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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:44 UTC
HMDB IDHMDB0014767
Secondary Accession Numbers
  • HMDB14767
Metabolite Identification
Common NameGuanabenz
DescriptionGuanabenz is only found in individuals that have used or taken this drug. It is an alpha-2 selective adrenergic agonist used as an antihypertensive agent. [PubChem]Guanabenz's antihypertensive effect is thought to be due to central alpha-adrenergic stimulation, which results in a decreased sympathetic outflow to the heart, kidneys, and peripheral vasculature in addition to a decreased systolic and diastolic blood pressure and a slight slowing of pulse rate. Chronic administration of guanabenz also causes a decrease in peripheral vascular resistance.
Structure
Data?1582753218
Synonyms
ValueSource
IcodextrinHMDB
ExtranealHMDB
IcodialHMDB
AdeptHMDB
Chemical FormulaC8H8Cl2N4
Average Molecular Weight231.082
Monoisotopic Molecular Weight230.01260169
IUPAC Name2-{[(2,6-dichlorophenyl)methylidene]amino}guanidine
Traditional Nameguanabenz
CAS Registry Number5051-62-7
SMILES
NC(N)=NN=CC1=C(Cl)C=CC=C1Cl
InChI Identifier
InChI=1S/C8H8Cl2N4/c9-6-2-1-3-7(10)5(6)4-13-14-8(11)12/h1-4H,(H4,11,12,14)
InChI KeyWDZVGELJXXEGPV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • 1,3-dichlorobenzene
  • Aryl halide
  • Aryl chloride
  • Guanidine
  • Carboximidamide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.089 g/LNot Available
LogP3.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.089 g/LALOGPS
logP2.25ALOGPS
logP1.71ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)6.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.15 m³·mol⁻¹ChemAxon
Polarizability21.58 ųChemAxon
Number of Rings1ChemAxon
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]+142.81330932474
DeepCCS[M-H]-140.44530932474
DeepCCS[M-2H]-175.61230932474
DeepCCS[M+Na]+150.50930932474
AllCCS[M+H]+145.832859911
AllCCS[M+H-H2O]+141.932859911
AllCCS[M+NH4]+149.332859911
AllCCS[M+Na]+150.432859911
AllCCS[M-H]-142.332859911
AllCCS[M+Na-2H]-142.932859911
AllCCS[M+HCOO]-143.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GuanabenzNC(N)=NN=CC1=C(Cl)C=CC=C1Cl2933.2Standard polar33892256
GuanabenzNC(N)=NN=CC1=C(Cl)C=CC=C1Cl1843.3Standard non polar33892256
GuanabenzNC(N)=NN=CC1=C(Cl)C=CC=C1Cl2298.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Guanabenz,1TMS,isomer #1C[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl2119.6Semi standard non polar33892256
Guanabenz,1TMS,isomer #1C[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl2090.9Standard non polar33892256
Guanabenz,1TMS,isomer #1C[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl3973.6Standard polar33892256
Guanabenz,2TMS,isomer #1C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C2219.6Semi standard non polar33892256
Guanabenz,2TMS,isomer #1C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C2089.6Standard non polar33892256
Guanabenz,2TMS,isomer #1C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C3913.1Standard polar33892256
Guanabenz,2TMS,isomer #2C[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C2133.0Semi standard non polar33892256
Guanabenz,2TMS,isomer #2C[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C2195.1Standard non polar33892256
Guanabenz,2TMS,isomer #2C[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C3922.0Standard polar33892256
Guanabenz,3TMS,isomer #1C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C2143.9Semi standard non polar33892256
Guanabenz,3TMS,isomer #1C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C2172.5Standard non polar33892256
Guanabenz,3TMS,isomer #1C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C3523.6Standard polar33892256
Guanabenz,4TMS,isomer #1C[Si](C)(C)N(C(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2171.8Semi standard non polar33892256
Guanabenz,4TMS,isomer #1C[Si](C)(C)N(C(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2364.5Standard non polar33892256
Guanabenz,4TMS,isomer #1C[Si](C)(C)N(C(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2826.1Standard polar33892256
Guanabenz,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl2319.7Semi standard non polar33892256
Guanabenz,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl2292.9Standard non polar33892256
Guanabenz,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl4073.6Standard polar33892256
Guanabenz,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C(C)(C)C2588.2Semi standard non polar33892256
Guanabenz,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C(C)(C)C2495.6Standard non polar33892256
Guanabenz,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C(C)(C)C3863.5Standard polar33892256
Guanabenz,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C2515.5Semi standard non polar33892256
Guanabenz,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C2627.9Standard non polar33892256
Guanabenz,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C3970.6Standard polar33892256
Guanabenz,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2707.6Semi standard non polar33892256
Guanabenz,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2827.8Standard non polar33892256
Guanabenz,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3556.1Standard polar33892256
Guanabenz,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2932.1Semi standard non polar33892256
Guanabenz,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3115.1Standard non polar33892256
Guanabenz,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3006.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Guanabenz GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9810000000-f0d376618ee2b864edf12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanabenz GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Guanabenz LC-ESI-qTof , Positive-QTOFsplash10-00di-2900000000-beb608df56c6a048bf6a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Guanabenz , positive-QTOFsplash10-00di-2900000000-beb608df56c6a048bf6a2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 10V, Positive-QTOFsplash10-0089-4490000000-2bae04fad880dd1834282016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 20V, Positive-QTOFsplash10-05a9-1920000000-9b3adfd03a13efbac3132016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 40V, Positive-QTOFsplash10-00di-6900000000-b522a66e030c19e643712016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 10V, Negative-QTOFsplash10-0570-2950000000-ac90bbc595f4bb6ee38a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 20V, Negative-QTOFsplash10-000i-2900000000-b85b83ffcfaeb978d0be2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 40V, Negative-QTOFsplash10-0006-9100000000-6b4179d611f85f624e3c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 10V, Positive-QTOFsplash10-001i-0090000000-e077511a1ba3c77b8e272021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 20V, Positive-QTOFsplash10-00ei-0940000000-dc63b8316484fdd291102021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 40V, Positive-QTOFsplash10-00di-2900000000-bd92a7171745f2a6e7632021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 10V, Negative-QTOFsplash10-004i-1290000000-0876824633774a9ca1672021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 20V, Negative-QTOFsplash10-004u-8970000000-a010839f293ddffed10e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanabenz 40V, Negative-QTOFsplash10-00lr-9400000000-8d4ab725b1000136caf92021-10-11Wishart 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 DB00629 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00629 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00629
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4642445
KEGG Compound IDC07034
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuanabenz
METLIN IDNot Available
PubChem Compound5702063
PDB IDNot Available
ChEBI ID101202
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 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. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
  2. Clement B, Demesmaeker M: Formation of guanoxabenz from guanabenz in human liver. A new metabolic marker for CYP1A2. Drug Metab Dispos. 1997 Nov;25(11):1266-71. [PubMed:9351903 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Piletz JE, Sletten K: Nonadrenergic imidazoline binding sites on human platelets. J Pharmacol Exp Ther. 1993 Dec;267(3):1493-502. [PubMed:8263811 ]
  2. Bockman CS, Jeffries WB, Abel PW: Binding and functional characterization of alpha-2 adrenergic receptor subtypes on pig vascular endothelium. J Pharmacol Exp Ther. 1993 Dec;267(3):1126-33. [PubMed:7903385 ]
  3. Bockman CS, Gonzalez-Cabrera I, Abel PW: Alpha-2 adrenoceptor subtype causing nitric oxide-mediated vascular relaxation in rats. J Pharmacol Exp Ther. 1996 Sep;278(3):1235-43. [PubMed:8819507 ]
  4. Galeotti N, Bartolini A, Ghelardini C: Alpha-2 agonist-induced memory impairment is mediated by the alpha-2A-adrenoceptor subtype. Behav Brain Res. 2004 Aug 31;153(2):409-17. [PubMed:15265636 ]
  5. van Zwieten PA: Centrally acting antihypertensives: a renaissance of interest. Mechanisms and haemodynamics. J Hypertens Suppl. 1997 Jan;15(1):S3-8. [PubMed:9050980 ]