Showing NP-Card for Methyl 4-aminobutyrate (NP0002663) (2024)

Record InformationVersion1.0Created at2020-11-23 18:26:21 UTCUpdated at2021-08-12 19:51:47 UTC NP-MRD IDNP0002663Secondary Accession NumbersNoneNatural Product IdentificationCommon NameMethyl 4-aminobutyrateProvided ByBMRB

DescriptionMethyl 4-aminobutanoate is also known as methyl 4-aminobutyric acid. It was first documented in 1986 (PMID: 3701787). Based on a literature review a small amount of articles have been published on methyl 4-aminobutanoate (PMID: 17984079) (PMID: 1673070).Structure

MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002663 (Methyl 4-aminobutyrate)

 RDKit 2D 19 18 0 0 0 0 0 0 0 0999 V2000 -4.1696 0.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6845 0.6548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7593 -0.5260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3193 -1.9175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2742 -0.3152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2109 -0.1043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6960 0.1065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1811 0.3173 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3804 1.9291 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9588 -1.0412 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6547 0.2331 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0634 -1.8003 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4850 1.1700 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4217 -1.5894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0001 1.3808 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4852 1.5916 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9068 -1.3786 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7411 1.7089 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1062 -0.8634 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 1 9 1 1 1 10 1 0 1 11 1 0 5 12 1 6 5 13 1 0 6 14 1 6 6 15 1 0 7 16 1 6 7 17 1 0 8 18 1 0 8 19 1 0M END

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3D MOL for NP0002663 (Methyl 4-aminobutyrate)

NP0002663 RDKit 3D 19 18 0 0 0 0 0 0 0 0999 V2000 2.7242 1.0135 -0.1728 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4267 0.4481 -0.2106 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1972 -0.8351 0.1840 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2064 -1.5042 0.5894 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0887 -1.5513 0.1991 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2577 -0.7406 -0.2499 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4922 0.4821 0.6096 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6454 1.2245 0.1160 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4924 0.2798 0.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0122 1.4029 -1.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7546 1.9092 0.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2404 -2.0107 1.1983 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0165 -2.4104 -0.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1262 -0.4910 -1.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1744 -1.3667 -0.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6102 1.1506 0.6597 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7202 0.2000 1.6582 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1236 0.6370 -0.6006 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3511 2.1621 -0.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 1 9 1 0 1 10 1 0 1 11 1 0 5 12 1 0 5 13 1 0 6 14 1 0 6 15 1 0 7 16 1 0 7 17 1 0 8 18 1 0 8 19 1 0M END

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3D SDF for NP0002663 (Methyl 4-aminobutyrate)

 RDKit 2D 19 18 0 0 0 0 0 0 0 0999 V2000 -4.1696 0.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6845 0.6548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7593 -0.5260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3193 -1.9175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2742 -0.3152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2109 -0.1043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6960 0.1065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1811 0.3173 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3804 1.9291 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9588 -1.0412 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6547 0.2331 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0634 -1.8003 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4850 1.1700 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4217 -1.5894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0001 1.3808 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4852 1.5916 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9068 -1.3786 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7411 1.7089 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1062 -0.8634 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 1 9 1 1 1 10 1 0 1 11 1 0 5 12 1 6 5 13 1 0 6 14 1 6 6 15 1 0 7 16 1 6 7 17 1 0 8 18 1 0 8 19 1 0M END> <DATABASE_ID>NP0002663> <DATABASE_NAME>NP-MRD> <SMILES>COC(=O)CCCN> <INCHI_IDENTIFIER>InChI=1S/C5H11NO2/c1-8-5(7)3-2-4-6/h2-4,6H2,1H3> <INCHI_KEY>KVQGGLZHHFGHPU-UHFFFAOYSA-N> <FORMULA>C5H11NO2> <MOLECULAR_WEIGHT>117.1463> <EXACT_MASS>117.078978601> <JCHEM_ACCEPTOR_COUNT>2> <JCHEM_AVERAGE_POLARIZABILITY>12.728464733410421> <JCHEM_BIOAVAILABILITY>1> <JCHEM_DONOR_COUNT>1> <JCHEM_FORMAL_CHARGE>0> <JCHEM_GHOSE_FILTER>0> <JCHEM_IUPAC>methyl 4-aminobutanoate> <ALOGPS_LOGP>-0.47> <JCHEM_LOGP>-0.47590755966666665> <ALOGPS_LOGS>0.38> <JCHEM_MDDR_LIKE_RULE>0> <JCHEM_NUMBER_OF_RINGS>0> <JCHEM_PHYSIOLOGICAL_CHARGE>1> <JCHEM_PKA_STRONGEST_BASIC>10.189780575000759> <JCHEM_POLAR_SURFACE_AREA>52.32000000000001> <JCHEM_REFRACTIVITY>30.2269> <JCHEM_ROTATABLE_BOND_COUNT>4> <JCHEM_RULE_OF_FIVE>1> <ALOGPS_SOLUBILITY>2.84e+02 g/l> <JCHEM_TRADITIONAL_IUPAC>methyl 4-aminobutanoate> <JCHEM_VEBER_RULE>0$$$$

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3D-SDF for NP0002663 (Methyl 4-aminobutyrate)

NP0002663 RDKit 3D 19 18 0 0 0 0 0 0 0 0999 V2000 2.7242 1.0135 -0.1728 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4267 0.4481 -0.2106 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1972 -0.8351 0.1840 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2064 -1.5042 0.5894 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0887 -1.5513 0.1991 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2577 -0.7406 -0.2499 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4922 0.4821 0.6096 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6454 1.2245 0.1160 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4924 0.2798 0.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0122 1.4029 -1.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7546 1.9092 0.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2404 -2.0107 1.1983 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0165 -2.4104 -0.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1262 -0.4910 -1.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1744 -1.3667 -0.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6102 1.1506 0.6597 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7202 0.2000 1.6582 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1236 0.6370 -0.6006 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3511 2.1621 -0.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 1 9 1 0 1 10 1 0 1 11 1 0 5 12 1 0 5 13 1 0 6 14 1 0 6 15 1 0 7 16 1 0 7 17 1 0 8 18 1 0 8 19 1 0M END

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PDB for NP0002663 (Methyl 4-aminobutyrate)

HEADER PROTEIN 04-MAY-14 NONETITLE NULL COMPND NULL SOURCE NULL KEYWDS NULL EXPDTA NULL AUTHOR Marvin REVDAT 1 04-MAY-14 0 HETATM 1 C UNK 0 0.000 0.000 0.000 0.00 0.00 C+0HETATM 2 C UNK 0 0.000 0.000 0.000 0.00 0.00 C+0HETATM 3 C UNK 0 0.000 0.000 0.000 0.00 0.00 C+0HETATM 4 C UNK 0 0.000 0.000 0.000 0.00 0.00 C+0HETATM 5 C UNK 0 0.000 0.000 0.000 0.00 0.00 C+0HETATM 6 N UNK 0 0.000 0.000 0.000 0.00 0.00 N+0HETATM 7 O UNK 0 0.000 0.000 0.000 0.00 0.00 O+0HETATM 8 O UNK 0 0.000 0.000 0.000 0.00 0.00 O+0CONECT 1 8 CONECT 2 3 4 CONECT 3 2 5 CONECT 4 2 6 CONECT 5 3 7 8 CONECT 6 4 CONECT 7 5 CONECT 8 1 5 MASTER 0 0 0 0 0 0 0 0 8 0 14 0END

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3D PDB for NP0002663 (Methyl 4-aminobutyrate)

COMPND NP0002663HETATM 1 C1 UNL 1 2.724 1.014 -0.173 1.00 0.00 C HETATM 2 O1 UNL 1 1.427 0.448 -0.211 1.00 0.00 O HETATM 3 C2 UNL 1 1.197 -0.835 0.184 1.00 0.00 C HETATM 4 O2 UNL 1 2.206 -1.504 0.589 1.00 0.00 O HETATM 5 C3 UNL 1 -0.089 -1.551 0.199 1.00 0.00 C HETATM 6 C4 UNL 1 -1.258 -0.741 -0.250 1.00 0.00 C HETATM 7 C5 UNL 1 -1.492 0.482 0.610 1.00 0.00 C HETATM 8 N1 UNL 1 -2.645 1.225 0.116 1.00 0.00 N HETATM 9 H1 UNL 1 3.492 0.280 0.151 1.00 0.00 H HETATM 10 H2 UNL 1 3.012 1.403 -1.189 1.00 0.00 H HETATM 11 H3 UNL 1 2.755 1.909 0.491 1.00 0.00 H HETATM 12 H4 UNL 1 -0.240 -2.011 1.198 1.00 0.00 H HETATM 13 H5 UNL 1 0.016 -2.410 -0.514 1.00 0.00 H HETATM 14 H6 UNL 1 -1.126 -0.491 -1.308 1.00 0.00 H HETATM 15 H7 UNL 1 -2.174 -1.367 -0.151 1.00 0.00 H HETATM 16 H8 UNL 1 -0.610 1.151 0.660 1.00 0.00 H HETATM 17 H9 UNL 1 -1.720 0.200 1.658 1.00 0.00 H HETATM 18 H10 UNL 1 -3.124 0.637 -0.601 1.00 0.00 H HETATM 19 H11 UNL 1 -2.351 2.162 -0.248 1.00 0.00 H CONECT 1 2 9 10 11CONECT 2 3CONECT 3 4 4 5CONECT 5 6 12 13CONECT 6 7 14 15CONECT 7 8 16 17CONECT 8 18 19END

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SMILES for NP0002663 (Methyl 4-aminobutyrate)

COC(=O)CCCN

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INCHI for NP0002663 (Methyl 4-aminobutyrate)

InChI=1S/C5H11NO2/c1-8-5(7)3-2-4-6/h2-4,6H2,1H3

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Structure for NP0002663 (Methyl 4-aminobutyrate)

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3D Structure for NP0002663 (Methyl 4-aminobutyrate)

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Synonyms

Value	Source
4-Aminobutyric acid methyl ester	ChEBI
Methyl 4-aminobutyrate	ChEBI
Methyl gamma-aminobutyrate	ChEBI
4-Aminobutyrate methyl ester	Generator
Methyl 4-aminobutyric acid	Generator
Methyl g-aminobutyrate	Generator
Methyl g-aminobutyric acid	Generator
Methyl gamma-aminobutyric acid	Generator
Methyl γ-aminobutyrate	Generator
Methyl γ-aminobutyric acid	Generator
Methyl 4-aminobutanoic acid	Generator
GABA methyl ester	MeSH
4-Aminobutyric acid methyl ester hydrochloride	MeSH
gamma-Aminobutyric acid methyl ester	MeSH
Methyl gaba	MeSH

Chemical FormulaC₅H₁₁NO₂Average Mass117.1463 DaMonoisotopic Mass117.07898 DaIUPAC Namemethyl 4-aminobutanoateTraditional Namemethyl 4-aminobutanoateCAS Registry NumberNot AvailableSMILES

COC(=O)CCCN

InChI Identifier

InChI=1S/C5H11NO2/c1-8-5(7)3-2-4-6/h2-4,6H2,1H3

InChI KeyKVQGGLZHHFGHPU-UHFFFAOYSA-NExperimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted SpectraNot AvailableChemical Shift SubmissionsNot AvailableSpeciesSpecies of OriginNot AvailableChemical TaxonomyDescriptionThis compound 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.KingdomOrganic compounds Super ClassOrganic acids and derivatives ClassCarboxylic acids and derivatives Sub ClassAmino acids, peptides, and analogues Direct ParentGamma amino acids and derivatives Alternative Parents

Substituents

Gamma amino acid or derivatives
Fatty acid ester
Fatty acid methyl ester
Fatty acyl
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organic oxide
Aliphatic acyclic compound

Molecular FrameworkAliphatic acyclic compoundsExternal Descriptors

primary amino compound (CHEBI:42955 )
methyl ester (CHEBI:42955 )
amino acid ester (CHEBI:42955 )

Physical PropertiesStateNot AvailableExperimental 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	-0.47	ALOGPS
logP	-0.48	ChemAxon
logS	0.38	ALOGPS
pKa (Strongest Basic)	10.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	30.23 m³·mol⁻¹	ChemAxon
Polarizability	12.73 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External LinksHMDB IDNot AvailableDrugBank IDNot AvailablePhenol Explorer Compound IDNot AvailableFoodDB IDNot AvailableKNApSAcK IDNot AvailableChemspider ID17580 KEGG Compound IDNot AvailableBioCyc IDNot AvailableBiGG IDNot AvailableWikipedia LinkNot AvailableMETLIN IDNot AvailablePubChem CompoundNot AvailablePDB IDNot AvailableChEBI ID42955 Good Scents IDNot AvailableReferencesGeneral References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Frenguelli BG, Blake JF, Brown MW, Collingridge GL: Electrogenic uptake contributes a major component of the depolarizing action of L-glutamate in rat hippocampal slices. Br J Pharmacol. 1991 Feb;102(2):355-62. doi: 10.1111/j.1476-5381.1991.tb12178.x. [PubMed:1673070 ]
Silverman RB, Durkee SC, Invergo BJ: 4-Amino-2-(substituted methyl)-2-butenoic acids: substrates and potent inhibitors of gamma-aminobutyric acid aminotransferase. J Med Chem. 1986 May;29(5):764-70. doi: 10.1021/jm00155a029. [PubMed:3701787 ]