IMPPAT Phytochemical information: 
Arachidonic acid

Arachidonic acid
Summary

SMILES: CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)O
InChI: InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
InChIKey: YZXBAPSDXZZRGB-DOFZRALJSA-N
DeepSMILES: CCCCC/C=CC/C=CC/C=CC/C=CCCCC=O)O
Functional groups: C/C=CC; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Fatty Acyls
ClassyFire Subclass: Fatty acids and conjugates
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Fatty Acids and Conjugates
NP Classifier Class: Unsaturated fatty acids
Synonymous chemical names:
arachidonates, arachidonic acid, arachidonic-acid
External chemical identifiers:
CID:444899; ChEMBL:CHEMBL15594; ChEBI:15843; ZINC:ZINC000004474696; FDASRS:27YG812J1I; SureChEMBL:SCHEMBL16162; MolPort-003-666-529
Chemical structure download


Arachidonic 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


Arachidonic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.31


Arachidonic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.08
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No


Arachidonic acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000155858TRPM5800
ENSP00000215885PLA2G3941
ENSP00000217233TRIB3900
ENSP00000217386OXT844
ENSP00000217964TBL1X900
ENSP00000219070MMP2768
ENSP00000220003CSK700
ENSP00000220584FDFT1900
ENSP00000221307CYP4F3952
ENSP00000221700CYP4F2927
ENSP00000222002SULT2A1900
ENSP00000222381PON1788
ENSP00000222553NAMPT800
ENSP00000222982CYP3A5815
ENSP00000223190NRF1900
ENSP00000225275MPO975
ENSP00000225371EPX711
ENSP00000225728MED31900
ENSP00000227665APOA5900
ENSP00000229135IFNG833
ENSP00000229416GCLC700
ENSP00000236850APOA1980
ENSP00000238651ACOT2800
ENSP00000240055NFYB900
ENSP00000243167FAAH923
ENSP00000243501PLA2G12A916
ENSP00000247992PLA2G2C900
ENSP00000248041CYP4F11833
ENSP00000250971INS724
ENSP00000251535ALOX12992
ENSP00000251871MED17900
ENSP00000252595SLC27A1907
ENSP00000252804PXDN711
ENSP00000252945CYP2E1926
ENSP00000255764MED10900
ENSP00000256104FABP4981
ENSP00000256379MED6900
ENSP00000257215DAGLA900
ENSP00000258648MED4900
ENSP00000258743IL6955
ENSP00000259407BAAT800
ENSP00000260129TGS1900
ENSP00000260302MMP13729
ENSP00000260630CYP1B1919
ENSP00000260682CYP2C9926
ENSP00000260970PPIG910
ENSP00000261488ENOX1800
ENSP00000261523RORA900
ENSP00000261740TRPV4969
ENSP00000262188SMARCD3900
ENSP00000262290LPO711
ENSP00000262367CREBBP900
ENSP00000262735PPARA951
ENSP00000263205MED15900
ENSP00000263253EP300900
ENSP00000263390MED26900
ENSP00000263431PRKCG991
ENSP00000263923KDR815
ENSP00000264110ATF2700
ENSP00000264867PPARGC1A900
ENSP00000265052MGLL919
ENSP00000265350MED20900
ENSP00000265593CLCN2800
ENSP00000265641CPT1A915
ENSP00000265723ABCB4900
ENSP00000266659GLIPR1900
ENSP00000268711MED9900
ENSP00000268712NCOR1900
ENSP00000272190REN873
ENSP00000276414GNRH1786
ENSP00000276914PLIN2917
ENSP00000281455ACSL1929
ENSP00000281928MED13L900
ENSP00000282441YAP1900
ENSP00000282892MED21900
ENSP00000283916TMPRSS11D786
ENSP00000285979CYP2C18818
ENSP00000286317MED7900
ENSP00000287820PPARG951
ENSP00000287936HMGCR924
ENSP00000289473NCF1750
ENSP00000290472PLA2G4D900
ENSP00000290663MED8900
ENSP00000292035MED27900
ENSP00000292596LTC4S937
ENSP00000293761ALOX15987
ENSP00000293777MED11900
ENSP00000295834FABP1960
ENSP00000295897ALB884
ENSP00000296861TNFRSF21900
ENSP00000297056DAGLB900
ENSP00000297347MED30900
ENSP00000300056PEX11A900
ENSP00000300651MED1900
ENSP00000301146CYP2A7800
ENSP00000301455ANGPTL4900
ENSP00000301645CYP7A1900
ENSP00000302150PRL816
ENSP00000302967HDAC3900
ENSP00000303192RGL1900
ENSP00000304811UGT2B7700
ENSP00000304845UGT1A1700
ENSP00000305355PRKCB916
ENSP00000306245FOS952
ENSP00000306497KCNJ4800
ENSP00000306512IL8807
ENSP00000308032CYP2S1800
ENSP00000308165CD36915
ENSP00000308741CLOCK900
ENSP00000309259ALAS1900
ENSP00000310701TEAD2900
ENSP00000311032CASP3808
ENSP00000311095CYP4A11958
ENSP00000311224ACOT1800
ENSP00000312286PLA2G1B997
ENSP00000312649PPARGC1B900
ENSP00000314343MED29900
ENSP00000315167ALOX12B949
ENSP00000318820TPO711
ENSP00000318822BID700
ENSP00000320337PLA2G16900
ENSP00000320940NCOA1900
ENSP00000321106TAC1866
ENSP00000321821CYP4F12931
ENSP00000322229FADS1959
ENSP00000322706HMGCS1900
ENSP00000322909FHL2900
ENSP00000323071ACOT4800
ENSP00000323720MED14900
ENSP00000324648CYP2B6941
ENSP00000324693GRHL1900
ENSP00000325612MED16900
ENSP00000325690CARM1900
ENSP00000326767MED25900
ENSP00000327315TIAM2900
ENSP00000329357SP1907
ENSP00000330237CASP9726
ENSP00000330442PLB1900
ENSP00000332679CYP2A13800
ENSP00000333142PLA2G6963
ENSP00000333212CYP2U1928
ENSP00000333534CYP2F1800
ENSP00000334246CYP4Z1800
ENSP00000334650KCNK18856
ENSP00000337103CHAT800
ENSP00000337340MED19900
ENSP00000337450CYP3A7800
ENSP00000337915CYP3A4731
ENSP00000338018HIF1A900
ENSP00000338185PLCB1900
ENSP00000338283NPAS2900
ENSP00000339787ACSL4946
ENSP00000340820MAPT724
ENSP00000342007CYP1A2911
ENSP00000342343MED22900
ENSP00000343040HMGB1804
ENSP00000343838UGT1A10700
ENSP00000344789ACACA800
ENSP00000345702NFYA900
ENSP00000345772TEAD3900
ENSP00000346103GPX4918
ENSP00000346768UGT1A9900
ENSP00000348645PXDNL711
ENSP00000351273CASP8722
ENSP00000351894NCOA6900
ENSP00000352926TEAD4900
ENSP00000353622SIN3A900
ENSP00000353720CES1700
ENSP00000353820CYP2D6815
ENSP00000353847WWTR1900
ENSP00000354476SREBF2900
ENSP00000354588TEAD1900
ENSP00000354612PTGS1999
ENSP00000354876MT-CO2908
ENSP00000355627AGT915
ENSP00000355759PARP1728
ENSP00000355996G0S2900
ENSP00000356436PLA2G4A985
ENSP00000356438PTGS2999
ENSP00000356954CTGF908
ENSP00000356969APOA2900
ENSP00000357047MED23900
ENSP00000357429FABP7792
ENSP00000357907CDK19909
ENSP00000358414HMGCS2909
ENSP00000358719ME1900
ENSP00000360247CYP2J2975
ENSP00000360266JUN869
ENSP00000360317CYP2C8937
ENSP00000360372CYP2C19912
ENSP00000360541CPT2900
ENSP00000360762ANKRD1900
ENSP00000360958CYP4A22822
ENSP00000360968CYP4X1839
ENSP00000360991CYP4B1923
ENSP00000361066NCOA3900
ENSP00000361405MMP9757
ENSP00000362057NOX1735
ENSP00000362123PLA2G12B900
ENSP00000362508UGT1A4700
ENSP00000362948MED18900
ENSP00000363193MED12900
ENSP00000363512ALOX5999
ENSP00000363868ABCA1911
ENSP00000364035FAAH2900
ENSP00000364243PLA2G2F900
ENSP00000364249PLA2G5927
ENSP00000364252PLA2G2A976
ENSP00000364257PLA2G2E911
ENSP00000367086ACOT7800
ENSP00000368683EDN1837
ENSP00000369050CYP1A1914
ENSP00000369530ALOX15B988
ENSP00000369858ALOX5AP964
ENSP00000370938CDK8909
ENSP00000371833PLA2G4F900
ENSP00000371886JMJD7-PLA2G4B917
ENSP00000374357ARNTL900
ENSP00000376432KCNJ1816
ENSP00000377686MED24900
ENSP00000380888MED13900
ENSP00000382434PLA2G4E900
ENSP00000384018NCOR2900
ENSP00000385806KCNMA1816
ENSP00000393333TBXA2R972
ENSP00000393847PLA2G10964
ENSP00000396045PLA2G4B929
ENSP00000396620NFYC900
ENSP00000398698TNF945
ENSP00000399968NCOA2900
ENSP00000400036PLA2G4C956
ENSP00000400175RHOA844
ENSP00000405574TBL1XR1900
ENSP00000408695PRKCA991
ENSP00000409612ACADM908
ENSP00000417401HELZ2900
ENSP00000418532UGT1A3700
ENSP00000419692RXRA907
ENSP00000428982CCNC900
ENSP00000430269EPHX2929
ENSP00000434516TXNRD1911
ENSP00000451040PGF891
ENSP00000455307CHD9900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.