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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:20:33 UTC
HMDB IDHMDB0014616
Secondary Accession Numbers
  • HMDB14616
Metabolite Identification
Common NameHexylcaine
DescriptionHexylcaine, also known as cyclaine, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Hexylcaine is a drug which is used as a local anesthetic for surface application, infiltration or nerve block. Hexylcaine hydrochloride, also called cyclaine (Merck) or osmocaine, is a short-acting local anesthetic. Hexylcaine is a very strong basic compound (based on its pKa).
Structure
Data?1582753199
Synonyms
ValueSource
CyclaineHMDB
Hexylcaine hydrochlorideHMDB
Chemical FormulaC16H23NO2
Average Molecular Weight261.3593
Monoisotopic Molecular Weight261.172878985
IUPAC Name1-(cyclohexylamino)propan-2-yl benzoate
Traditional Namehexylcaine
CAS Registry Number532-77-4
SMILES
CC(CNC1CCCCC1)OC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3
InChI KeyDKLKMKYDWHYZTD-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
  • Benzoate ester
  • Benzoyl
  • Cyclohexylamine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0097 g/LNot Available
LogP3.9Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0097 g/LALOGPS
logP10(3.04) g/LALOGPS
logP10(3.83) g/LChemAxon
logS10(-4.4) g/LALOGPS
pKa (Strongest Basic)9.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity76.24 m³·mol⁻¹ChemAxon
Polarizability30.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+162.77631661259
DarkChem[M-H]-161.59831661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hexylcaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4910000000-9d078efa75ea2644f15d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexylcaine 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 - Hexylcaine 10V, Positive-QTOFsplash10-03dl-0960000000-666d132f25224cb4333c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 20V, Positive-QTOFsplash10-0006-5910000000-4a781f8df0db63e247e82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 40V, Positive-QTOFsplash10-0a59-9700000000-8f61edaf2f38ba400b932016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 10V, Negative-QTOFsplash10-03di-2980000000-176aaf9d71a17be5212a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 20V, Negative-QTOFsplash10-03fs-9770000000-50ea7352357a250316ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 40V, Negative-QTOFsplash10-05bb-9400000000-133ae6248b75f916d0842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 10V, Negative-QTOFsplash10-03di-0190000000-058708c045dbe4130aaa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 20V, Negative-QTOFsplash10-03mi-3950000000-192fa2b22b06abc093c12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 40V, Negative-QTOFsplash10-004i-9100000000-48021f84a4b8fbb807a52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 10V, Positive-QTOFsplash10-03dl-2980000000-0bf7df762ecb94eaee9f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 20V, Positive-QTOFsplash10-0a4i-9410000000-862fcbfa2afb557401392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexylcaine 40V, Positive-QTOFsplash10-0a4i-9420000000-f82fc7a14b4f6baa0c762021-09-24Wishart 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 DB00473 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00473 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00473
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10315
KEGG Compound IDC14172
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHexylcaine
METLIN IDNot Available
PubChem Compound10770
PDB IDNot Available
ChEBI ID309162
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 Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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 ]