IMPPAT Phytochemical information: 
Neochlorogenic acid
Neochlorogenic 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-NXLLHMKUSA-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:
neo-chlorogenic-acid, neochlorogenic acid, neochlorogenic, 5-o-caffeoylquinic acid, 5-o-caffeoylquinic-acid, chlorogenic acid, neo, Neochlorogenic acid, neo-chlorogenic acid
External chemical identifiers:
CID:CID_5280633; ChEMBL:CHEMBL249450; ChEBI:CHEBI:16384; ZINC:ZINC000004096248; FDASRS:O4601UER1Z; SureChEMBL:SCHEMBL13567302; MolPort-001-740-201
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Neochlorogenic 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
Neochlorogenic 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 Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.23
Neochlorogenic 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