IMPPAT Phytochemical information: 
gamma-Aminobutyric acid

gamma-Aminobutyric acid
Summary

SMILES: NCCCC(=O)O
InChI: InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
InChIKey: BTCSSZJGUNDROE-UHFFFAOYSA-N
DeepSMILES: NCCCC=O)O
Functional groups: CC(=O)O; CN
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Amino acids and Peptides
NP Classifier Superclass: Small peptides
NP Classifier Class: Aminoacids
Synonymous chemical names:
butyric acid, 4-amino, butyric acid, gamma-amino, gaba, gamma-aminobutyric acid, gamma-butyric acid, γ-aminobutyric acid
External chemical identifiers:
CID:119; ChEMBL:CHEMBL96; ChEBI:59888; ZINC:ZINC000001532620; FDASRS:2ACZ6IPC6I; SureChEMBL:SCHEMBL4878; MolPort-000-146-216
Chemical structure download


gamma-Aminobutyric acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit


gamma-Aminobutyric acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.52


gamma-Aminobutyric acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -9.18
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


gamma-Aminobutyric acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000014930HEBP1900
ENSP00000023897GABRA1995
ENSP00000176183DRD4914
ENSP00000216629BDKRB1900
ENSP00000217305PDYN934
ENSP00000217420SLC32A1944
ENSP00000222256RAB3A900
ENSP00000223642C5900
ENSP00000225992PPY917
ENSP00000226317CXCL6900
ENSP00000227378HSPA8900
ENSP00000229264GNB3900
ENSP00000231188GRM6900
ENSP00000231751LTF741
ENSP00000234961OPRD1900
ENSP00000240615TAS2R8900
ENSP00000240619TAS2R10900
ENSP00000240687TAS2R7900
ENSP00000240691TAS2R9900
ENSP00000242152NPY954
ENSP00000245907C3900
ENSP00000246115S1PR4900
ENSP00000246657CCR7900
ENSP00000247879TAS2R3900
ENSP00000247881TAS2R4900
ENSP00000247883TAS2R5900
ENSP00000248572GNGT1900
ENSP00000249016MCHR1900
ENSP00000249041GALR3900
ENSP00000249284TAS2R16900
ENSP00000254235ADCY7900
ENSP00000254488SLC6A11973
ENSP00000254976SNAP25911
ENSP00000255008SSTR4909
ENSP00000255262NMUR2909
ENSP00000256906HRH4900
ENSP00000257068MTNR1B900
ENSP00000257254APLNR900
ENSP00000257497ANXA1900
ENSP00000259271GAD2997
ENSP00000259455GABBR2996
ENSP00000259607CCL21912
ENSP00000259631CCL27900
ENSP00000260600ADCY3900
ENSP00000261205SYT1908
ENSP00000264218NMU900
ENSP00000264318GABRA4972
ENSP00000264708POMC938
ENSP00000265023KNG1909
ENSP00000265294GABRP951
ENSP00000265572OPRK1934
ENSP00000265643GAL930
ENSP00000267377SSTR1907
ENSP00000268251ABAT997
ENSP00000272644GPR17900
ENSP00000272928ACKR3900
ENSP00000274545GABRA6971
ENSP00000274547GABRB2980
ENSP00000280155ADRA2A900
ENSP00000281806MCHR2900
ENSP00000284981APP909
ENSP00000286355ADCY8900
ENSP00000286758CXCL13900
ENSP00000287641SST942
ENSP00000287766SLC6A1980
ENSP00000287907HTR5A900
ENSP00000292174CXCR5900
ENSP00000292301CCR2900
ENSP00000292303CCR5900
ENSP00000293272CCL5900
ENSP00000293275CCL16900
ENSP00000293778CXCL16900
ENSP00000293897SSTR5912
ENSP00000294016ADCY9900
ENSP00000294117GNG3900
ENSP00000295452GABRG1958
ENSP00000295454GABRB1983
ENSP00000295683CXCR1900
ENSP00000296026CXCL3900
ENSP00000296027CXCL5900
ENSP00000296028PPBP900
ENSP00000296140CCR1900
ENSP00000297313RGS20900
ENSP00000297323ADCY1900
ENSP00000297469GPER1917
ENSP00000298440OXGR1900
ENSP00000299267GABRB3975
ENSP00000299727GALR1900
ENSP00000300406GNGT2900
ENSP00000300873GNG8900
ENSP00000301908PNOC917
ENSP00000302079C3AR1900
ENSP00000302150PRL826
ENSP00000302707FPR1900
ENSP00000302811MTNR1A900
ENSP00000304414CXCR6900
ENSP00000305260GNB2900
ENSP00000305416S1PR1900
ENSP00000305464APLN900
ENSP00000305613CPLX1900
ENSP00000305651CXCL10900
ENSP00000305877NMUR1900
ENSP00000306512IL8900
ENSP00000306884CXCL11908
ENSP00000307259P2RY12900
ENSP00000307713BDKRB2900
ENSP00000307766HTR1E900
ENSP00000308361P2RY14900
ENSP00000308549ADORA1912
ENSP00000308815CCL19911
ENSP00000311405ADCY6900
ENSP00000312126ADCY4900
ENSP00000312999GNAI2913
ENSP00000313661HTR1D900
ENSP00000314214VAMP2908
ENSP00000314649ALDH5A1728
ENSP00000316244HTR1A934
ENSP00000319635CXCR2900
ENSP00000319984CHRM2908
ENSP00000320376P2RY13900
ENSP00000322924HTR1F911
ENSP00000324248PENK915
ENSP00000324553GPR156800
ENSP00000325548CNDP2907
ENSP00000326432CCR8900
ENSP00000327724TAS2R60900
ENSP00000327875LPAR5900
ENSP00000328472S1PR5900
ENSP00000328708RXFP3900
ENSP00000329684GALR2900
ENSP00000330070NPW900
ENSP00000330138SSTR3900
ENSP00000330284NPBWR1900
ENSP00000331912GABRG3965
ENSP00000331983LRRC16A795
ENSP00000332225PMCH907
ENSP00000332504CCR10900
ENSP00000332591NPY2R900
ENSP00000332659CCR4900
ENSP00000332766NPB900
ENSP00000332812PTGDR2900
ENSP00000333194RGS19900
ENSP00000334050TAS2R42900
ENSP00000334448GNG2900
ENSP00000334958RLTPR701
ENSP00000335592GABRA5981
ENSP00000336764OPRL1907
ENSP00000339260SLC6A13965
ENSP00000339377NPY5R900
ENSP00000339393CCR6900
ENSP00000340191FPR2900
ENSP00000341821FPR3900
ENSP00000342560HRH3900
ENSP00000342952ADCY2919
ENSP00000343027GNAI1913
ENSP00000343428GPR18900
ENSP00000344173GRM8911
ENSP00000345774ALDH3A2932
ENSP00000346827ALDH9A1921
ENSP00000347197C5AR1900
ENSP00000348897GABRA2986
ENSP00000348918SAA1900
ENSP00000349003PTGER3900
ENSP00000349478HCAR1900
ENSP00000350198SSTR2900
ENSP00000350256CCR9900
ENSP00000350348GRM7923
ENSP00000350878S1PR3900
ENSP00000350928GAD1999
ENSP00000351671CCL20900
ENSP00000351682CNDP1922
ENSP00000351755LPAR1900
ENSP00000352702SLC6A12954
ENSP00000353198PYY909
ENSP00000354111DNAJC5900
ENSP00000354416CCL28900
ENSP00000354652NPY1R907
ENSP00000354859DRD2937
ENSP00000354901CXCL9900
ENSP00000355156SUCNR1900
ENSP00000355316GRM3924
ENSP00000355523RGS7900
ENSP00000355556GNG4900
ENSP00000355627AGT909
ENSP00000356429RGS1900
ENSP00000356430RGS18900
ENSP00000357301RXFP4900
ENSP00000358099RGS10900
ENSP00000358511CNR1936
ENSP00000358730ADORA3900
ENSP00000358783NPBWR2900
ENSP00000358867GNAI3913
ENSP00000358963HTR1B912
ENSP00000359329GABRQ874
ENSP00000359334968
ENSP00000359353GABRE961
ENSP00000359643LPAR3900
ENSP00000359675GNG5900
ENSP00000360021GNG12900
ENSP00000360973AGTR2900
ENSP00000362014DNM1907
ENSP00000362795CXCR3900
ENSP00000363296GRM4911
ENSP00000363411GNG10900
ENSP00000363431NPY4R900
ENSP00000363596CNR2900
ENSP00000363643P2RY4900
ENSP00000365576UBQLN1900
ENSP00000366061NMS900
ENSP00000366233GABBR1973
ENSP00000366927ALDH1B1909
ENSP00000367848GABRD952
ENSP00000367869909
ENSP00000367930OXER1900
ENSP00000367959HTR2A722
ENSP00000370571TH711
ENSP00000371594GNG7900
ENSP00000371932TAS2R1900
ENSP00000373169DRD3923
ENSP00000375066HCAR2900
ENSP00000375086CCL25900
ENSP00000375091TAS2R19900
ENSP00000375093TAS2R31900
ENSP00000375095TAS2R13900
ENSP00000375893GPR55900
ENSP00000378492GRM2931
ENSP00000379110CXCL1900
ENSP00000379140CXCL12908
ENSP00000379895GATM979
ENSP00000380227ITGA4800
ENSP00000381339GNAT3913
ENSP00000384665LPAR2900
ENSP00000385834TF763
ENSP00000386029GABRR2973
ENSP00000386069ADRA2C900
ENSP00000386201TAS2R41900
ENSP00000386210TAS2R40900
ENSP00000386229RGS14907
ENSP00000386884CXCR4900
ENSP00000387123ALDH7A1913
ENSP00000387281ADRA2B908
ENSP00000389009CARNS1920
ENSP00000394624OPRM1953
ENSP00000397181RGS4909
ENSP00000405095TAS2R39900
ENSP00000409378CHRM4900
ENSP00000410732GABRG2981
ENSP00000412673GABRR1971
ENSP00000417901GPHN950
ENSP00000419361ADCY5900
ENSP00000420194CASR909
ENSP00000424040TAS2R50900
ENSP00000427279CXCL2900
ENSP00000428417RIMS1900
ENSP00000431719TAS2R43900
ENSP00000436450TAS2R46900
ENSP00000436714HCAR3900
ENSP00000441600CCR3900
ENSP00000441624TAS2R20900
ENSP00000441949TAS2R14900
ENSP00000444736TAS2R30900
ENSP00000448219TAS2R38910
ENSP00000450353900
ENSP00000451030RGS6900
ENSP00000466933S1PR2900
ENSP00000468991MTRNR2L12900
ENSP00000471569967
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.