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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:21 UTC
HMDB IDHMDB0015302
Secondary Accession Numbers
  • HMDB15302
Metabolite Identification
Common NameMoclobemide
DescriptionMoclobemide is only found in individuals that have used or taken this drug. It is a reversible monoamine oxidase inhibitor (MAOI) selective for isoform A (RIMA) used to treat major depressive disorder.The mechanism of action of moclobemide involves the selective, reversible inhibition of MAO-A. This inhibition leads to a decrease in the metabolism and destruction of monoamines in the neurotransmitters. This results in an increase in the monoamines, relieving depressive symptoms.
Structure
Data?1582753281
Synonyms
ValueSource
MoclobemidaChEBI
MoclobemidumChEBI
AurorixKegg
4-Chlor-N-(2-morpholinoethyl)benzamidHMDB
4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamideHMDB
4-Chloro-N-(2-morpholin-4-yl-ethyl)-benzamideHMDB
MoclaimeHMDB
MoclamideHMDB
MoclamineHMDB
MoclobemidHMDB
p-Chloro-N-(2-morpholinoethyl)benzamideHMDB
1a Brand OF moclobemideHMDB
ArimaHMDB
Chem mart moclobemideHMDB
DBL MoclobemideHMDB
Faulding brand OF moclobemideHMDB
GenRX moclobemideHMDB
Hoffmann-la roche brand OF moclobemideHMDB
Kendrick brand OF moclobemideHMDB
ManerixHMDB
Moclobemid purenHMDB
Moclobemide alpharma brandHMDB
Moclobemide BC brandHMDB
Moclobemide bull brandHMDB
Moclobemide hexal brandHMDB
Moclobemide stadapharm brandHMDB
Moclobemide CT-arzneimittel brandHMDB
Moclobemide ratiopharm brandHMDB
NovoMoclobemideHMDB
Nu moclobemideHMDB
NuMoclobemideHMDB
Betapharm brand OF moclobemideHMDB
Ratiopharm brand OF moclobemideHMDB
Alphapharm brand OF moclobemideHMDB
Apo moclobemideHMDB
Apo-moclobemideHMDB
Azupharma brand OF moclobemideHMDB
Bull brand OF moclobemideHMDB
FerakenHMDB
MoclobamideHMDB
Moclobemid ratiopharmHMDB
Moclobemid-1a pharmaHMDB
Moclobemide healthsense brandHMDB
Moclobemide kendrick brandHMDB
Moclobemide novopharm brandHMDB
Moclobemide temmler brandHMDB
Moclobemide, genrxHMDB
MocloduraHMDB
MoclonormHMDB
Novo moclobemideHMDB
Novo-moclobemideHMDB
Novopharm brand OF moclobemideHMDB
Nu-moclobemideHMDB
Nu-pharm brand OF moclobemideHMDB
PMS-MoclobemideHMDB
Stadapharm brand OF moclobemideHMDB
Terry white chemists brand OF moclobemideHMDB
CT-Arzneimittel brand OF moclobemideHMDB
Esparma brand OF moclobemideHMDB
AZU, moclobemidHMDB
BC Brand OF moclobemideHMDB
DeprenormHMDB
Healthsense moclobemideHMDB
Hexal brand OF moclobemideHMDB
Hoffmann la roche brand OF moclobemideHMDB
MoclixHMDB
Moclobemid 1a pharmaHMDB
Moclobemid azuHMDB
Moclobemid stadaHMDB
Moclobemid-purenHMDB
Moclobemid-ratiopharmHMDB
Moclobemid1a pharmaHMDB
Moclobemide 1a brandHMDB
Moclobemide azupharma brandHMDB
Moclobemide faulding brandHMDB
Moclobemide nu-pharm brandHMDB
Moclobemide betapharm brandHMDB
Moclobemide esparma brandHMDB
Moclobemide, chem martHMDB
Moclobemide, healthsenseHMDB
Pharmascience brand OF moclobemideHMDB
Stada, moclobemidHMDB
Temmler brand OF moclobemideHMDB
Terry white chemists moclobemideHMDB
CT Arzneimittel brand OF moclobemideHMDB
Alpharma brand OF moclobemideHMDB
Apotex brand OF moclobemideHMDB
AurorexHMDB
Chem mart brand OF moclobemideHMDB
Healthsense brand OF moclobemideHMDB
Merck dura brand OF moclobemideHMDB
Moclobemid von CTHMDB
Moclobemide alphapharm brandHMDB
Moclobemide apotex brandHMDB
Moclobemide pharmascience brandHMDB
Moclobemide roche brandHMDB
Moclobemide, DBLHMDB
MoclobetaHMDB
Nu pharm brand OF moclobemideHMDB
PMS MoclobemideHMDB
RimocHMDB
Roche brand OF moclobemideHMDB
Von CT, moclobemidHMDB
Chemical FormulaC13H17ClN2O2
Average Molecular Weight268.739
Monoisotopic Molecular Weight268.097855505
IUPAC Name4-chloro-N-[2-(morpholin-4-yl)ethyl]benzamide
Traditional Namearima
CAS Registry Number71320-77-9
SMILES
ClC1=CC=C(C=C1)C(=O)NCCN1CCOCC1
InChI Identifier
InChI=1S/C13H17ClN2O2/c14-12-3-1-11(2-4-12)13(17)15-5-6-16-7-9-18-10-8-16/h1-4H,5-10H2,(H,15,17)
InChI KeyYHXISWVBGDMDLQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-halobenzoic acids and derivatives. These are benzoic acids or derivatives carrying a halogen atom at the 4-position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parent4-halobenzoic acids and derivatives
Alternative Parents
Substituents
  • 4-halobenzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Morpholine
  • Oxazinane
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility1.12 g/LNot Available
LogP1.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM162.530932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.12 g/LALOGPS
logP10(1.56) g/LALOGPS
logP10(1.45) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Acidic)14.73ChemAxon
pKa (Strongest Basic)6.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.93 m³·mol⁻¹ChemAxon
Polarizability28.28 ųChemAxon
Number of Rings2ChemAxon
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]+158.44330932474
DeepCCS[M-H]-156.05530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MoclobemideClC1=CC=C(C=C1)C(=O)NCCN1CCOCC13025.8Standard polar33892256
MoclobemideClC1=CC=C(C=C1)C(=O)NCCN1CCOCC12217.0Standard non polar33892256
MoclobemideClC1=CC=C(C=C1)C(=O)NCCN1CCOCC12256.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Moclobemide,1TMS,isomer #1C[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C12262.2Semi standard non polar33892256
Moclobemide,1TMS,isomer #1C[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C12216.0Standard non polar33892256
Moclobemide,1TMS,isomer #1C[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C13093.4Standard polar33892256
Moclobemide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C12506.9Semi standard non polar33892256
Moclobemide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C12427.0Standard non polar33892256
Moclobemide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C13172.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Moclobemide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmr-7930000000-f5021f0bbc3af0c7125e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moclobemide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-2900000000-c3230d468784464059912014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-3436435ae42cfbae36f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-ebaa843d45c4c64c1d3d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-00lr-0970000000-ab2fbe8b1feae9ff31412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-e3243f45e1029a4c0e712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-927950435244f3ac04e42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-6fe640038cbc911e2bae2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-26e37ce9ba0b814b74092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-07e0ca3dba489a2810ec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-00lr-0980000000-70103607e1e68c966be92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-ac7d3f04849dde0da3d22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001r-0900000000-6634fb6b07312ce02ee62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-c43f4a856e6d225766ef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-1231bd387729155af4ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-a885de4ee2be84e3748d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide , positive-QTOFsplash10-00lr-0950000000-2942178c0744617021812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide , positive-QTOFsplash10-0019-2900000000-bf1e7c693c96e9a699662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide 30V, Positive-QTOFsplash10-00lr-0980000000-8285f9b18fe84bc8a89e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide 75V, Positive-QTOFsplash10-000i-0900000000-c758091b215c9b205bf92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide 30V, Positive-QTOFsplash10-00lr-0970000000-774856bf69fc87f3c69d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 10V, Positive-QTOFsplash10-014i-0590000000-abe04a26339f19caa3d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 20V, Positive-QTOFsplash10-01q9-0910000000-f57d5ee7c11ceba003002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 40V, Positive-QTOFsplash10-08g3-9700000000-e573e8a9813088fd720e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 10V, Negative-QTOFsplash10-014i-0190000000-f48d994ed4df3ae5c60a2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 20V, Negative-QTOFsplash10-014i-3890000000-a3699392c661a9c95f772016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 40V, Negative-QTOFsplash10-03dl-9800000000-aaddfd0cc344b9fa04462016-08-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01171 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01171 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 IDDB01171
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4087
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMoclobemide
METLIN IDNot Available
PubChem Compound4235
PDB IDNot Available
ChEBI ID83531
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 oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
References
  1. Fisar Z, Hroudova J, Raboch J: Inhibition of monoamine oxidase activity by antidepressants and mood stabilizers. Neuro Endocrinol Lett. 2010;31(5):645-56. [PubMed:21200377 ]
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Berlin I, Zimmer R, Thiede HM, Payan C, Hergueta T, Robin L, Puech AJ: Comparison of the monoamine oxidase inhibiting properties of two reversible and selective monoamine oxidase-A inhibitors moclobemide and toloxatone, and assessment of their effect on psychometric performance in healthy subjects. Br J Clin Pharmacol. 1990 Dec;30(6):805-16. [PubMed:1705137 ]
  3. Fulton B, Benfield P: Moclobemide. An update of its pharmacological properties and therapeutic use. Drugs. 1996 Sep;52(3):450-74. [PubMed:8875133 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]