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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0014327

Secondary Accession Numbers

HMDB14327

Metabolite Identification

Common Name

Baclofen

Description

Baclofen is a gamma-amino-butyric acid (GABA) derivative used as a skeletal muscle relaxant. Baclofen stimulates GABA-B receptors leading to decreased frequency and amplitude of muscle spasms. It is especially useful in treating muscle spasticity associated with spinal cord injury. It appears to act primarily at the spinal cord level by inhibiting spinal polysynaptic afferent pathways and, to a lesser extent, monosynaptic afferent pathways.

Structure

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

181
  Mrv0541 02231214302D          

 14 14  0  0  1  0            999 V2000
    3.5220   -2.7308    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.2193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.2193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 12 14  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014327

> <DATABASE_NAME>
hmdb

> <SMILES>
NCC(CC(O)=O)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12ClNO2/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14/h1-4,8H,5-6,12H2,(H,13,14)

> <INCHI_KEY>
KPYSYYIEGFHWSV-UHFFFAOYSA-N

> <FORMULA>
C10H12ClNO2

> <MOLECULAR_WEIGHT>
213.661

> <EXACT_MASS>
213.05565634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.126856164006483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-3-(4-chlorophenyl)butanoic acid

> <ALOGPS_LOGP>
-0.82

> <JCHEM_LOGP>
-0.7824002601230235

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.88689479330878

> <JCHEM_PKA_STRONGEST_BASIC>
9.792014945506153

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
54.82920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
baclofen

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 181                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       6.574  -5.097   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       9.242   4.143   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.574   4.143   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.907   1.063   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.574   1.063   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -0.477   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.908   1.833   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241   1.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -1.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -1.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908   3.373   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.908  -2.787   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241  -2.787   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -3.557   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    8                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5    9   10                                                  
CONECT    7    5   11                                                       
CONECT    8    4    5                                                       
CONECT    9    6   12                                                       
CONECT   10    6   13                                                       
CONECT   11    2    3    7                                                  
CONECT   12    9   14                                                       
CONECT   13   10   14                                                       
CONECT   14    1   12   13                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+-)-Baclofen	ChEBI
4-Amino-3-(4-chlorophenyl)butyric acid	ChEBI
Baclofene	ChEBI
Baclofeno	ChEBI
Baclofenum	ChEBI
beta-(4-Chlorophenyl)gaba	ChEBI
beta-(Aminomethyl)-4-chlorobenzenepropanoic acid	ChEBI
beta-(Aminomethyl)-p-chlorohydrocinnamic acid	ChEBI
beta-(p-Chlorophenyl)-gamma-aminobutyric acid	ChEBI
DL-4-Amino-3-p-chlorophenylbutanoic acid	ChEBI
DL-Baclofen	ChEBI
gamma-Amino-beta-(p-chlorophenyl)butyric acid	ChEBI
Kemstro	Kegg
Lioresal	Kegg
4-Amino-3-(4-chlorophenyl)butyrate	Generator
b-(4-Chlorophenyl)gaba	Generator
Β-(4-chlorophenyl)gaba	Generator
b-(Aminomethyl)-4-chlorobenzenepropanoate	Generator
b-(Aminomethyl)-4-chlorobenzenepropanoic acid	Generator
beta-(Aminomethyl)-4-chlorobenzenepropanoate	Generator
Β-(aminomethyl)-4-chlorobenzenepropanoate	Generator
Β-(aminomethyl)-4-chlorobenzenepropanoic acid	Generator
b-(Aminomethyl)-p-chlorohydrocinnamate	Generator
b-(Aminomethyl)-p-chlorohydrocinnamic acid	Generator
beta-(Aminomethyl)-p-chlorohydrocinnamate	Generator
Β-(aminomethyl)-p-chlorohydrocinnamate	Generator
Β-(aminomethyl)-p-chlorohydrocinnamic acid	Generator
b-(p-Chlorophenyl)-g-aminobutyrate	Generator
b-(p-Chlorophenyl)-g-aminobutyric acid	Generator
beta-(p-Chlorophenyl)-gamma-aminobutyrate	Generator
Β-(p-chlorophenyl)-γ-aminobutyrate	Generator
Β-(p-chlorophenyl)-γ-aminobutyric acid	Generator
DL-4-Amino-3-p-chlorophenylbutanoate	Generator
g-Amino-b-(p-chlorophenyl)butyrate	Generator
g-Amino-b-(p-chlorophenyl)butyric acid	Generator
gamma-Amino-beta-(p-chlorophenyl)butyrate	Generator
Γ-amino-β-(p-chlorophenyl)butyrate	Generator
Γ-amino-β-(p-chlorophenyl)butyric acid	Generator
ASTA medica brand OF baclofen	MeSH, HMDB
Alphapharm brand OF baclofen	MeSH, HMDB
Ashbourne brand OF baclofen	MeSH, HMDB
Baclofen athena brand	MeSH, HMDB
Baclofen irex brand	MeSH, HMDB
Baclospas	MeSH, HMDB
Chlorophenyl gaba	MeSH, HMDB
Ciba geigy brand OF baclofen	MeSH, HMDB
Gen baclofen	MeSH, HMDB
GenBaclofen	MeSH, HMDB
Isis brand OF baclofen	MeSH, HMDB
PCP-GABA	MeSH, HMDB
AWD, baclofen	MeSH, HMDB
Athena brand OF baclofen	MeSH, HMDB
Atrofen	MeSH, HMDB
Baclofen apotex brand	MeSH, HMDB
Baclofen isis brand	MeSH, HMDB
Baclofen medtronic brand	MeSH, HMDB
Baclofen nu-pharm brand	MeSH, HMDB
Baclofen pharmascience brand	MeSH, HMDB
NuBaclo	MeSH, HMDB
PMS-Baclofen	MeSH, HMDB
PMSBaclofen	MeSH, HMDB
apo Baclofen	MeSH, HMDB
ApoBaclofen	MeSH, HMDB
Apotex brand OF baclofen	MeSH, HMDB
Baclofen awd	MeSH, HMDB
Baclofen ciba-geigy brand	MeSH, HMDB
Baclofen novartis brand	MeSH, HMDB
Baclofène irex	MeSH, HMDB
Baclofène-irex	MeSH, HMDB
BaclofèneIrex	MeSH, HMDB
CIBA-34,647-ba	MeSH, HMDB
Gen-baclofen	MeSH, HMDB
Irex brand OF baclofen	MeSH, HMDB
Lebic	MeSH, HMDB
Nu baclo	MeSH, HMDB
Nu-baclo	MeSH, HMDB
Nu-pharm brand OF baclofen	MeSH, HMDB
PMS Baclofen	MeSH, HMDB
apo-Baclofen	MeSH, HMDB
Baclofen alphapharm brand	MeSH, HMDB
Baclofen ashbourne brand	MeSH, HMDB
Baclophen	MeSH, HMDB
CIBA34,647ba	MeSH, HMDB
Ciba-geigy brand OF baclofen	MeSH, HMDB
Clofen	MeSH, HMDB
GABA, chlorophenyl	MeSH, HMDB
Genpharm	MeSH, HMDB
Medtronic brand OF baclofen	MeSH, HMDB
Novartis brand OF baclofen	MeSH, HMDB
Nu pharm brand OF baclofen	MeSH, HMDB
Pharmascience brand OF baclofen	MeSH, HMDB

Chemical Formula

C₁₀H₁₂ClNO₂

Average Molecular Weight

213.661

Monoisotopic Molecular Weight

213.05565634

IUPAC Name

4-amino-3-(4-chlorophenyl)butanoic acid

Traditional Name

baclofen

CAS Registry Number

1134-47-0

SMILES

NCC(CC(O)=O)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C10H12ClNO2/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14/h1-4,8H,5-6,12H2,(H,13,14)

InChI Key

KPYSYYIEGFHWSV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
3-phenylpropanoic-acid
Amino fatty acid
Chlorobenzene
Aralkylamine
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organohalogen compound
Organic nitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Amine
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:2972 )
primary amino compound (CHEBI:2972 )
monochlorobenzenes (CHEBI:2972 )
gamma-amino acid (CHEBI:2972 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0243670)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	206 - 208 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.71 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	149.2	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.71 g/L	ALOGPS
logP	-0.82	ALOGPS
logP	-0.78	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.83 m³·mol⁻¹	ChemAxon
Polarizability	21.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	143.268	30932474
DeepCCS	[M-H]-	140.91	30932474
DeepCCS	[M-2H]-	175.962	30932474
DeepCCS	[M+Na]+	150.781	30932474
AllCCS	[M+H]+	145.2	32859911
AllCCS	[M+H-H2O]+	141.3	32859911
AllCCS	[M+NH4]+	148.9	32859911
AllCCS	[M+Na]+	149.9	32859911
AllCCS	[M-H]-	145.4	32859911
AllCCS	[M+Na-2H]-	146.1	32859911
AllCCS	[M+HCOO]-	147.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Baclofen	NCC(CC(O)=O)C1=CC=C(Cl)C=C1	3020.1	Standard polar	33892256
Baclofen	NCC(CC(O)=O)C1=CC=C(Cl)C=C1	1846.3	Standard non polar	33892256
Baclofen	NCC(CC(O)=O)C1=CC=C(Cl)C=C1	1902.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Baclofen,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC(CN)C1=CC=C(Cl)C=C1	1860.6	Semi standard non polar	33892256
Baclofen,1TMS,isomer #2	C[Si](C)(C)NCC(CC(=O)O)C1=CC=C(Cl)C=C1	1985.1	Semi standard non polar	33892256
Baclofen,2TMS,isomer #1	C[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C)C1=CC=C(Cl)C=C1	1956.9	Semi standard non polar	33892256
Baclofen,2TMS,isomer #1	C[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C)C1=CC=C(Cl)C=C1	1938.6	Standard non polar	33892256
Baclofen,2TMS,isomer #1	C[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C)C1=CC=C(Cl)C=C1	2308.9	Standard polar	33892256
Baclofen,2TMS,isomer #2	C[Si](C)(C)N(CC(CC(=O)O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2167.6	Semi standard non polar	33892256
Baclofen,2TMS,isomer #2	C[Si](C)(C)N(CC(CC(=O)O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2116.7	Standard non polar	33892256
Baclofen,2TMS,isomer #2	C[Si](C)(C)N(CC(CC(=O)O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2483.8	Standard polar	33892256
Baclofen,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=C(Cl)C=C1	2141.1	Semi standard non polar	33892256
Baclofen,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=C(Cl)C=C1	2130.8	Standard non polar	33892256
Baclofen,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=C(Cl)C=C1	2247.2	Standard polar	33892256
Baclofen,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(CN)C1=CC=C(Cl)C=C1	2115.2	Semi standard non polar	33892256
Baclofen,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC(CC(=O)O)C1=CC=C(Cl)C=C1	2238.7	Semi standard non polar	33892256
Baclofen,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(Cl)C=C1	2456.7	Semi standard non polar	33892256
Baclofen,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(Cl)C=C1	2396.0	Standard non polar	33892256
Baclofen,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(Cl)C=C1	2523.9	Standard polar	33892256
Baclofen,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(CC(=O)O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2616.3	Semi standard non polar	33892256
Baclofen,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(CC(=O)O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2483.5	Standard non polar	33892256
Baclofen,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(CC(=O)O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2617.3	Standard polar	33892256
Baclofen,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=C(Cl)C=C1	2831.8	Semi standard non polar	33892256
Baclofen,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=C(Cl)C=C1	2702.3	Standard non polar	33892256
Baclofen,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=C(Cl)C=C1	2544.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Baclofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9600000000-6ae6d753213a9472b32c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Baclofen GC-MS (1 TMS) - 70eV, Positive	splash10-0ff0-9720000000-6949ab5f0b56c63b916a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Baclofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Baclofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Baclofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Baclofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Baclofen GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-2900000000-963f049a4367a1d5a5f5	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen LC-ESI-QTOF , negative-QTOF	splash10-03dr-0950000000-33d21cbb6740c1f1aee1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen LC-ESI-QQ , positive-QTOF	splash10-03di-1590000000-8a64733764308ba98f9a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen LC-ESI-QQ , positive-QTOF	splash10-0f6t-0900000000-6647c58db763b4df68a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen LC-ESI-QQ , positive-QTOF	splash10-0udi-0900000000-72d6d878c9c2f29d846a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen LC-ESI-QQ , positive-QTOF	splash10-014i-1900000000-18f69033596a03ee643a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen LC-ESI-QQ , positive-QTOF	splash10-014i-1900000000-997473c303f07afcdf4e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen LC-ESI-IT , positive-QTOF	splash10-0002-0900000000-d1da4625d180fe0af521	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen LC-ESI-QTOF , positive-QTOF	splash10-03di-0190000000-bd0fff49defde62ed0fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen LC-ESI-QTOF , positive-QTOF	splash10-0ik9-0790000000-1a50b0b7f24aaaf6a87e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Baclofen 30V, Positive-QTOF	splash10-0ik9-0890000000-3f3794cee3f3ce674c85	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 10V, Negative-QTOF	splash10-03xr-0690000000-4dd9b649eccb58c3cef0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 20V, Negative-QTOF	splash10-03xr-0940000000-08d03c01d7cee16a2833	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 40V, Negative-QTOF	splash10-0ikl-1900000000-69e953c6f51f0939e70c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 10V, Negative-QTOF	splash10-03xu-0920000000-6858869b9cb96b03630e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 20V, Negative-QTOF	splash10-0gw0-1900000000-3a4e75e8e4356199aa50	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 40V, Negative-QTOF	splash10-0gx0-9800000000-bf4ef0f5f1c595bcb485	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 10V, Positive-QTOF	splash10-01ot-0930000000-4c6fbeef09787ebe54c8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 20V, Positive-QTOF	splash10-016s-0900000000-904b104c639269bfe4f1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 40V, Positive-QTOF	splash10-000i-1900000000-62cafb0d9fec846e47b9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 10V, Positive-QTOF	splash10-0udj-0900000000-cd340e3600f88734f280	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 20V, Positive-QTOF	splash10-0udi-0900000000-89fb1deb3a2cc738679c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Baclofen 40V, Positive-QTOF	splash10-0mmr-1900000000-62e1c901d161ea96465b	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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 DB00181	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00181	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2197

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Baclofen

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

2972

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

Mezler M, Muller T, Raming K: Cloning and functional expression of GABA(B) receptors from Drosophila. Eur J Neurosci. 2001 Feb;13(3):477-86. [PubMed:11168554 ]
Dzitoyeva S, Dimitrijevic N, Manev H: Gamma-aminobutyric acid B receptor 1 mediates behavior-impairing actions of alcohol in Drosophila: adult RNA interference and pharmacological evidence. Proc Natl Acad Sci U S A. 2003 Apr 29;100(9):5485-90. Epub 2003 Apr 11. [PubMed:12692303 ]
See S, Ginzburg R: Skeletal muscle relaxants. Pharmacotherapy. 2008 Feb;28(2):207-13. doi: 10.1592/phco.28.2.207. [PubMed:18225966 ]

Enzymes

Enzyme Details

1. Gamma-aminobutyric acid type B receptor subunit 1

General function:: Involved in G-protein coupled receptor activity
Specific function:: Isoform 1E function may be to regulate the availability of functional GABA-B-R1A/GABA-B-R2 heterodimers by competing for GABA-B-R2 dimerization. This could explain the observation that certain small molecule ligands exhibit differential affinity for central versus peripheral sites
Gene Name:: GABBR1
Uniprot ID:: Q9UBS5
Molecular weight:: 108319.4

References

Bowery NG: GABAB receptor pharmacology. Annu Rev Pharmacol Toxicol. 1993;33:109-47. [PubMed:8388192 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Garcia-Gil L, de Miguel R, Romero J, Perez A, Ramos JA, Fernandez-Ruiz JJ: Perinatal delta9-tetrahydrocannabinol exposure augmented the magnitude of motor inhibition caused by GABA(B), but not GABA(A), receptor agonists in adult rats. Neurotoxicol Teratol. 1999 May-Jun;21(3):277-83. [PubMed:10386831 ]
Lehmann A: GABAB receptors as drug targets to treat gastroesophageal reflux disease. Pharmacol Ther. 2009 Jun;122(3):239-45. doi: 10.1016/j.pharmthera.2009.02.008. Epub 2009 Mar 19. [PubMed:19303900 ]
Motalli R, Louvel J, Tancredi V, Kurcewicz I, Wan-Chow-Wah D, Pumain R, Avoli M: GABA(B) receptor activation promotes seizure activity in the juvenile rat hippocampus. J Neurophysiol. 1999 Aug;82(2):638-47. [PubMed:10444662 ]
Mott DD, Li Q, Okazaki MM, Turner DA, Lewis DV: GABAB-Receptor-mediated currents in interneurons of the dentate-hilus border. J Neurophysiol. 1999 Sep;82(3):1438-50. [PubMed:10482760 ]
Ogasawara T, Itoh Y, Tamura M, Mushiroi T, Ukai Y, Kise M, Kimura K: Involvement of cholinergic and GABAergic systems in the reversal of memory disruption by NS-105, a cognition enhancer. Pharmacol Biochem Behav. 1999 Sep;64(1):41-52. [PubMed:10494996 ]
Pittman QJ: The action is at the terminal. J Physiol. 1999 Nov 1;520 Pt 3:629. [PubMed:10545129 ]
Stringer JL, Lorenzo N: The reduction in paired-pulse inhibition in the rat hippocampus by gabapentin is independent of GABA(B) receptor receptor activation. Epilepsy Res. 1999 Feb;33(2-3):169-76. [PubMed:10094428 ]

Enzyme Details

2. Gamma-aminobutyric acid type B receptor subunit 2

General function:: Involved in G-protein coupled receptor activity
Specific function:: Receptor for GABA. The activity of this receptor is mediated by G-proteins that inhibit adenylyl cyclase activity, stimulates phospholipase A2, activates potassium channels, inactivates voltage-dependent calcium-channels and modulates inositol phospholipids hydrolysis. Plays a critical role in the fine-tuning of inhibitory synaptic transmission. Pre-synaptic GABA-B-R inhibit neurotransmitter release by down-regulating high- voltage activated calcium channels, whereas postsynaptic GABA-B-R decrease neuronal excitability by activating a prominent inwardly rectifying potassium (Kir) conductance that underlies the late inhibitory postsynaptic potentials. Not only implicated in synaptic inhibition but also in hippocampal long-term potentiation, slow wave sleep, muscle relaxation and antinociception
Gene Name:: GABBR2
Uniprot ID:: O75899
Molecular weight:: 105820.5

References

Belley M, Sullivan R, Reeves A, Evans J, O'Neill G, Ng GY: Synthesis of the nanomolar photoaffinity GABA(B) receptor ligand CGP 71872 reveals diversity in the tissue distribution of GABA(B) receptor forms. Bioorg Med Chem. 1999 Dec;7(12):2697-704. [PubMed:10658574 ]
Braun M, Wendt A, Buschard K, Salehi A, Sewing S, Gromada J, Rorsman P: GABAB receptor activation inhibits exocytosis in rat pancreatic beta-cells by G-protein-dependent activation of calcineurin. J Physiol. 2004 Sep 1;559(Pt 2):397-409. Epub 2004 Jul 2. [PubMed:15235087 ]
Bowery NG: GABAB receptor pharmacology. Annu Rev Pharmacol Toxicol. 1993;33:109-47. [PubMed:8388192 ]
Filippov AK, Couve A, Pangalos MN, Walsh FS, Brown DA, Moss SJ: Heteromeric assembly of GABA(B)R1 and GABA(B)R2 receptor subunits inhibits Ca(2+) current in sympathetic neurons. J Neurosci. 2000 Apr 15;20(8):2867-74. [PubMed:10751439 ]
Lehmann A: GABAB receptors as drug targets to treat gastroesophageal reflux disease. Pharmacol Ther. 2009 Jun;122(3):239-45. doi: 10.1016/j.pharmthera.2009.02.008. Epub 2009 Mar 19. [PubMed:19303900 ]
Martin SC, Russek SJ, Farb DH: Molecular identification of the human GABABR2: cell surface expression and coupling to adenylyl cyclase in the absence of GABABR1. Mol Cell Neurosci. 1999 Mar;13(3):180-91. [PubMed:10328880 ]
Pittman QJ: The action is at the terminal. J Physiol. 1999 Nov 1;520 Pt 3:629. [PubMed:10545129 ]

Showing metabocard for Baclofen (HMDB0014327)

MOL for HMDB0014327 (Baclofen)

3D MOL for HMDB0014327 (Baclofen)

3D SDF for HMDB0014327 (Baclofen)

3D-SDF for HMDB0014327 (Baclofen)

PDB for HMDB0014327 (Baclofen)

3D PDB for HMDB0014327 (Baclofen)

SMILES for HMDB0014327 (Baclofen)

INCHI for HMDB0014327 (Baclofen)

Structure for HMDB0014327 (Baclofen)

3D Structure for HMDB0014327 (Baclofen)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References