Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015377
Secondary Accession Numbers
  • HMDB15377
Metabolite Identification
Common NameIsocarboxazid
DescriptionIsocarboxazid is only found in individuals that have used or taken this drug. It is an MAO inhibitor that is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in the treatment of panic disorder and the phobic disorders. (From AMA, Drug Evaluations Annual, 1994, p311). Isocarboxazid works by irreversibly blocking the action of a chemical substance known as monoamine oxidase (MAO) in the nervous system. MAO subtypes A and B are involved in the metabolism of serotonin and catecholamine neurotransmitters such as epinephrine, norepinephrine, and dopamine. Isocarboxazid, as a nonselective MAO inhibitor, binds irreversibly to monoamine oxidase–A (MAO-A) and monoamine oxidase–B (MAO-B). The reduced MAO activity results in an increased concentration of these neurotransmitters in storage sites throughout the central nervous system (CNS) and sympathetic nervous system. This increased availability of one or more monoamines is the basis for the antidepressant activity of MAO inhibitors.
Structure
Data?1582753290
Synonyms
ValueSource
MarplanKegg
IsocarbonazidHMDB
IsocarbossazideHMDB
IsocarboxazideHMDB
IsocarboxyzidHMDB
Chemical FormulaC12H13N3O2
Average Molecular Weight231.2505
Monoisotopic Molecular Weight231.100776675
IUPAC NameN'-benzyl-5-methyl-1,2-oxazole-3-carbohydrazide
Traditional Nameisocarboxazid
CAS Registry Number59-63-2
SMILES
CC1=CC(=NO1)C(=O)NNCC1=CC=CC=C1
InChI Identifier
InChI=1S/C12H13N3O2/c1-9-7-11(15-17-9)12(16)14-13-8-10-5-3-2-4-6-10/h2-7,13H,8H2,1H3,(H,14,16)
InChI KeyXKFPYPQQHFEXRZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Azole
  • Isoxazole
  • Heteroaromatic compound
  • Carboxylic acid hydrazide
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point105 - 106 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.22 g/LNot Available
LogP2.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM152.130932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP1.19ALOGPS
logP1.43ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.02ChemAxon
pKa (Strongest Basic)3.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.16 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.78 m³·mol⁻¹ChemAxon
Polarizability24.51 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
DarkChem[M+H]+153.98231661259
DarkChem[M-H]-155.38131661259
DeepCCS[M+H]+153.92630932474
DeepCCS[M-H]-151.56830932474
DeepCCS[M-2H]-184.64130932474
DeepCCS[M+Na]+160.01930932474
AllCCS[M+H]+153.232859911
AllCCS[M+H-H2O]+149.232859911
AllCCS[M+NH4]+157.032859911
AllCCS[M+Na]+158.132859911
AllCCS[M-H]-155.932859911
AllCCS[M+Na-2H]-155.932859911
AllCCS[M+HCOO]-156.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsocarboxazidCC1=CC(=NO1)C(=O)NNCC1=CC=CC=C12516.3Standard polar33892256
IsocarboxazidCC1=CC(=NO1)C(=O)NNCC1=CC=CC=C12066.3Standard non polar33892256
IsocarboxazidCC1=CC(=NO1)C(=O)NNCC1=CC=CC=C12066.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isocarboxazid,1TMS,isomer #1CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C)=NO12189.9Semi standard non polar33892256
Isocarboxazid,1TMS,isomer #1CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C)=NO12109.0Standard non polar33892256
Isocarboxazid,1TMS,isomer #1CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C)=NO12892.4Standard polar33892256
Isocarboxazid,1TMS,isomer #2CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C)=NO12133.1Semi standard non polar33892256
Isocarboxazid,1TMS,isomer #2CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C)=NO12061.4Standard non polar33892256
Isocarboxazid,1TMS,isomer #2CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C)=NO13052.7Standard polar33892256
Isocarboxazid,2TMS,isomer #1CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)=NO12169.5Semi standard non polar33892256
Isocarboxazid,2TMS,isomer #1CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)=NO12155.8Standard non polar33892256
Isocarboxazid,2TMS,isomer #1CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)=NO12688.3Standard polar33892256
Isocarboxazid,1TBDMS,isomer #1CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO12451.4Semi standard non polar33892256
Isocarboxazid,1TBDMS,isomer #1CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO12310.3Standard non polar33892256
Isocarboxazid,1TBDMS,isomer #1CC1=CC(C(=O)N(NCC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO12976.0Standard polar33892256
Isocarboxazid,1TBDMS,isomer #2CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO12386.7Semi standard non polar33892256
Isocarboxazid,1TBDMS,isomer #2CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO12261.5Standard non polar33892256
Isocarboxazid,1TBDMS,isomer #2CC1=CC(C(=O)NN(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)=NO13146.8Standard polar33892256
Isocarboxazid,2TBDMS,isomer #1CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NO12674.2Semi standard non polar33892256
Isocarboxazid,2TBDMS,isomer #1CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NO12518.1Standard non polar33892256
Isocarboxazid,2TBDMS,isomer #1CC1=CC(C(=O)N(N(CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NO12895.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isocarboxazid EI-B (Non-derivatized)splash10-0006-9600000000-952a7c1093fe532d1df32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isocarboxazid EI-B (Non-derivatized)splash10-0006-9600000000-952a7c1093fe532d1df32018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocarboxazid GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9510000000-c11f3aaa62df1be7ea3f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocarboxazid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocarboxazid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9500000000-6ab30f52fc69889b3fa22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocarboxazid LC-ESI-qTof , Positive-QTOFsplash10-0006-9210100010-78b2f412502a142509e62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isocarboxazid , positive-QTOFsplash10-0006-9210100010-78b2f412502a142509e62017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 10V, Positive-QTOFsplash10-001i-3290000000-9801781c24b97ecc08172016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 20V, Positive-QTOFsplash10-0006-9350000000-d8f9ca354f060f4330e22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 40V, Positive-QTOFsplash10-0006-9100000000-6cedb1354fdeece131f62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 10V, Negative-QTOFsplash10-001i-1690000000-07a8545573baa300826f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 20V, Negative-QTOFsplash10-001l-9640000000-077985063287a38f70952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 40V, Negative-QTOFsplash10-0kx0-9300000000-a6c0764f23b7adf2144e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 10V, Positive-QTOFsplash10-001l-6390000000-911dc29e6ed1ee4704332021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 20V, Positive-QTOFsplash10-0006-9100000000-4896c74c701f3ec4b2fd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 40V, Positive-QTOFsplash10-0006-9200000000-cc7b99641fc7414fb5592021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 10V, Negative-QTOFsplash10-001i-0090000000-b203703a00eee615a2072021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 20V, Negative-QTOFsplash10-001l-9110000000-fc267c475e490b4f9f3c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocarboxazid 40V, Negative-QTOFsplash10-000x-9100000000-b1b63bbca6e5cb19e8b82021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01247 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01247 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 IDDB01247
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3628
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsocarboxazid
METLIN IDNot Available
PubChem Compound3759
PDB IDNot Available
ChEBI ID775119
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. Kennedy SH, Piran N, Warsh JJ, Prendergast P, Mainprize E, Whynot C, Garfinkel PE: A trial of isocarboxazid in the treatment of bulimia nervosa. J Clin Psychopharmacol. 1988 Dec;8(6):391-6. [PubMed:3069879 ]

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. Mason ST: Chronic administration of type A monoamine oxidase inhibitors increases duration of thiopentone anaesthesia in the rat. Physiol Behav. 1985 Aug;35(2):201-3. [PubMed:4070383 ]
  2. Kettler R, Da Prada M, Burkard WP: Comparison of monoamine oxidase-A inhibition by moclobemide in vitro and ex vivo in rats. Acta Psychiatr Scand Suppl. 1990;360:101-2. [PubMed:2248058 ]
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. Thase ME, Trivedi MH, Rush AJ: MAOIs in the contemporary treatment of depression. Neuropsychopharmacology. 1995 May;12(3):185-219. [PubMed:7612154 ]
  3. Kettler R, Da Prada M, Burkard WP: Comparison of monoamine oxidase-A inhibition by moclobemide in vitro and ex vivo in rats. Acta Psychiatr Scand Suppl. 1990;360:101-2. [PubMed:2248058 ]