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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015153

Secondary Accession Numbers

HMDB15153

Metabolite Identification

Common Name

Guanfacine

Description

Guanfacine, also known as estulic or SPD 503, belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. In 1986, guanfacine was approved by the FDA for the treatment of hypertension under the brand name Tenex (Drugs@FDA). It is available as a generic medication. Guanfacine is a very strong basic compound (based on its pKa). Other side effect may include anxiety, low blood pressure, depression, and urinary problems.

Structure

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

 
  Mrv0541 02231215112D          
 
 15 15  0  0  0  0            999 V2000
   14.9998   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2821   -9.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9929  -10.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7106   -9.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5713   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7106  -10.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2787  -10.7407    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.4248   -9.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7071   -8.2649    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.8571   -9.0959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5713  -10.3355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4248  -10.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1393   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4251   -9.0959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1393  -10.3355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  8 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015153

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C9H9Cl2N3O/c10-6-2-1-3-7(11)5(6)4-8(15)14-9(12)13/h1-3H,4H2,(H4,12,13,14,15)

> <INCHI_KEY>
INJOMKTZOLKMBF-UHFFFAOYSA-N

> <FORMULA>
C9H9Cl2N3O

> <MOLECULAR_WEIGHT>
246.093

> <EXACT_MASS>
245.012267339

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.74756627970052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-carbamimidoyl-2-(2,6-dichlorophenyl)acetamide

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
1.7370317963333333

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.937505810438758

> <JCHEM_PKA_STRONGEST_BASIC>
6.647665414541562

> <JCHEM_POLAR_SURFACE_AREA>
78.97

> <JCHEM_REFRACTIVITY>
69.63409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
guanfacine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      28.000 -17.754   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.660 -16.979   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.987 -19.287   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.326 -16.973   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.333 -17.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.326 -20.056   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      26.654 -20.049   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      30.660 -17.742   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      29.320 -15.428   0.000  0.00  0.00          Cl+0
HETATM   10  N   UNK     0      24.000 -16.979   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      25.333 -19.293   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      30.660 -19.287   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.660 -17.754   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      21.327 -16.979   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      22.660 -19.293   0.000  0.00  0.00           N+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    3   12                                                       
CONECT    7    3                                                            
CONECT    8    4   12                                                       
CONECT    9    4                                                            
CONECT   10    5   13                                                       
CONECT   11    5                                                            
CONECT   12    6    8                                                       
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Estulic	Kegg
SPD 503	HMDB
Monohydrochloride, guanfacine	HMDB
Guanfacine monohydrochloride	HMDB
Tenex	HMDB
Hydrochloride, guanfacine	HMDB
Guanfacine hydrochloride	HMDB

Chemical Formula

C₉H₉Cl₂N₃O

Average Molecular Weight

246.093

Monoisotopic Molecular Weight

245.012267339

IUPAC Name

N-carbamimidoyl-2-(2,6-dichlorophenyl)acetamide

Traditional Name

guanfacine

CAS Registry Number

29110-47-2

SMILES

NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl

InChI Identifier

InChI=1S/C9H9Cl2N3O/c10-6-2-1-3-7(11)5(6)4-8(15)14-9(12)13/h1-3H,4H2,(H4,12,13,14,15)

InChI Key

INJOMKTZOLKMBF-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 chloride
Aryl halide
Carboximidamide
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Imine
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

acetamides (CHEBI:5558 )

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

Membrane (HMDB: HMDB0015153)

Source

Exogenous

Exogenous (HMDB: HMDB0015153)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	225 - 227 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.14 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.28	ALOGPS
logP	1.74	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.94	ChemAxon
pKa (Strongest Basic)	6.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.63 m³·mol⁻¹	ChemAxon
Polarizability	21.75 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]+	149.928	30932474
DeepCCS	[M-H]-	147.57	30932474
DeepCCS	[M-2H]-	181.43	30932474
DeepCCS	[M+Na]+	156.227	30932474
AllCCS	[M+H]+	149.6	32859911
AllCCS	[M+H-H2O]+	145.9	32859911
AllCCS	[M+NH4]+	153.0	32859911
AllCCS	[M+Na]+	154.0	32859911
AllCCS	[M-H]-	147.7	32859911
AllCCS	[M+Na-2H]-	148.3	32859911
AllCCS	[M+HCOO]-	149.0	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.	1.66 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7312 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	60.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1345.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	365.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	111.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	223.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	107.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	332.2 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	374.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	897.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	363.8 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	1071.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	419.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	145.6 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	26.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Guanfacine	NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl	3452.5	Standard polar	33892256
Guanfacine	NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl	1807.9	Standard non polar	33892256
Guanfacine	NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl	2176.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Guanfacine,1TMS,isomer #1	C[Si](C)(C)NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl	2390.1	Semi standard non polar	33892256
Guanfacine,1TMS,isomer #1	C[Si](C)(C)NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl	2101.0	Standard non polar	33892256
Guanfacine,1TMS,isomer #1	C[Si](C)(C)NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl	3900.0	Standard polar	33892256
Guanfacine,1TMS,isomer #2	C[Si](C)(C)N=C(N)NC(=O)CC1=C(Cl)C=CC=C1Cl	2181.9	Semi standard non polar	33892256
Guanfacine,1TMS,isomer #2	C[Si](C)(C)N=C(N)NC(=O)CC1=C(Cl)C=CC=C1Cl	2052.0	Standard non polar	33892256
Guanfacine,1TMS,isomer #2	C[Si](C)(C)N=C(N)NC(=O)CC1=C(Cl)C=CC=C1Cl	3781.5	Standard polar	33892256
Guanfacine,1TMS,isomer #3	C[Si](C)(C)N(C(=N)N)C(=O)CC1=C(Cl)C=CC=C1Cl	2250.9	Semi standard non polar	33892256
Guanfacine,1TMS,isomer #3	C[Si](C)(C)N(C(=N)N)C(=O)CC1=C(Cl)C=CC=C1Cl	2142.4	Standard non polar	33892256
Guanfacine,1TMS,isomer #3	C[Si](C)(C)N(C(=N)N)C(=O)CC1=C(Cl)C=CC=C1Cl	3837.4	Standard polar	33892256
Guanfacine,2TMS,isomer #1	C[Si](C)(C)N(C(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2354.6	Semi standard non polar	33892256
Guanfacine,2TMS,isomer #1	C[Si](C)(C)N(C(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2307.1	Standard non polar	33892256
Guanfacine,2TMS,isomer #1	C[Si](C)(C)N(C(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	3410.4	Standard polar	33892256
Guanfacine,2TMS,isomer #2	C[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C	2285.8	Semi standard non polar	33892256
Guanfacine,2TMS,isomer #2	C[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C	2012.9	Standard non polar	33892256
Guanfacine,2TMS,isomer #2	C[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C	3515.7	Standard polar	33892256
Guanfacine,2TMS,isomer #3	C[Si](C)(C)NC(=N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2290.8	Semi standard non polar	33892256
Guanfacine,2TMS,isomer #3	C[Si](C)(C)NC(=N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2238.8	Standard non polar	33892256
Guanfacine,2TMS,isomer #3	C[Si](C)(C)NC(=N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	3359.5	Standard polar	33892256
Guanfacine,2TMS,isomer #4	C[Si](C)(C)N=C(N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2190.4	Semi standard non polar	33892256
Guanfacine,2TMS,isomer #4	C[Si](C)(C)N=C(N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2097.1	Standard non polar	33892256
Guanfacine,2TMS,isomer #4	C[Si](C)(C)N=C(N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	3534.3	Standard polar	33892256
Guanfacine,3TMS,isomer #1	C[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C	2300.5	Semi standard non polar	33892256
Guanfacine,3TMS,isomer #1	C[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C	2093.8	Standard non polar	33892256
Guanfacine,3TMS,isomer #1	C[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C)[Si](C)(C)C	3111.4	Standard polar	33892256
Guanfacine,3TMS,isomer #2	C[Si](C)(C)N(C(=N)N([Si](C)(C)C)[Si](C)(C)C)C(=O)CC1=C(Cl)C=CC=C1Cl	2287.3	Semi standard non polar	33892256
Guanfacine,3TMS,isomer #2	C[Si](C)(C)N(C(=N)N([Si](C)(C)C)[Si](C)(C)C)C(=O)CC1=C(Cl)C=CC=C1Cl	2417.5	Standard non polar	33892256
Guanfacine,3TMS,isomer #2	C[Si](C)(C)N(C(=N)N([Si](C)(C)C)[Si](C)(C)C)C(=O)CC1=C(Cl)C=CC=C1Cl	3061.3	Standard polar	33892256
Guanfacine,3TMS,isomer #3	C[Si](C)(C)N=C(N[Si](C)(C)C)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2239.8	Semi standard non polar	33892256
Guanfacine,3TMS,isomer #3	C[Si](C)(C)N=C(N[Si](C)(C)C)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2041.3	Standard non polar	33892256
Guanfacine,3TMS,isomer #3	C[Si](C)(C)N=C(N[Si](C)(C)C)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	3007.3	Standard polar	33892256
Guanfacine,4TMS,isomer #1	C[Si](C)(C)N=C(N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2323.9	Semi standard non polar	33892256
Guanfacine,4TMS,isomer #1	C[Si](C)(C)N=C(N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2228.9	Standard non polar	33892256
Guanfacine,4TMS,isomer #1	C[Si](C)(C)N=C(N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2626.5	Standard polar	33892256
Guanfacine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl	2662.6	Semi standard non polar	33892256
Guanfacine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl	2350.2	Standard non polar	33892256
Guanfacine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl	3715.1	Standard polar	33892256
Guanfacine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N)NC(=O)CC1=C(Cl)C=CC=C1Cl	2494.5	Semi standard non polar	33892256
Guanfacine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N)NC(=O)CC1=C(Cl)C=CC=C1Cl	2273.2	Standard non polar	33892256
Guanfacine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N)NC(=O)CC1=C(Cl)C=CC=C1Cl	3750.6	Standard polar	33892256
Guanfacine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=N)N)C(=O)CC1=C(Cl)C=CC=C1Cl	2469.3	Semi standard non polar	33892256
Guanfacine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=N)N)C(=O)CC1=C(Cl)C=CC=C1Cl	2371.8	Standard non polar	33892256
Guanfacine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=N)N)C(=O)CC1=C(Cl)C=CC=C1Cl	3761.0	Standard polar	33892256
Guanfacine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2782.5	Semi standard non polar	33892256
Guanfacine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2700.3	Standard non polar	33892256
Guanfacine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=N)NC(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	3298.2	Standard polar	33892256
Guanfacine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C(C)(C)C	2764.5	Semi standard non polar	33892256
Guanfacine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C(C)(C)C	2402.0	Standard non polar	33892256
Guanfacine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N[Si](C)(C)C(C)(C)C	3319.9	Standard polar	33892256
Guanfacine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2724.6	Semi standard non polar	33892256
Guanfacine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2657.3	Standard non polar	33892256
Guanfacine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	3254.8	Standard polar	33892256
Guanfacine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2650.7	Semi standard non polar	33892256
Guanfacine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2496.4	Standard non polar	33892256
Guanfacine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(N)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	3502.0	Standard polar	33892256
Guanfacine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2973.1	Semi standard non polar	33892256
Guanfacine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2639.5	Standard non polar	33892256
Guanfacine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(NC(=O)CC1=C(Cl)C=CC=C1Cl)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3128.7	Standard polar	33892256
Guanfacine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)CC1=C(Cl)C=CC=C1Cl	2938.8	Semi standard non polar	33892256
Guanfacine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)CC1=C(Cl)C=CC=C1Cl	2970.4	Standard non polar	33892256
Guanfacine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)CC1=C(Cl)C=CC=C1Cl	3128.1	Standard polar	33892256
Guanfacine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2897.4	Semi standard non polar	33892256
Guanfacine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2562.3	Standard non polar	33892256
Guanfacine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	3079.1	Standard polar	33892256
Guanfacine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3146.2	Semi standard non polar	33892256
Guanfacine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2955.4	Standard non polar	33892256
Guanfacine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N(C(=O)CC1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2896.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Guanfacine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-5900000000-766dd9f92ab525fb3d7f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guanfacine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 10V, Positive-QTOF	splash10-0002-2190000000-f396a1e8e135a8e36357	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 20V, Positive-QTOF	splash10-06ri-2940000000-5a7460d90b0e4e64ca27	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 40V, Positive-QTOF	splash10-0a4i-5900000000-722b0c3c89afd7b7ebab	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 10V, Negative-QTOF	splash10-0006-3190000000-3e0c32003f6e9cdb1622	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 20V, Negative-QTOF	splash10-0zfu-8590000000-95737b8dd85b7d5f0970	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 40V, Negative-QTOF	splash10-0006-9100000000-e0d6699b8eaef7231c16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 10V, Positive-QTOF	splash10-0002-3090000000-90afd0b6edebed6386b7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 20V, Positive-QTOF	splash10-01ox-9000000000-17eb76d0d1e99836e557	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 40V, Positive-QTOF	splash10-0a4l-4900000000-680156efc4df06b145b6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 10V, Negative-QTOF	splash10-0f6x-0190000000-02a925b95a2650e92658	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 20V, Negative-QTOF	splash10-0pc3-2960000000-ec4836343fd084b9aa0c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guanfacine 40V, Negative-QTOF	splash10-0006-9200000000-9b0988ced8204ad0f3fc	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 DB01018	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01018	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01018

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3399

KEGG Compound ID

C07037

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Guanfacine

METLIN ID

Not Available

PubChem Compound

3519

PDB ID

Not Available

ChEBI ID

166029

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 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Clement B, Demesmaeker M: Microsomal catalyzed N-hydroxylation of guanfacine and reduction of N-hydroxyguanfacine. Arch Pharm (Weinheim). 1997 Oct;330(9-10):303-6. [PubMed:9396389 ]
Guillouzo A, Le Bigot JF, Guguen-Guillouzo C, Kiechel JR: Presence of phase I and phase II drug metabolizing enzymes in cultured human foetal hepatocytes. Biochem Pharmacol. 1982 Jul 15;31(14):2427-30. [PubMed:6751332 ]

Enzyme Details

2. Cytochrome P450 2C9

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

Clement B, Demesmaeker M: Microsomal catalyzed N-hydroxylation of guanfacine and reduction of N-hydroxyguanfacine. Arch Pharm (Weinheim). 1997 Oct;330(9-10):303-6. [PubMed:9396389 ]
Guillouzo A, Le Bigot JF, Guguen-Guillouzo C, Kiechel JR: Presence of phase I and phase II drug metabolizing enzymes in cultured human foetal hepatocytes. Biochem Pharmacol. 1982 Jul 15;31(14):2427-30. [PubMed:6751332 ]

Enzyme Details

3. Cytochrome P450 2C19

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

Clement B, Demesmaeker M: Microsomal catalyzed N-hydroxylation of guanfacine and reduction of N-hydroxyguanfacine. Arch Pharm (Weinheim). 1997 Oct;330(9-10):303-6. [PubMed:9396389 ]
Guillouzo A, Le Bigot JF, Guguen-Guillouzo C, Kiechel JR: Presence of phase I and phase II drug metabolizing enzymes in cultured human foetal hepatocytes. Biochem Pharmacol. 1982 Jul 15;31(14):2427-30. [PubMed:6751332 ]

Enzyme Details

4. 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

Avery RA, Franowicz JS, Studholme C, van Dyck CH, Arnsten AF: The alpha-2A-adrenoceptor agonist, guanfacine, increases regional cerebral blood flow in dorsolateral prefrontal cortex of monkeys performing a spatial working memory task. Neuropsychopharmacology. 2000 Sep;23(3):240-9. [PubMed:10942848 ]
Sagvolden T: The alpha-2A adrenoceptor agonist guanfacine improves sustained attention and reduces overactivity and impulsiveness in an animal model of Attention-Deficit/Hyperactivity Disorder (ADHD). Behav Brain Funct. 2006 Dec 15;2:41. [PubMed:17173664 ]
Yuan R, Wu Z, Kostenyuk IA, Burns JK: G-protein-coupled alpha2A-adrenoreceptor agonists differentially alter citrus leaf and fruit abscission by affecting expression of ACC synthase and ACC oxidase. J Exp Bot. 2005 Jul;56(417):1867-75. Epub 2005 May 31. [PubMed:15928018 ]
Birnbaum SG, Podell DM, Arnsten AF: Noradrenergic alpha-2 receptor agonists reverse working memory deficits induced by the anxiogenic drug, FG7142, in rats. Pharmacol Biochem Behav. 2000 Nov;67(3):397-403. [PubMed:11164065 ]
Millan MJ: Evidence that an alpha 2A-adrenoceptor subtype mediates antinociception in mice. Eur J Pharmacol. 1992 May 14;215(2-3):355-6. [PubMed:1356794 ]
Stahl SM: Mechanism of action of alpha 2A-adrenergic agonists in attention-deficit/hyperactivity disorder with or without oppositional symptoms. J Clin Psychiatry. 2010 Mar;71(3):223-4. doi: 10.4088/JCP.09bs05899pur. [PubMed:20331927 ]

Showing metabocard for Guanfacine (HMDB0015153)

MOL for HMDB0015153 (Guanfacine)

3D MOL for HMDB0015153 (Guanfacine)

3D SDF for HMDB0015153 (Guanfacine)

3D-SDF for HMDB0015153 (Guanfacine)

PDB for HMDB0015153 (Guanfacine)

3D PDB for HMDB0015153 (Guanfacine)

SMILES for HMDB0015153 (Guanfacine)

INCHI for HMDB0015153 (Guanfacine)

Structure for HMDB0015153 (Guanfacine)

3D Structure for HMDB0015153 (Guanfacine)

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