMDB
OphthaineHMDB
Proparakain-posHMDB
Proxymetacaine monohydrochlorideHMDB
Proparacaine hydrochlorideHMDB
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoateHMDB
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl esterHMDB
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate monohydrochlorideHMDB
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochloride*benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochlorideHMDB
Proparacaine HCLHMDB
Chemical FormulaC16H26N2O3
Average Molecular Weight294.3892
Monoisotopic Molecular Weight294.194342708
IUPAC Name2-(diethylamino)ethyl 3-amino-4-propoxybenzoate
Traditional Nameproparacaine
CAS Registry Number499-67-2
SMILES
CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC
InChI Identifier
InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3
InChI KeyKCLANYCVBBTKTO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Aminophenyl ether
  • Phenoxy compound
  • Benzoyl
  • Aniline or substituted anilines
  • Phenol ether
  • Alkyl aryl ether
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point182 - 183.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.39 g/LNot Available
LogP2.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.39 g/LALOGPS
logP2.97ALOGPS
logP2.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.79 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity86.04 m³·mol⁻¹ChemAxon
Polarizability34 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
DarkChem[M+H]+169.12431661259
DarkChem[M-H]-166.68831661259
DeepCCS[M+H]+173.99530932474
DeepCCS[M-H]-171.63730932474
DeepCCS[M-2H]-204.52230932474
DeepCCS[M+Na]+180.08830932474
AllCCS[M+H]+172.232859911
AllCCS[M+H-H2O]+169.232859911
AllCCS[M+NH4]+175.032859911
AllCCS[M+Na]+175.832859911
AllCCS[M-H]-173.732859911
AllCCS[M+Na-2H]-174.432859911
AllCCS[M+HCOO]-175.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ProparacaineCCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC3469.6Standard polar33892256
ProparacaineCCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC2366.1Standard non polar33892256
ProparacaineCCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC2370.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Proparacaine,1TMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C2491.7Semi standard non polar33892256
Proparacaine,1TMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C2428.6Standard non polar33892256
Proparacaine,1TMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C2996.0Standard polar33892256
Proparacaine,2TMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C)[Si](C)(C)C2428.0Semi standard non polar33892256
Proparacaine,2TMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C)[Si](C)(C)C2431.9Standard non polar33892256
Proparacaine,2TMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C)[Si](C)(C)C2766.3Standard polar33892256
Proparacaine,1TBDMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C(C)(C)C2670.1Semi standard non polar33892256
Proparacaine,1TBDMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C(C)(C)C2658.9Standard non polar33892256
Proparacaine,1TBDMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N[Si](C)(C)C(C)(C)C3073.1Standard polar33892256
Proparacaine,2TBDMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2818.0Semi standard non polar33892256
Proparacaine,2TBDMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2818.9Standard non polar33892256
Proparacaine,2TBDMS,isomer #1CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2951.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Proparacaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9320000000-1725fcdf405f1285cf5f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Proparacaine 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 - Proparacaine , positive-QTOFsplash10-0f6t-0590000000-0aae7080739b3c83b4a42017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 10V, Positive-QTOFsplash10-0f92-3790000000-19484885f2060a30ee392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 20V, Positive-QTOFsplash10-0udl-6940000000-b6eb0be7d6e42c79f6d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 40V, Positive-QTOFsplash10-0006-9300000000-8b40ab2bb2e6ca190ac62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 10V, Negative-QTOFsplash10-0006-2490000000-e0dd5d94666e639cd15f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 20V, Negative-QTOFsplash10-0udl-3890000000-83f45f2c670646cf13b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 40V, Negative-QTOFsplash10-0a4i-4910000000-080bada57e1dc3ab313c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 10V, Positive-QTOFsplash10-0udi-0940000000-dd6bde086183731626072021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 20V, Positive-QTOFsplash10-0udi-2950000000-6cf937b31cea35f9327a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 40V, Positive-QTOFsplash10-0udr-2900000000-74d2433c695036dfb8f52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 10V, Negative-QTOFsplash10-0006-0490000000-6934514b2f05a7f1e0432021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 20V, Negative-QTOFsplash10-0udj-2930000000-d9841e3d4745b761afc52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Proparacaine 40V, Negative-QTOFsplash10-0zg0-0900000000-acfb0c0e342bd2f577c82021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00807 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00807 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00807
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4766
KEGG Compound IDC07383
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProxymetacaine
METLIN IDNot Available
PubChem Compound4935
PDB IDNot Available
ChEBI ID309007
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 ReferencesNot Available

Enzymes

General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular weight:
220623.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Tella SR, Goldberg SR: Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12. [PubMed:9476974 ]