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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014767

Secondary Accession Numbers

HMDB14767

Metabolite Identification

Common Name

Guanabenz

Description

Guanabenz 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 629                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.415  -1.779   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       3.080  -1.779   0.000  0.00  0.00          Cl+0
HETATM    3  N   UNK     0       7.081   0.531   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.081   2.071   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       8.415   4.381   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.748   2.071   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.747  -1.779   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -2.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -2.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -4.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -4.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747  -4.859   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747  -0.239   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   2.841   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    4   13                                                       
CONECT    4    3   14                                                       
CONECT    5   14                                                            
CONECT    6   14                                                            
CONECT    7    8    9   13                                                  
CONECT    8    1    7   10                                                  
CONECT    9    2    7   11                                                  
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
CONECT   13    3    7                                                       
CONECT   14    4    5    6                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Icodextrin	HMDB
Extraneal	HMDB
Icodial	HMDB
Adept	HMDB

Chemical Formula

C₈H₈Cl₂N₄

Average Molecular Weight

231.082

Monoisotopic Molecular Weight

230.01260169

IUPAC Name

2-{[(2,6-dichlorophenyl)methylidene]amino}guanidine

Traditional Name

guanabenz

CAS Registry Number

5051-62-7

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 Key

WDZVGELJXXEGPV-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014767)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.089 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.089 g/L	ALOGPS
logP	2.25	ALOGPS
logP	1.71	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	6.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.15 m³·mol⁻¹	ChemAxon
Polarizability	21.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	142.813	30932474
DeepCCS	[M-H]-	140.445	30932474
DeepCCS	[M-2H]-	175.612	30932474
DeepCCS	[M+Na]+	150.509	30932474
AllCCS	[M+H]+	145.8	32859911
AllCCS	[M+H-H2O]+	141.9	32859911
AllCCS	[M+NH4]+	149.3	32859911
AllCCS	[M+Na]+	150.4	32859911
AllCCS	[M-H]-	142.3	32859911
AllCCS	[M+Na-2H]-	142.9	32859911
AllCCS	[M+HCOO]-	143.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Guanabenz	NC(N)=NN=CC1=C(Cl)C=CC=C1Cl	2933.2	Standard polar	33892256
Guanabenz	NC(N)=NN=CC1=C(Cl)C=CC=C1Cl	1843.3	Standard non polar	33892256
Guanabenz	NC(N)=NN=CC1=C(Cl)C=CC=C1Cl	2298.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Guanabenz,1TMS,isomer #1	C[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl	2119.6	Semi standard non polar	33892256
Guanabenz,1TMS,isomer #1	C[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl	2090.9	Standard non polar	33892256
Guanabenz,1TMS,isomer #1	C[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl	3973.6	Standard polar	33892256
Guanabenz,2TMS,isomer #1	C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C	2219.6	Semi standard non polar	33892256
Guanabenz,2TMS,isomer #1	C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C	2089.6	Standard non polar	33892256
Guanabenz,2TMS,isomer #1	C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C	3913.1	Standard polar	33892256
Guanabenz,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2133.0	Semi standard non polar	33892256
Guanabenz,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2195.1	Standard non polar	33892256
Guanabenz,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	3922.0	Standard polar	33892256
Guanabenz,3TMS,isomer #1	C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C	2143.9	Semi standard non polar	33892256
Guanabenz,3TMS,isomer #1	C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C	2172.5	Standard non polar	33892256
Guanabenz,3TMS,isomer #1	C[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C	3523.6	Standard polar	33892256
Guanabenz,4TMS,isomer #1	C[Si](C)(C)N(C(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2171.8	Semi standard non polar	33892256
Guanabenz,4TMS,isomer #1	C[Si](C)(C)N(C(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2364.5	Standard non polar	33892256
Guanabenz,4TMS,isomer #1	C[Si](C)(C)N(C(=NN=CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2826.1	Standard polar	33892256
Guanabenz,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl	2319.7	Semi standard non polar	33892256
Guanabenz,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl	2292.9	Standard non polar	33892256
Guanabenz,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NN=CC1=C(Cl)C=CC=C1Cl	4073.6	Standard polar	33892256
Guanabenz,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C(C)(C)C	2588.2	Semi standard non polar	33892256
Guanabenz,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C(C)(C)C	2495.6	Standard non polar	33892256
Guanabenz,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NN=CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C(C)(C)C	3863.5	Standard polar	33892256
Guanabenz,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2515.5	Semi standard non polar	33892256
Guanabenz,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2627.9	Standard non polar	33892256
Guanabenz,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NN=CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	3970.6	Standard polar	33892256
Guanabenz,3TBDMS,isomer #1	CC(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)C	2707.6	Semi standard non polar	33892256
Guanabenz,3TBDMS,isomer #1	CC(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)C	2827.8	Standard non polar	33892256
Guanabenz,3TBDMS,isomer #1	CC(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)C	3556.1	Standard polar	33892256
Guanabenz,4TBDMS,isomer #1	CC(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)C	2932.1	Semi standard non polar	33892256
Guanabenz,4TBDMS,isomer #1	CC(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)C	3115.1	Standard non polar	33892256
Guanabenz,4TBDMS,isomer #1	CC(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)C	3006.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Guanabenz GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9810000000-f0d376618ee2b864edf1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guanabenz GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guanabenz LC-ESI-qTof , Positive-QTOF	splash10-00di-2900000000-beb608df56c6a048bf6a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guanabenz , positive-QTOF	splash10-00di-2900000000-beb608df56c6a048bf6a	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 10V, Positive-QTOF	splash10-0089-4490000000-2bae04fad880dd183428	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 20V, Positive-QTOF	splash10-05a9-1920000000-9b3adfd03a13efbac313	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 40V, Positive-QTOF	splash10-00di-6900000000-b522a66e030c19e64371	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 10V, Negative-QTOF	splash10-0570-2950000000-ac90bbc595f4bb6ee38a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 20V, Negative-QTOF	splash10-000i-2900000000-b85b83ffcfaeb978d0be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 40V, Negative-QTOF	splash10-0006-9100000000-6b4179d611f85f624e3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 10V, Positive-QTOF	splash10-001i-0090000000-e077511a1ba3c77b8e27	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 20V, Positive-QTOF	splash10-00ei-0940000000-dc63b8316484fdd29110	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 40V, Positive-QTOF	splash10-00di-2900000000-bd92a7171745f2a6e763	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 10V, Negative-QTOF	splash10-004i-1290000000-0876824633774a9ca167	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 20V, Negative-QTOF	splash10-004u-8970000000-a010839f293ddffed10e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanabenz 40V, Negative-QTOF	splash10-00lr-9400000000-8d4ab725b1000136caf9	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00629	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00629	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00629

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4642445

KEGG Compound ID

C07034

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Guanabenz

METLIN ID

Not Available

PubChem Compound

5702063

PDB ID

Not Available

ChEBI ID

101202

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 1A2

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

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 ]
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 ]

Enzyme Details

2. Alpha-2A adrenergic receptor

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

Piletz JE, Sletten K: Nonadrenergic imidazoline binding sites on human platelets. J Pharmacol Exp Ther. 1993 Dec;267(3):1493-502. [PubMed:8263811 ]
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 ]
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 ]
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 ]
van Zwieten PA: Centrally acting antihypertensives: a renaissance of interest. Mechanisms and haemodynamics. J Hypertens Suppl. 1997 Jan;15(1):S3-8. [PubMed:9050980 ]

Showing metabocard for Guanabenz (HMDB0014767)

MOL for HMDB0014767 (Guanabenz)

3D MOL for HMDB0014767 (Guanabenz)

3D SDF for HMDB0014767 (Guanabenz)

3D-SDF for HMDB0014767 (Guanabenz)

PDB for HMDB0014767 (Guanabenz)

3D PDB for HMDB0014767 (Guanabenz)

SMILES for HMDB0014767 (Guanabenz)

INCHI for HMDB0014767 (Guanabenz)

Structure for HMDB0014767 (Guanabenz)

3D Structure for HMDB0014767 (Guanabenz)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References