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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:49 UTC
HMDB IDHMDB0015006
Secondary Accession Numbers
  • HMDB15006
Metabolite Identification
Common NameBenzonatate
DescriptionBenzonatate is a non-narcotic oral antitussive (cough suppressant) drug which works by anesthetizing the tissues of the lungs and pleura responsible for the cough reflex. It is chemically related to other ester anesthetics such as procaine. It has an anesthetic (numbing) action similar to that of benzocaine and 'numbs' the stretch sensors in the lungs. It is the stretching of these sensors with breathing that causes the cough. It was approved by the FDA in 1958.
Structure
Data?1582753247
Synonyms
ValueSource
2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-yl p-(butylamino)benzoateChEBI
2-[2-[2-[2-[2-[2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoateChEBI
3,6,9,12,15,18,21,24,27-Nonaoxaoctacosyl 4-butylaminobenzoateChEBI
4-(Butylamino)benzoic acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl esterChEBI
BenzonatatoChEBI
BenzonatatumChEBI
BenzononatineChEBI
Nonaethyleneglycol monomethyl ether p-N-butylaminobenzoateChEBI
p-Butylaminobenzoic acid omega-O-methylnonaethyleneglycol esterChEBI
Tessalon perlesKegg
2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-yl p-(butylamino)benzoic acidGenerator
2-[2-[2-[2-[2-[2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoic acidGenerator
3,6,9,12,15,18,21,24,27-Nonaoxaoctacosyl 4-butylaminobenzoic acidGenerator
4-(Butylamino)benzoate 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl esterGenerator
Nonaethyleneglycol monomethyl ether p-N-butylaminobenzoic acidGenerator
p-Butylaminobenzoate omega-O-methylnonaethyleneglycol esterGenerator
Benzonatic acidGenerator
TessalonHMDB
Chemical FormulaC30H53NO11
Average Molecular Weight603.7419
Monoisotopic Molecular Weight603.361861543
IUPAC Name2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
Traditional Namebenzonatate
CAS Registry Number104-31-4
SMILES
CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC
InChI Identifier
InChI=1S/C30H53NO11/c1-3-4-9-31-29-7-5-28(6-8-29)30(32)42-27-26-41-25-24-40-23-22-39-21-20-38-19-18-37-17-16-36-15-14-35-13-12-34-11-10-33-2/h5-8,31H,3-4,9-27H2,1-2H3
InChI KeyMAFMQEKGGFWBAB-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
  • Benzoyl
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Secondary aliphatic/aromatic amine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Secondary amine
  • Dialkyl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0016 g/LNot Available
LogP1.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP2.09ALOGPS
logP2.35ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)3.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area121.4 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity161.54 m³·mol⁻¹ChemAxon
Polarizability67.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+242.93831661259
DarkChem[M-H]-234.02131661259
DeepCCS[M+H]+229.97130932474
DeepCCS[M-H]-227.21630932474
DeepCCS[M-2H]-261.90530932474
DeepCCS[M+Na]+237.13330932474
AllCCS[M+H]+233.032859911
AllCCS[M+H-H2O]+232.432859911
AllCCS[M+NH4]+233.532859911
AllCCS[M+Na]+233.632859911
AllCCS[M-H]-230.332859911
AllCCS[M+Na-2H]-234.632859911
AllCCS[M+HCOO]-239.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzonatateCCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC5202.5Standard polar33892256
BenzonatateCCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC4175.1Standard non polar33892256
BenzonatateCCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC4420.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzonatate,1TMS,isomer #1CCCCN(C1=CC=C(C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)C=C1)[Si](C)(C)C4386.4Semi standard non polar33892256
Benzonatate,1TMS,isomer #1CCCCN(C1=CC=C(C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)C=C1)[Si](C)(C)C4027.5Standard non polar33892256
Benzonatate,1TMS,isomer #1CCCCN(C1=CC=C(C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)C=C1)[Si](C)(C)C5238.9Standard polar33892256
Benzonatate,1TBDMS,isomer #1CCCCN(C1=CC=C(C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)C=C1)[Si](C)(C)C(C)(C)C4561.1Semi standard non polar33892256
Benzonatate,1TBDMS,isomer #1CCCCN(C1=CC=C(C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)C=C1)[Si](C)(C)C(C)(C)C4075.3Standard non polar33892256
Benzonatate,1TBDMS,isomer #1CCCCN(C1=CC=C(C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)C=C1)[Si](C)(C)C(C)(C)C5242.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzonatate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ba-4789430000-3e3f5cdbfca7adf273242017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzonatate LC-ESI-qTof , Positive-QTOFsplash10-0nmm-2794000000-e2d12296cd52bc5b6c1b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzonatate , positive-QTOFsplash10-004i-2900000000-3718c62c83080a92ccdd2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 10V, Positive-QTOFsplash10-0w4i-3922626000-5dc7fe4297607d083b742016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 20V, Positive-QTOFsplash10-0a4i-9744340000-9f08af439f9cd35146712016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 40V, Positive-QTOFsplash10-0a4i-9665010000-1bf3fbd87ab1a87e011c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 10V, Negative-QTOFsplash10-0f6x-0922113000-2d47eaeef804822700922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 20V, Negative-QTOFsplash10-0597-2921111000-2cc95d4ee244c90547382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 40V, Negative-QTOFsplash10-0006-4920000000-1c2d9b1acf4ebda284382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 10V, Positive-QTOFsplash10-0ab9-9321011000-f4806fb7494d3b14849c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 20V, Positive-QTOFsplash10-0a4i-9200010000-4fd975b439aea833149f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 40V, Positive-QTOFsplash10-0a4i-9600000000-ebbc2bf3aeb5569f49242021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 10V, Negative-QTOFsplash10-0a6r-9731100000-3824f37521f4fc6505b82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 20V, Negative-QTOFsplash10-0btc-9411100000-2057400c582684721e812021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzonatate 40V, Negative-QTOFsplash10-000l-4910000000-a4a3ebc1f733a1ccfe9d2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00868 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00868 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00868
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7413
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzonatate
METLIN IDNot Available
PubChem Compound7699
PDB IDNot Available
ChEBI ID3032
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. Cohen V, Jellinek SP, Stansfield L, Truong H, Baseluos C, Marshall JP: Cardiac arrest with residual blindness after overdose of Tessalon(R) (benzonatate) perles. J Emerg Med. 2011 Aug;41(2):166-71. doi: 10.1016/j.jemermed.2009.08.027. Epub 2009 Nov 5. [PubMed:19892505 ]

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 ]