NPs Basic Information

Name
Chlorogenic Acid
Molecular Formula C16H18O9
IUPAC Name*
(1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
SMILES
C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)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
Synonyms
CHLOROGENIC ACID; 327-97-9; 3-O-Caffeoylquinic acid; Heriguard; 3-(3,4-Dihydroxycinnamoyl)quinic acid; 3-Caffeoylquinic acid; Chlorogenate; Hlorogenic acid; CP chlorogenic acid; Chlorogenicacid; NSC-407296; Caffeoyl quinic acid; 5-CQA; (+)-Chlorogenic acid; Chlorogenic acid [MI]; 5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid; trans-Chlorogenic acid; Caffetannic acid; trans-Caffeic acid 5-o-D-quinate; Chlorogenic acid [WHO-DD]; cis-chlorogenic acid; NSC 70861; NSC-70861; NSC 407296; trans-5-O-Caffeoylquinic acid; 318ADP12RI; CHEMBL284616; (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid; 202650-88-2; CHEBI:16112; Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1S-(1-alpha,3-beta,4-alpha,5-alpha))-; Chlorogenic acid (constituent of st. john's wort) [DSC]; MFCD00003862; 3-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid; (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid; Cyclohexanecarboxylic acid, 3-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,4,5-trihydroxy-, (1S,3R,4R,5R)-; Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1S,3R,4R,5R)-; Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1S,3R,4R,5R)-; caffeoylquinic acid; 1,3,4,5-tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate); 3-O-caffeoyl-D-quinic acid; 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate; 3-Caffeoylquinate; 5-Caffeoylquinic acid; 3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy] 1,4,5-trihydroxycyclohexanecarboxylic acid; 5-caffeoyl quinic acid; (1S,3R,4R,5R)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid; [1S-(1alpha,3beta,4alpha,5alpha)]-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid; [1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid; cyclohexanecarboxylic acid, 3-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1S,3R,4R,5R)-; Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, [1S-(1alpha,3beta,4alpha,5alpha)]-; CCRIS 1400; EINECS 206-325-6; 3-trans-Caffeoylquinic acid; UNII-318ADP12RI; Hlorogenate; Helianthic acid; Igasuric acid; NSC70861; Chlorogenic-acid; NSC407296; Caffeylquinic acid; 3-(3,4-Dihydroxycinnamoyl)quinate; Prestwick_112; (E)-chlorogenic acid; Chlorogenic acid, Chiral; Chlorogenic acid (8CI); Prestwick2_000427; Prestwick3_000427; Spectrum5_000733; bmse000387; Quinic acid, 5-caffeoyl-; SCHEMBL19466; BSPBio_000414; BSPBio_003353; SPECTRUM210800; MLS002153805; BIDD:ER0453; BPBio1_000456; Quinic acid, 3-caffeoyl-, E-; ACon1_000581; CHEBI:95271; CHLOROGENIC ACID [USP-RS]; BDBM513080; DTXSID101318952; HMS1569E16; HMS1923C11; HMS2096E16; HMS2235F03; HMS3649E06; ACT03375; ALBB-030169; CGA; HY-N0055; ZINC2138728; BDBM50327036; CCG-38471; s2280; AKOS015955866; AC-6032; Chlorogenic acid, >=95% (titration); CS-3766; DB12029; SDCCGMLS-0066467.P001; NCGC00168941-01; NCGC00168941-02; NCGC00168941-03; (1S,3R,4R,5R)-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid; (1S,3R,4R,5R)-3-[(E)-3-(3,4-DIHYDROXY-PHENYL)-ACRYLOYLOXY]-1,4,5-TRIHYDROXY-CYCLOHEXANECARBOXYLIC ACID; (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylicacid; AS-12284; SMR000857273; Chlorogenic acid 1000 microg/mL in Acetone; Chlorogenic acid 10 microg/mL in Acetonitrile; C00852; F16266; 327C979; Q421964; SR-01000841185; SR-01000946600; D54CAE3D-CDDA-455D-A28E-77FC9EFE4A43; SR-01000841185-4; SR-01000946600-1; BRD-K47114202-001-06-2; 32CF6D13-8F08-485F-B79E-F8A6AC318E07; Chlorogenic acid, primary pharmaceutical reference standard; Chlorogenic acid, European Pharmacopoeia (EP) Reference Standard; Chlorogenic acid, United States Pharmacopeia (USP) Reference Standard; 3-[(E)-3-(3,4-Dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid; 3-[3-(3,4-Dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid; (1R,3S,4S,5S)-3-[(E)-3-(3,4-Dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid; (1S,3R,4R,5R)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylicacid; (1S,3R,4R,5R)-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid; (1S,3R,4R,5R)-3-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic acid; (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexanecarboxylic acid; (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic acid; (1S,3R,4R,5R,E)-3-(3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic acid; CYCLOHEXANECARBOXYLIC ACID, 3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4,5-TRIHYDROXY-, (1S-(1-.ALPHA.,3-.BETA.,4-.ALPHA.,5-.ALPHA.))-; Cyclohexanecarboxylic acid,3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-,(1S,3R,4R,5R)-; edit(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
CAS 202650-88-2
PubChem CID 1794427
ChEMBL ID CHEMBL284616
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Organic oxygen compounds
      • Class: Organooxygen compounds
        • Subclass: Alcohols and polyols
          • Direct Parent: Quinic acids and derivati

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 354.31 ALogp: -0.4
HBD: 6 HBA: 9
Rotatable Bonds: 5 Lipinski's rule of five: Rejected
Polar Surface Area: 165.0 Aromatic Rings: 2
Heavy Atoms: 25 QED Weighted: 0.244

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -6.308 MDCK Permeability: 0.00005500
Pgp-inhibitor: 0 Pgp-substrate: 0.992
Human Intestinal Absorption (HIA): 0.455 20% Bioavailability (F20%): 0.991
30% Bioavailability (F30%): 0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.264 Plasma Protein Binding (PPB): 75.68%
Volume Distribution (VD): 0.554 Fu: 32.92%

ADMET: Metabolism

CYP1A2-inhibitor: 0.057 CYP1A2-substrate: 0.027
CYP2C19-inhibitor: 0.029 CYP2C19-substrate: 0.051
CYP2C9-inhibitor: 0.037 CYP2C9-substrate: 0.485
CYP2D6-inhibitor: 0.003 CYP2D6-substrate: 0.144
CYP3A4-inhibitor: 0.074 CYP3A4-substrate: 0.016

ADMET: Excretion

Clearance (CL): 2.641 Half-life (T1/2): 0.889

ADMET: Toxicity

hERG Blockers: 0.022 Human Hepatotoxicity (H-HT): 0.19
Drug-inuced Liver Injury (DILI): 0.057 AMES Toxicity: 0.033
Rat Oral Acute Toxicity: 0.027 Maximum Recommended Daily Dose: 0.558
Skin Sensitization: 0.149 Carcinogencity: 0.111
Eye Corrosion: 0.004 Eye Irritation: 0.074
Respiratory Toxicity: 0.106
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC001543 1.000 D0KN2M 0.570
ENC001917 0.811 D0V9EN 0.457
ENC001440 0.457 D0I3RO 0.293
ENC001579 0.408 D08HVR 0.284
ENC002582 0.373 D0BA6T 0.277
ENC001101 0.346 D0P7JZ 0.267
ENC004024 0.345 D0U0OT 0.259
ENC002823 0.323 D00KRE 0.245
ENC000002 0.315 D0Y6KO 0.242
ENC000035 0.303 D0E6OC 0.241
*Note: the compound similarity was calculated by RDKIT.