Chlorogenic acid






Names

    • DTXCID604786
    • Chlorogenic acid,
    • F16266
    • Chlorogenic acid [WHO-DD]
    • BPBio1_000456
    • Chlorogenic acid [MI]
    • AKOS015955866
    • NSC-70861
    • 327-97-9
    • CHEBI:16112
    • Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1S-(1alpha,3beta,4alpha,5alpha))-
    • Chlorogenic acid, primary pharmaceutical reference standard
    • CHEMBL284616
    • Chlorogenic Acid1510
    • CHLOROGENIC ACID
    • NSC 407296
    • 5-CQA
    • 32CF6D13-8F08-485F-B79E-F8A6AC318E07
    • 3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy] 1,4,5-trihydroxycyclohexanecarboxylic acid
    • 3 Caffeoylquinic Acid
    • NSC70861
    • Chlorogenic acid, United States Pharmacopeia (USP) Reference Standard
    • HMS1569E16
    • Chlorogenic acid (Standard)
    • MLS002153805
    • EINECS 206-325-6
    • Prestwick3_000427
    • Hlorogenic acid
    • Heriguard
    • HY-N0055R
    • 3-trans-Caffeoylquinic acid
    • ACon1_000581
    • (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-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
    • Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1S,3R,4R,5R)-
    • Chlorogenic acid
    • NCGC00168941-05
    • DB12029
    • DTXSID101318952
    • HMS2235F03
    • 318ADP12RI
    • SCHEMBL19466
    • 5-caffeoyl quinic acid
    • NCGC00168941-01
    • SMR000857273
    • trans-Caffeic acid 5-o-D-quinate
    • (1S,3R,4R,5R,E)-3-(3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic acid
    • SR-01000946600
    • Prestwick2_000427
    • GTPL12477
    • NS00015066
    • Chlorogenate
    • Quinic acid, 5-caffeoyl-
    • BRD-K47114202-001-14-6
    • NSC-407296
    • trans-Chlorogenic acid
    • 3-O-Caffeoylquinic acid
    • trans-5-O-Caffeoylquinic acid
    • C00852
    • Tox21_202495
    • (1S,3R,4R,5R)-3-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic acid
    • CHLOROGENIC ACID (USP-RS)
    • HY-N0055
    • DTXSID3024786
    • [1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
    • Chlorogenic-acid
    • edit(1S,3R,4R,5R)-3-(((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic 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))-
    • HMS3649E06
    • 5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid
    • BDBM50327036
    • Caffeoyl quinic acid
    • BRD-K47114202-001-06-2
    • (1S,3R,4R,5R)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid
    • CCG-38471
    • BSPBio_003353
    • 1ST40089
    • Acid, Chlorogenic
    • CAS-327-97-9
    • cyclohexanecarboxylic acid, 3-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1S,3R,4R,5R)-
    • 3-O-caffeoyl-D-quinic acid
    • CHLOROGENIC ACID [USP-RS]
    • 1,3,4,5-tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate)
    • 3-Caffeoylquinate
    • CS-3766
    • NSC 70861
    • Cyclohexanecarboxylic acid, 3-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,4,5-trihydroxy-, (1S,3R,4R,5R)-
    • CCRIS 1400
    • SR-01000841185
    • 3-(3,4-Dihydroxycinnamoyl)quinic acid
    • bmse000387
    • SDCCGMLS-0066467.P001
    • (1S,3R,4R,5R)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylicacid
    • AC-6032
    • Chlorogenicacid
    • CP chlorogenic acid
    • AS-12284
    • SPECTRUM210800
    • Chlorogenic acid hemihydrate
    • BSPBio_000414
    • D54CAE3D-CDDA-455D-A28E-77FC9EFE4A43
    • edit(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
    • ALBB-030169
    • UNII-318ADP12RI
    • 3-Caffeoylquinic acid
    • (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
    • (+)-Chlorogenic acid
    • 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate
    • Chlorogenic acid (8CI)
    • Chlorogenic acid (constituent of echinacea angustifolia root, echinacea pallida root, echinacea purpurea root and echinacea purpurea aerial parts)
    • 5-O-Caffeoylquinic acid
    • (1S-(1alpha,3beta,4alpha,5alpha))3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid
    • s2280
    • (1S,3R,4R,5R)-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid
    • NSC407296
    • Chlorogenic acid, European Pharmacopoeia (EP) Reference Standard
    • NCGC00168941-03
    • HMS2096E16
    • Chlorogenic acid, >=95% (titration)
    • AP-163/40806917', "Chlorogenic acid (constituent of st. john's wort)", 'Q421964
    • SR-01000841185-4
    • 3-[(E)-3-(3,4-Dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
    • BIDD:ER0453
    • Acid, 3-Caffeoylquinic
    • 202650-88-2
    • SR-01000946600-1
    • 3-(3,4-Dihydroxycinnamoyl)quinate
    • 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.))-
    • (1S,3R,4R,5R)-3-[(E)-3-(3,4-DIHYDROXY-PHENYL)-ACRYLOYLOXY]-1,4,5-TRIHYDROXY-CYCLOHEXANECARBOXYLIC ACID
    • Chlorogenic acid 10 microg/mL in Acetonitrile
    • Hlorogenate
    • MFCD00003862
    • HMS1923C11
    • [1S-(1alpha,3beta,4alpha,5alpha)]-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
    • Chlorogenic acid 1000 microg/mL in Acetone
    • Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1S,3R,4R,5R)-', "Chlorogenic acid (constituent of st. john's wort) [DSC]", '3-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid
    • Cyclohexanecarboxylic acid,3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-,(1S,3R,4R,5R)-
    • Chlorogenic acid, Chiral
    • (E)-chlorogenic acid
    • Spectrum5_000733
    • NCGC00168941-02
    • (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylicacid
    • BDBM513080
    • 3-[3-(3,4-Dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid', "cyclohexanecarboxylic acid, 3-(3',4'-dihydroxycinnamoyl)oxy-1,4,5-trihydroxy-", '(1R,3S,4S,5S)-3-[(E)-3-(3,4-Dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
    • CHEBI:95271
    • NCGC00260044-01
    • Prestwick_112
    • (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
    • Quinic acid, 3-caffeoyl-, E-
    • Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, [1S-(1alpha,3beta,4alpha,5alpha)]-

Attributes

  • Canonical 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

  • Molecule Class: Minor compounds
  • TPSA: 164.75
  • #RotBonds: 4
  • MW: 354.31100000000004
  • HBD: 6
  • HBA: 8
  • logP: -0.6459000000000001
  • Chemical Formula: C16H18O9


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • HPLC analysis and antimicrobial, antimycobacterial and antiviral activities of Tabernaemontana catharinensis A. DC Journal of Applied Biomedicine, 2015 (DOI).

Compound-Protein Relationships


Compound Activities

    • Antimicrobial
    • Antiherpetic
    • Antiviral
    • Cytotoxicity
    • Antiherpes
    • Antimycobacterial

Predicted NMR Spectral Data


Predicted MS Fragmentation Patternn


Predicted ADMET Properties

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -6.49
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.13
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.61
    Distribution Blood-Brain Barrier (Central Nervous System) -3.6
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.64
    Plasma Protein Binding 62.75
    Steady State Volume of Distribution 0.47
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.32
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -2.33
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.63
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 4.17
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -0.41
    Rat (Acute) 1.88
    Rat (Chronic Oral) 3.28
    Fathead Minnow 3.87
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 456.41
    Hydration Free Energy -9.41
    Log(D) at pH=7.4 -1.0
    Log(P) -0.64
    Log S -1.34
    Log(Vapor Pressure) -13.66
    Melting Point 201.67
    pKa Acid 3.22
    pKa Basic 7.01