IMPPAT Phytochemical information: 
Chlorogenic acid
Chlorogenic acid
Summary

SMILES: O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI: InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
InChIKey: CWVRJTMFETXNAD-JUHZACGLSA-N
DeepSMILES: O=CO[C@@H]C[C@@]O)C[C@H][C@H]6O))O)))C=O)O))))))/C=C/cccccc6)O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCCCC1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCCCC1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCCCC1
Functional groups: c/C=C/C(=O)OC; CO; CC(=O)O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Alcohols and polyols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
chlorogenic acid, 3-caffeoylquinic-acid, caffeoylquinic acid, 3-o-caffeoylquinic acid, chlorogenic-acid, caffeoyl quinic acid, acid chlorogenic, 3-mono-o-caffeoylquinic acid (chlorogenic acid), chlorogenic scid, Caffeoyl quinic acid, 3-caffeoylquinic acid
External chemical identifiers:
CID:CID_1794427; ChEMBL:CHEMBL284616; ChEBI:CHEBI:16112; ZINC:ZINC000002138728; FDASRS:318ADP12RI; SureChEMBL:SCHEMBL19466; MolPort-001-740-212
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Chlorogenic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.31
Log P RDKit -0.65
Topological polar surface area (Å2) RDKit 164.75
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Chlorogenic acid
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.234085
Chlorogenic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.76
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
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
Chlorogenic acid
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001316ENSG00000179295PTPN115781ChEMBL, NPASS
TAR_EXP_001554ENSG00000291971SRC6714ChEMBL, NPASS
TAR_EXP_001567ENSG00000115415STAT16772ChEMBL, NPASS
TAR_EXP_001726ENSG00000163517HDAC1179885ChEMBL
TAR_EXP_001569ENSG00000173757STAT5B6777ChEMBL, NPASS
TAR_EXP_001928ENSG00000068024HDAC49759ChEMBL
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_001831ENSG00000171720HDAC38841ChEMBL
TAR_EXP_001761ENSG00000100429HDAC1083933ChEMBL, NPASS
TAR_EXP_001568ENSG00000168610STAT36774ChEMBL, NPASS
TAR_EXP_001926ENSG00000048052HDAC99734ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000684ENSG00000116478HDAC13065BindingDB, ChEMBL
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL, NPASS
TAR_EXP_001308ENSG00000175354PTPN25771BindingDB, ChEMBL, NPASS
TAR_EXP_001222ENSG00000147099HDAC855869ChEMBL
TAR_EXP_001165ENSG00000241119UGT1A954600ChEMBL, NPASS
TAR_EXP_001163ENSG00000167165UGT1A654578ChEMBL, NPASS
TAR_EXP_001075ENSG00000061273HDAC751564ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL, NPASS
TAR_EXP_000752ENSG00000142192APP351BindingDB, ChEMBL, NPASS
TAR_EXP_000685ENSG00000196591HDAC23066ChEMBL
TAR_EXP_001311ENSG00000111679PTPN65777ChEMBL, NPASS
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000005ENSG00000108840HDAC510014ChEMBL
TAR_EXP_000053ENSG00000079337RAPGEF310411NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000102ENSG00000091428RAPGEF411069NPASS
TAR_EXP_000329ENSG00000108861DUSP31845ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000518ENSG00000281500SLC37A42542NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS