Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:43:13 UTC
Update Date2022-03-07 03:18:14 UTC
HMDB IDHMDB0240243
Secondary Accession NumbersNone
Metabolite Identification
Common NameHomochlorcyclizine
DescriptionHomochlorcyclizine, also known as curosajin or homoclomine, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. In humans, homochlorcyclizine is involved in the homochlorcyclizine h1-antihistamine action pathway. Homochlorcyclizine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Homochlorcyclizine.
Structure
Data?1563892735
Synonyms
ValueSource
CurosajinHMDB
(±)-homochlorcyclizineHMDB
HomochlorocyclizineHMDB
HomoclomineHMDB
HomodamonHMDB
HomorestarHMDB
LysilanHMDB
N-(p-Chlorobenzhydryl)-n'-methylhomopiperazineHMDB
NSC 25132HMDB
SA 97HMDB
SankuminHMDB
WicronHMDB
Homochlorcyclizine HCLHMDB
Homochlorocyclizine hydrochlorideHMDB
Homochlorocyclizine monohydrochlorideHMDB
1-((4-Chlorophenyl)phenylmethyl)hexahydro-4-methyl-1H-1,4-diazepineHMDB
HomochlorcyclizineHMDB, MeSH
Chemical FormulaC19H23ClN2
Average Molecular Weight314.86
Monoisotopic Molecular Weight314.1549764
IUPAC Name1-[(4-chlorophenyl)(phenyl)methyl]-4-methyl-1,4-diazepane
Traditional Namehomochlorcyclizine
CAS Registry Number848-53-3
SMILES
CN1CCCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C19H23ClN2/c1-21-12-5-13-22(15-14-21)19(16-6-3-2-4-7-16)17-8-10-18(20)11-9-17/h2-4,6-11,19H,5,12-15H2,1H3
InChI KeyWEUCDJCFJHYFRL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • 1,4-diazepane
  • Chlorobenzene
  • Diazepane
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
Process
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
logP4.53ALOGPS
logP4.21ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)8.63ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.6 m³·mol⁻¹ChemAxon
Polarizability35.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+174.23331661259
AllCCS[M-H]-180.15231661259
DeepCCS[M+H]+174.09930932474
DeepCCS[M-H]-171.74130932474
DeepCCS[M-2H]-204.62630932474
DeepCCS[M+Na]+180.19230932474
AllCCS[M+H]+174.232859911
AllCCS[M+H-H2O]+170.832859911
AllCCS[M+NH4]+177.432859911
AllCCS[M+Na]+178.332859911
AllCCS[M-H]-180.232859911
AllCCS[M+Na-2H]-179.932859911
AllCCS[M+HCOO]-179.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HomochlorcyclizineCN1CCCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C13259.6Standard polar33892256
HomochlorcyclizineCN1CCCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C12367.6Standard non polar33892256
HomochlorcyclizineCN1CCCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C12366.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Homochlorcyclizine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homochlorcyclizine 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 - Homochlorcyclizine 10V, Positive-QTOFsplash10-014i-0029000000-8a61986cf6d60bf81cda2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 20V, Positive-QTOFsplash10-0gb9-3096000000-959bed2bb20cae7061982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 40V, Positive-QTOFsplash10-0udl-9240000000-e1c510f4600b8a191aa92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 10V, Negative-QTOFsplash10-03di-0009000000-dc2748d860fa60954b1d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 20V, Negative-QTOFsplash10-03di-0159000000-65f5c34b0b35e0ac26b62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 40V, Negative-QTOFsplash10-02fx-5490000000-940d537678147878c1c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 10V, Positive-QTOFsplash10-014i-0039000000-e5538a12567efbc3dfa82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 20V, Positive-QTOFsplash10-0uxr-0094000000-a3c4471119f072f6e9622021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 40V, Positive-QTOFsplash10-0udi-1290000000-05fb262b2cc10b1e29162021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 10V, Negative-QTOFsplash10-03di-0009000000-c54768588510ddbc9bef2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 20V, Negative-QTOFsplash10-0ik9-0089000000-970bf509629d7033eebd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homochlorcyclizine 40V, Negative-QTOFsplash10-0ik9-1491000000-b2affbdb4464c5870a0d2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID3501
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHomochlorcyclizine
METLIN IDNot Available
PubChem Compound3627
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. Suzuki A, Yasui-Furukori N, Mihara K, Kondo T, Furukori H, Inoue Y, Kaneko S, Otani K: Histamine H1-receptor antagonists, promethazine and homochlorcyclizine, increase the steady-state plasma concentrations of haloperidol and reduced haloperidol. Ther Drug Monit. 2003 Apr;25(2):192-6. [PubMed:12657913 ]