NP-MRD: Showing NP-Card for baclofen (NP0257624)

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Record Information

Version

2.0

Created at

2022-09-07 22:48:01 UTC

Updated at

2022-09-07 22:48:01 UTC

NP-MRD ID

NP0257624

Secondary Accession Numbers

None

Natural Product Identification

Common Name

baclofen

Description

Baclofen, also known as (+-)-baclofen or gen baclofen, 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. Baclofen is a very strong basic compound (based on its pKa). baclofen is found in Streptomyces halstedii. baclofen was first documented in 2001 (PMID: 11168554). Baclofen is a potentially toxic compound (PMID: 18225966) (PMID: 11772961) (PMID: 18682277).

Structure

MOL 3D MOL SDF 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>
NP0257624

> <DATABASE_NAME>
NP-MRD

> <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

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	HMDB
Alphapharm brand OF baclofen	HMDB
Ashbourne brand OF baclofen	HMDB
Baclofen athena brand	HMDB
Baclofen irex brand	HMDB
Baclospas	HMDB
Chlorophenyl gaba	HMDB
Ciba geigy brand OF baclofen	HMDB
Gen baclofen	HMDB
GenBaclofen	HMDB
Isis brand OF baclofen	HMDB
PCP-GABA	HMDB
AWD, baclofen	HMDB
Athena brand OF baclofen	HMDB
Atrofen	HMDB
Baclofen apotex brand	HMDB
Baclofen isis brand	HMDB
Baclofen medtronic brand	HMDB
Baclofen nu-pharm brand	HMDB
Baclofen pharmascience brand	HMDB
NuBaclo	HMDB
PMS-Baclofen	HMDB
PMSBaclofen	HMDB
Apo baclofen	HMDB
ApoBaclofen	HMDB
Apotex brand OF baclofen	HMDB
Baclofen awd	HMDB
Baclofen ciba-geigy brand	HMDB
Baclofen novartis brand	HMDB
Baclofène irex	HMDB
Baclofène-irex	HMDB
BaclofèneIrex	HMDB
CIBA-34,647-ba	HMDB
Gen-baclofen	HMDB
Irex brand OF baclofen	HMDB
Lebic	HMDB
Nu baclo	HMDB
Nu-baclo	HMDB
Nu-pharm brand OF baclofen	HMDB
PMS Baclofen	HMDB
Apo-baclofen	HMDB
Baclofen alphapharm brand	HMDB
Baclofen ashbourne brand	HMDB
Baclophen	HMDB
CIBA34,647ba	HMDB
Ciba-geigy brand OF baclofen	HMDB
Clofen	HMDB
GABA, chlorophenyl	HMDB
Genpharm	HMDB
Liorésal	HMDB
Medtronic brand OF baclofen	HMDB
Novartis brand OF baclofen	HMDB
Nu pharm brand OF baclofen	HMDB
Pharmascience brand OF baclofen	HMDB

Chemical Formula

C₁₀H₁₂ClNO₂

Average Mass

213.6610 Da

Monoisotopic Mass

213.05566 Da

IUPAC Name

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

Traditional Name

baclofen

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces halstedii	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0014327

DrugBank ID

DB00181

Phenol Explorer Compound ID

Not Available

FoodDB 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

2284

PDB ID

Not Available

ChEBI ID

2972

Good Scents ID

Not Available

References

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. doi: 10.1046/j.1460-9568.2001.01410.x. [PubMed:11168554 ]
See S, Ginzburg R: Skeletal muscle relaxants. Pharmacotherapy. 2008 Feb;28(2):207-13. doi: 10.1592/phco.28.2.207. [PubMed:18225966 ]
Zhang Q, Lehmann A, Rigda R, Dent J, Holloway RH: Control of transient lower oesophageal sphincter relaxations and reflux by the GABA(B) agonist baclofen in patients with gastro-oesophageal reflux disease. Gut. 2002 Jan;50(1):19-24. doi: 10.1136/gut.50.1.19. [PubMed:11772961 ]
Le Foll B, Wertheim CE, Goldberg SR: Effects of baclofen on conditioned rewarding and discriminative stimulus effects of nicotine in rats. Neurosci Lett. 2008 Oct 10;443(3):236-40. doi: 10.1016/j.neulet.2008.07.074. Epub 2008 Aug 5. [PubMed:18682277 ]
LOTUS database [Link]

Showing NP-Card for baclofen (NP0257624)

MOL for NP0257624 (baclofen)

3D MOL for NP0257624 (baclofen)

3D SDF for NP0257624 (baclofen)

3D-SDF for NP0257624 (baclofen)

PDB for NP0257624 (baclofen)

3D PDB for NP0257624 (baclofen)

SMILES for NP0257624 (baclofen)

INCHI for NP0257624 (baclofen)

Structure for NP0257624 (baclofen)

3D Structure for NP0257624 (baclofen)