IMPPAT Phytochemical information: 
Citric acid

Citric acid
Summary

SMILES: OC(=O)C(CC(=O)O)(CC(=O)O)O
InChI: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChIKey: KRKNYBCHXYNGOX-UHFFFAOYSA-N
DeepSMILES: OC=O)CCC=O)O)))CC=O)O)))O
Functional groups: CC(=O)O; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tricarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Fatty Acids and Conjugates
NP Classifier Class: Hydroxy fatty acids
Synonymous chemical names:
citirc acid, citric, citric acid, citric-acid
External chemical identifiers:
CID:311; ChEMBL:CHEMBL1261; ChEBI:30769; ZINC:ZINC000000895081; FDASRS:XF417D3PSL; SureChEMBL:SCHEMBL842; MolPort-046-936-449
Chemical structure download


Citric 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


Citric acid
Drug-likeness
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 2
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4274


Citric acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.69
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


Citric acid
Phytochemical - Predicted human target protein associations
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000003100CYP51A1800
ENSP00000011292CPA1741
ENSP00000198536PILRA800
ENSP00000215754MIF958
ENSP00000215829SNRPD3800
ENSP00000215882SLC25A1900
ENSP00000216194ADSL716
ENSP00000216254ACO2980
ENSP00000216259PMM1739
ENSP00000216780PCK2911
ENSP00000217901IDH3G966
ENSP00000219172CENPT787
ENSP00000222823NOD1800
ENSP00000224181C8G958
ENSP00000225174PPIF800
ENSP00000229447IYD832
ENSP00000232607UMPS739
ENSP00000235835AKR7A2939
ENSP00000247194L3HYPDH715
ENSP00000247970PIN1800
ENSP00000248643MTERF800
ENSP00000248975YWHAH800
ENSP00000250378CMA1800
ENSP00000252603PGLS701
ENSP00000253363RBM39795
ENSP00000253792ACLY985
ENSP00000254878HRSP12771
ENSP00000256078KRAS832
ENSP00000256103PMP2800
ENSP00000256104FABP4800
ENSP00000256759FST800
ENSP00000257868GDF11735
ENSP00000258123USP15800
ENSP00000258418CAB39800
ENSP00000260270FDX1800
ENSP00000260950MSTN795
ENSP00000260985IDH1812
ENSP00000261994SERPINA10800
ENSP00000263549PARP12800
ENSP00000263640ACVR1800
ENSP00000264025PVRL1800
ENSP00000264065DNAJC10794
ENSP00000264193CPOX817
ENSP00000264705CAD737
ENSP00000267953BCL2A1795
ENSP00000268261PMM2739
ENSP00000268695GALNS800
ENSP00000269305TP53845
ENSP00000269321ARHGDIA800
ENSP00000270776PGD783
ENSP00000272102ARF1800
ENSP00000272190REN821
ENSP00000272317RPS27A800
ENSP00000273062CTDSP1958
ENSP00000274353BHMT958
ENSP00000275857NLGN4X800
ENSP00000282957CPB1966
ENSP00000284031DDAH1794
ENSP00000284110HS3ST3A1958
ENSP00000285930AKR1B1967
ENSP00000287878PRKAG2704
ENSP00000287936HMGCR752
ENSP00000287996IPPK752
ENSP00000288014THTPA800
ENSP00000290866ACE729
ENSP00000293636CELA1794
ENSP00000295897ALB865
ENSP00000296161DTX3L800
ENSP00000296581LSM6822
ENSP00000297044CYTH3800
ENSP00000297258FABP5800
ENSP00000297307SLC35G3900
ENSP00000297792KDM1B816
ENSP00000298316ARF6800
ENSP00000299518IDH3A976
ENSP00000299663CLEC4E800
ENSP00000300177GREM1721
ENSP00000302324RNASE3958
ENSP00000304592FASN908
ENSP00000305632HOMER2795
ENSP00000306070NUDT6800
ENSP00000307900GLUL755
ENSP00000308541F2822
ENSP00000309477ACO1976
ENSP00000309968ADAM17800
ENSP00000310244RASGRP1800
ENSP00000311083CKS1B704
ENSP00000312606AKR1A1812
ENSP00000313350RNASEH1800
ENSP00000315693PAM16755
ENSP00000318066ENPP4800
ENSP00000318650GREM2795
ENSP00000318912CA13800
ENSP00000321259TALDO1719
ENSP00000322898EBF1742
ENSP00000323867PRKAG1704
ENSP00000324806GSK3B817
ENSP00000327070MDH2952
ENSP00000327255PPM1A800
ENSP00000327336BGN741
ENSP00000330878KPNA7712
ENSP00000331201HGS953
ENSP00000331897IDH2974
ENSP00000332296RARB800
ENSP00000332455KPNA2742
ENSP00000333203SERPINA5814
ENSP00000334382HOMER1724
ENSP00000336655STRADA800
ENSP00000336762ANG958
ENSP00000337358CECR5755
ENSP00000337733KLK5700
ENSP00000338173PUM2704
ENSP00000339933PKLR835
ENSP00000340925NADK722
ENSP00000342056CS981
ENSP00000342557IL4I1800
ENSP00000342991CLYBL900
ENSP00000343027GNAI1800
ENSP00000343665DOC2B712
ENSP00000344193RNASE1965
ENSP00000344460CBS720
ENSP00000344789ACACA900
ENSP00000345344CTSL800
ENSP00000345512SEMA6A795
ENSP00000346402RNH1800
ENSP00000346437ATG7755
ENSP00000346762SND1814
ENSP00000347046PDE5A958
ENSP00000348068SERPINA1800
ENSP00000348812PTPRD800
ENSP00000348831NUDT10800
ENSP00000349785MAP1LC3C800
ENSP00000350136RIMKLB963
ENSP00000350491PRIM1800
ENSP00000350941SRC825
ENSP00000352516DNMT1795
ENSP00000352956RBM23741
ENSP00000355377AKR7A3704
ENSP00000355518FH713
ENSP00000356150MDM4800
ENSP00000356505NCF2820
ENSP00000356574QSOX1800
ENSP00000356671SERPINC1818
ENSP00000356853UCK2958
ENSP00000356953SDHC720
ENSP00000357097FCER1A800
ENSP00000357153CD1D795
ENSP00000357637EBF3742
ENSP00000357721S100A8800
ENSP00000357726S100A12800
ENSP00000357727S100A9800
ENSP00000357836SNX27800
ENSP00000357986PLEKHA1958
ENSP00000358059RTN4IP1800
ENSP00000358327CASP7800
ENSP00000358765TPBG800
ENSP00000358867GNAI3800
ENSP00000359000GBF1755
ENSP00000359691LGSN701
ENSP00000359991PGAM1800
ENSP00000360181SH2D1A800
ENSP00000360922STAU1800
ENSP00000361850PLAU800
ENSP00000361894GNMT958
ENSP00000362308SH3BGRL800
ENSP00000364694ASPN705
ENSP00000364697PROZ800
ENSP00000364976CKS2704
ENSP00000365048TNFSF13B958
ENSP00000365081APOM800
ENSP00000366620H6PD724
ENSP00000367615APRT948
ENSP00000368523DNAJC15701
ENSP00000369456ITPA936
ENSP00000370129AKR1C2844
ENSP00000370223IDH3B966
ENSP00000370373FKBP1B818
ENSP00000372005DNAJC19755
ENSP00000376544CD79B795
ENSP00000376822STEAP3800
ENSP00000377470CNP701
ENSP00000378326ZP3787
ENSP00000379475DDX39B800
ENSP00000379680NAGA800
ENSP00000382091ALKBH5800
ENSP00000382659TRPV1730
ENSP00000383840MMACHC800
ENSP00000384774HK1825
ENSP00000384957F11800
ENSP00000385021FANCL773
ENSP00000385834TF838
ENSP00000391723PUM1704
ENSP00000392411SLC13A2956
ENSP00000393953PNPT1800
ENSP00000397181RGS4795
ENSP00000398803TSTA3800
ENSP00000405573GPI908
ENSP00000406220SLC13A5956
ENSP00000410294FGFR2800
ENSP00000412566SNRPB800
ENSP00000417281MDM2824
ENSP00000418112PTPRG800
ENSP00000418823FTO800
ENSP00000419851GMPS907
ENSP00000423067WDR36755
ENSP00000435591MUC5AC700
ENSP00000446743938
ENSP00000450399DNM1L800
ENSP00000452780B2M800
ENSP00000460885CORO7-PAM16701
ENSP00000464149729
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.