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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014627

Secondary Accession Numbers

HMDB14627

Metabolite Identification

Common Name

Brimonidine

Description

Brimonidine is only found in individuals that have used or taken this drug. It is a drug used to treat glaucoma. It acts via decreasing aqueous humor synthesis. [Wikipedia ]Brimonidine is an alpha adrenergic receptor agonist (primarily alpha-2). It has a peak ocular hypotensive effect occurring at two hours post-dosing. Fluorophotometric studies in animals and humans suggest that Brimonidine has a dual mechanism of action by reducing aqueous humor production and increasing uveoscleral outflow.

Structure

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

484
  Mrv0541 02231214432D          

 17 19  0  0  0  0            999 V2000
    5.0992   -1.2518    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.2020   -0.3499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -0.4268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694    0.8062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5511   -0.4554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5511    1.2518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2986   -0.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2986    0.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2  7  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 12  2  0  0  0  0
  5 16  1  0  0  0  0
  6 14  2  0  0  0  0
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
 10 11  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014627

> <DATABASE_NAME>
hmdb

> <SMILES>
BrC1=C(NC2=NCCN2)C=CC2=NC=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H10BrN5/c12-9-7(17-11-15-5-6-16-11)1-2-8-10(9)14-4-3-13-8/h1-4H,5-6H2,(H2,15,16,17)

> <INCHI_KEY>
XYLJNLCSTIOKRM-UHFFFAOYSA-N

> <FORMULA>
C11H10BrN5

> <MOLECULAR_WEIGHT>
292.135

> <EXACT_MASS>
291.011957992

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.74393406400084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
1.3715845303333332

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.31635216122091

> <JCHEM_POLAR_SURFACE_AREA>
62.2

> <JCHEM_REFRACTIVITY>
68.4944

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
brimonidine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 484                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Br   UNK     0       9.519  -2.337   0.000  0.00  0.00          Br+0
HETATM    2  N   UNK     0       4.110  -0.653   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       6.851  -0.797   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.356   1.505   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      12.229  -0.850   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      12.229   2.337   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.080   0.491   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850   1.825   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.517  -0.027   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.185  -0.027   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.519  -0.797   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.852  -0.027   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.185   1.513   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.852   1.513   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.519   2.283   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.624  -0.059   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.624   1.545   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    7    9                                                       
CONECT    3    9   10                                                       
CONECT    4    8    9                                                       
CONECT    5   12   16                                                       
CONECT    6   14   17                                                       
CONECT    7    2    8                                                       
CONECT    8    4    7                                                       
CONECT    9    2    3    4                                                  
CONECT   10    3   11   13                                                  
CONECT   11    1   10   12                                                  
CONECT   12    5   11   14                                                  
CONECT   13   10   15                                                       
CONECT   14    6   12   15                                                  
CONECT   15   13   14                                                       
CONECT   16    5   17                                                       
CONECT   17    6   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0014627
HETATM    1 BR1  UNL     1       1.519  -2.030   2.378  1.00  0.00          BR  
HETATM    2  C1  UNL     1       1.449  -0.800   0.925  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.219  -0.463   0.415  1.00  0.00           C  
HETATM    4  N1  UNL     1      -0.984  -1.006   0.942  1.00  0.00           N  
HETATM    5  C3  UNL     1      -2.266  -0.642   0.395  1.00  0.00           C  
HETATM    6  N2  UNL     1      -3.010  -1.332  -0.382  1.00  0.00           N  
HETATM    7  C4  UNL     1      -4.228  -0.663  -0.737  1.00  0.00           C  
HETATM    8  C5  UNL     1      -4.298   0.526   0.182  1.00  0.00           C  
HETATM    9  N3  UNL     1      -2.926   0.587   0.645  1.00  0.00           N  
HETATM   10  C6  UNL     1       0.201   0.441  -0.650  1.00  0.00           C  
HETATM   11  C7  UNL     1       1.386   0.949  -1.137  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.615   0.604  -0.617  1.00  0.00           C  
HETATM   13  N4  UNL     1       3.745   1.120  -1.119  1.00  0.00           N  
HETATM   14  C9  UNL     1       4.959   0.776  -0.602  1.00  0.00           C  
HETATM   15  C10 UNL     1       4.990  -0.115   0.448  1.00  0.00           C  
HETATM   16  N5  UNL     1       3.839  -0.626   0.943  1.00  0.00           N  
HETATM   17  C11 UNL     1       2.637  -0.294   0.440  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.904  -1.674   1.734  1.00  0.00           H  
HETATM   19  H2  UNL     1      -5.065  -1.374  -0.553  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.259  -0.361  -1.805  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.608   1.456  -0.340  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.985   0.297   1.012  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.508   1.417   1.091  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.749   0.724  -1.071  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.392   1.662  -1.975  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.876   1.195  -1.010  1.00  0.00           H  
HETATM   27  H10 UNL     1       5.961  -0.377   0.846  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   17
CONECT    3    4   10
CONECT    4    5   18
CONECT    5    6    6    9
CONECT    6    7
CONECT    7    8   19   20
CONECT    8    9   21   22
CONECT    9   23
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13   17
CONECT   13   14
CONECT   14   15   15   26
CONECT   15   16   27
CONECT   16   17   17
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline	ChEBI
Brimonidina	ChEBI
Brimonidinum	ChEBI
Bromoxidine	ChEBI
Brimonidine tartrate	HMDB
Alphagan	HMDB
Purite, brimonidine	HMDB
RatioBrimonidine	HMDB
Sanrosa	HMDB
Brimonidine tartrate (1:1)	HMDB
Brimonidine tartrate (1:1), (S-(r,r))-isomer	HMDB
5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline D-tartrate	HMDB
Ratio brimonidine	HMDB
Tartrate, brimonidine	HMDB
Mirvaso	HMDB
5-Bromo-6-(imidazolidinylideneamino)quinoxaline	HMDB
5-Bromo-6-(imidazolin-2-ylamino)quinoxaline	HMDB
Alphagan p	HMDB
Ratio-brimonidine	HMDB
Brimonidine purite	HMDB
Brimonidine tartrate, (R-(r,r))-isomer	HMDB

Chemical Formula

C₁₁H₁₀BrN₅

Average Molecular Weight

292.135

Monoisotopic Molecular Weight

291.011957992

IUPAC Name

5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)quinoxalin-6-amine

Traditional Name

brimonidine

CAS Registry Number

59803-98-4

SMILES

BrC1=C(NC2=NCCN2)C=CC2=NC=CN=C12

InChI Identifier

InChI=1S/C11H10BrN5/c12-9-7(17-11-15-5-6-16-11)1-2-8-10(9)14-4-3-13-8/h1-4H,5-6H2,(H2,15,16,17)

InChI Key

XYLJNLCSTIOKRM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinoxalines

Alternative Parents

Substituents

Quinoxaline
Aryl bromide
Aryl halide
Pyrazine
Benzenoid
2-imidazoline
Heteroaromatic compound
Guanidine
Azacycle
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organobromide
Organohalogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazoles (CHEBI:3175 )
quinoxaline derivative (CHEBI:3175 )
secondary amine (CHEBI:3175 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014627)

Process

Not Available

Role

Industrial application

Antihypertensive agent (HMDB: HMDB0014627)
Alpha-adrenergic agonist (HMDB: HMDB0014627)

Biological role

Adrenergic agonist (HMDB: HMDB0014627)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	207.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.15 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.37	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	8.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.2 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.49 m³·mol⁻¹	ChemAxon
Polarizability	25.74 Å³	ChemAxon
Number of Rings	3	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-2H]-	180.814	30932474
DeepCCS	[M+Na]+	155.664	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.4	32859911
AllCCS	[M+NH4]+	165.5	32859911
AllCCS	[M+Na]+	166.5	32859911
AllCCS	[M-H]-	156.8	32859911
AllCCS	[M+Na-2H]-	156.7	32859911
AllCCS	[M+HCOO]-	156.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.54 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6026 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.07 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	194.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	827.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	261.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	311.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	300.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	591.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	633.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	59.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	753.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	184.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	461.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	387.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	119.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Brimonidine	BrC1=C(NC2=NCCN2)C=CC2=NC=CN=C12	3158.3	Standard polar	33892256
Brimonidine	BrC1=C(NC2=NCCN2)C=CC2=NC=CN=C12	2551.9	Standard non polar	33892256
Brimonidine	BrC1=C(NC2=NCCN2)C=CC2=NC=CN=C12	2714.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Brimonidine,1TMS,isomer #1	C[Si](C)(C)N(C1=NCCN1)C1=CC=C2N=CC=NC2=C1Br	2658.4	Semi standard non polar	33892256
Brimonidine,1TMS,isomer #1	C[Si](C)(C)N(C1=NCCN1)C1=CC=C2N=CC=NC2=C1Br	2384.4	Standard non polar	33892256
Brimonidine,1TMS,isomer #1	C[Si](C)(C)N(C1=NCCN1)C1=CC=C2N=CC=NC2=C1Br	4793.3	Standard polar	33892256
Brimonidine,1TMS,isomer #2	C[Si](C)(C)N1CCN=C1NC1=CC=C2N=CC=NC2=C1Br	2751.0	Semi standard non polar	33892256
Brimonidine,1TMS,isomer #2	C[Si](C)(C)N1CCN=C1NC1=CC=C2N=CC=NC2=C1Br	2460.6	Standard non polar	33892256
Brimonidine,1TMS,isomer #2	C[Si](C)(C)N1CCN=C1NC1=CC=C2N=CC=NC2=C1Br	4236.8	Standard polar	33892256
Brimonidine,2TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=CC=C2N=CC=NC2=C1Br)[Si](C)(C)C	2602.7	Semi standard non polar	33892256
Brimonidine,2TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=CC=C2N=CC=NC2=C1Br)[Si](C)(C)C	2508.0	Standard non polar	33892256
Brimonidine,2TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=CC=C2N=CC=NC2=C1Br)[Si](C)(C)C	3864.0	Standard polar	33892256
Brimonidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=CC=C2N=CC=NC2=C1Br	2893.7	Semi standard non polar	33892256
Brimonidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=CC=C2N=CC=NC2=C1Br	2595.1	Standard non polar	33892256
Brimonidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=CC=C2N=CC=NC2=C1Br	4802.0	Standard polar	33892256
Brimonidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=CC=C2N=CC=NC2=C1Br	2993.6	Semi standard non polar	33892256
Brimonidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=CC=C2N=CC=NC2=C1Br	2659.2	Standard non polar	33892256
Brimonidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=CC=C2N=CC=NC2=C1Br	4369.9	Standard polar	33892256
Brimonidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=CC=C2N=CC=NC2=C1Br)[Si](C)(C)C(C)(C)C	2974.3	Semi standard non polar	33892256
Brimonidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=CC=C2N=CC=NC2=C1Br)[Si](C)(C)C(C)(C)C	2898.7	Standard non polar	33892256
Brimonidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=CC=C2N=CC=NC2=C1Br)[Si](C)(C)C(C)(C)C	3898.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Brimonidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-0190000000-cd1ec9d5bf9d24fab607	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brimonidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brimonidine 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 - Brimonidine , positive-QTOF	splash10-0006-0190000000-49c10e93a1977cbe01da	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 10V, Positive-QTOF	splash10-0006-0090000000-2f188927245c7fb3c618	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 20V, Positive-QTOF	splash10-0006-1090000000-fdfdc04ca6c5f2b62c3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 40V, Positive-QTOF	splash10-014i-9030000000-2d727aeec5962a767e61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 10V, Negative-QTOF	splash10-0006-0090000000-91069ec802c3a06026d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 20V, Negative-QTOF	splash10-0006-0090000000-7bd1085ed4367b683e29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 40V, Negative-QTOF	splash10-0002-2290000000-6351edb1d68a299dfd2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 10V, Positive-QTOF	splash10-0006-0090000000-5f6f82bdb9f8c51818c9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 20V, Positive-QTOF	splash10-0006-0090000000-5f6f82bdb9f8c51818c9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 40V, Positive-QTOF	splash10-000f-0490000000-2720653740ec8305f05d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 10V, Negative-QTOF	splash10-0006-0090000000-ffef408a4fb5db76cb85	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 20V, Negative-QTOF	splash10-0006-1090000000-0b1325c866472eaa216a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brimonidine 40V, Negative-QTOF	splash10-0f9j-3690000000-b5ba2dea82c37975ad75	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00484	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00484	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00484

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2341

KEGG Compound ID

C07886

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Brimonidine

METLIN ID

Not Available

PubChem Compound

2435

PDB ID

Not Available

ChEBI ID

3175

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

(). FDA label . .

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

References

Acheampong AA, Chien DS, Lam S, Vekich S, Breau A, Usansky J, Harcourt D, Munk SA, Nguyen H, Garst M, Tang-Liu D: Characterization of brimonidine metabolism with rat, rabbit, dog, monkey and human liver fractions and rabbit liver aldehyde oxidase. Xenobiotica. 1996 Oct;26(10):1035-55. [PubMed:8905918 ]

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

Rauly I, Ailhaud M, Wurch T, Pauwels PJ: alpha(2A)-adrenoceptor: G(alphai1) protein-mediated pertussis toxin-resistant attenuation of G(s) coupling to the cyclic AMP pathway. Biochem Pharmacol. 2000 Jun 15;59(12):1531-8. [PubMed:10799649 ]
Wikberg-Matsson A, Simonsen U: Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries. Invest Ophthalmol Vis Sci. 2001 Aug;42(9):2049-55. [PubMed:11481271 ]
Meana JJ, Barturen F, Garro MA, Garcia-Sevilla JA, Fontan A, Zarranz JJ: Decreased density of presynaptic alpha 2-adrenoceptors in postmortem brains of patients with Alzheimer's disease. J Neurochem. 1992 May;58(5):1896-904. [PubMed:1373179 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Alpha-2B 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 clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Trendelenburg AU, Philipp M, Meyer A, Klebroff W, Hein L, Starke K: All three alpha2-adrenoceptor types serve as autoreceptors in postganglionic sympathetic neurons. Naunyn Schmiedebergs Arch Pharmacol. 2003 Dec;368(6):504-12. Epub 2003 Nov 11. [PubMed:14610637 ]
Bohmann C, Schollmeyer P, Rump LC: Methoxamine inhibits noradrenaline release through activation of alpha 1- and alpha 2-adrenoceptors in rat isolated kidney: involvement of purines and prostaglandins. Naunyn Schmiedebergs Arch Pharmacol. 1993 Mar;347(3):273-9. [PubMed:8097565 ]

Enzyme Details

4. Alpha-2C 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
Gene Name:: ADRA2C
Uniprot ID:: P18825
Molecular weight:: 49521.6

References

Trendelenburg AU, Philipp M, Meyer A, Klebroff W, Hein L, Starke K: All three alpha2-adrenoceptor types serve as autoreceptors in postganglionic sympathetic neurons. Naunyn Schmiedebergs Arch Pharmacol. 2003 Dec;368(6):504-12. Epub 2003 Nov 11. [PubMed:14610637 ]
Orito K, Kishi M, Imaizumi T, Nakazawa T, Hashimoto A, Mori T, Kambe T: alpha(2)-adrenoceptor antagonist properties of OPC-28326, a novel selective peripheral vasodilator. Br J Pharmacol. 2001 Oct;134(4):763-70. [PubMed:11606316 ]
Zhang W, Ordway GA: The alpha2C-adrenoceptor modulates GABA release in mouse striatum. Brain Res Mol Brain Res. 2003 Apr 10;112(1-2):24-32. [PubMed:12670699 ]
Prinster SC, Holmqvist TG, Hall RA: Alpha2C-adrenergic receptors exhibit enhanced surface expression and signaling upon association with beta2-adrenergic receptors. J Pharmacol Exp Ther. 2006 Sep;318(3):974-81. Epub 2006 Jun 6. [PubMed:16757535 ]

Showing metabocard for Brimonidine (HMDB0014627)

MOL for HMDB0014627 (Brimonidine)

3D MOL for HMDB0014627 (Brimonidine)

3D SDF for HMDB0014627 (Brimonidine)

3D-SDF for HMDB0014627 (Brimonidine)

PDB for HMDB0014627 (Brimonidine)

3D PDB for HMDB0014627 (Brimonidine)

SMILES for HMDB0014627 (Brimonidine)

INCHI for HMDB0014627 (Brimonidine)

Structure for HMDB0014627 (Brimonidine)

3D Structure for HMDB0014627 (Brimonidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References