5-Caffeoylquinic acid (Compound)

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ID	393
Name	5-Caffeoylquinic acid
Synonyms	Chlorogenic acid; 5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid; 3-Caffeoylquinic acid [Old IUPAC, before 1976]; CAS:202650-88-2; KEGG:C00852
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000393 (5-Caffeoylquinic acid) 3D Structure for EE000393 (5-Caffeoylquinic acid) 1794427 -OEChem-09032120363D 43 44 0 1 0 0 0 0 0999 V2000 -1.0078 1.4574 0.1394 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3759 -1.0402 1.2976 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2792 3.1535 -0.4273 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2927 1.5258 0.5209 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2656 -2.5621 -1.7381 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1308 -3.4529 0.1734 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3354 0.4509 2.1073 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6628 -1.7287 0.8328 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3949 -0.0879 -1.2882 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8066 -1.0453 -0.0043 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3597 1.0217 0.2742 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3870 -0.4889 0.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7104 -0.2847 -0.9790 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2445 1.7612 -0.7353 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6808 1.2292 -0.7352 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7664 -2.4871 -0.4808 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1108 0.8730 0.9841 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2015 0.8376 0.2996 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2573 0.2951 0.9228 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6084 0.1919 0.3440 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5023 -0.7279 0.8677 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9585 1.0167 -0.7126 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7814 -0.8255 0.3199 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2376 0.9192 -1.2605 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1489 -0.0019 -0.7442 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6940 1.2592 1.2926 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8614 -0.6920 -0.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8157 -1.0235 0.7898 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7430 -0.6412 -0.8683 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4156 -0.4587 -2.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8159 1.6690 -1.7410 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2678 1.7504 -1.5000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7567 -1.4850 1.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3595 3.4687 -0.4053 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2037 1.1873 0.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2302 -3.4866 -2.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2417 1.2402 -0.7058 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1472 -0.1181 1.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2241 -1.3748 1.6962 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2902 1.7621 -1.1317 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5199 1.5666 -2.0864 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5702 -1.4590 0.6175 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7786 -0.9577 -1.0915 H 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 1 17 1 0 0 0 0 2 10 1 0 0 0 0 2 33 1 0 0 0 0 3 14 1 0 0 0 0 3 34 1 0 0 0 0 4 15 1 0 0 0 0 4 35 1 0 0 0 0 5 16 1 0 0 0 0 5 36 1 0 0 0 0 6 16 2 0 0 0 0 7 17 2 0 0 0 0 8 23 1 0 0 0 0 8 42 1 0 0 0 0 9 25 1 0 0 0 0 9 43 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 12 28 1 0 0 0 0 13 15 1 0 0 0 0 13 29 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 18 37 1 0 0 0 0 19 20 1 0 0 0 0 19 38 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 21 39 1 0 0 0 0 22 24 2 0 0 0 0 22 40 1 0 0 0 0 23 25 2 0 0 0 0 24 25 1 0 0 0 0 24 41 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 1794427 > <PUBCHEM_CONFORMER_RMSD> 0.8 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 21 63 106 119 102 96 146 130 69 112 100 35 135 66 121 93 24 17 54 110 95 92 82 84 72 10 80 125 76 86 137 67 124 39 75 26 132 142 158 128 74 107 23 94 50 18 79 65 141 133 16 44 115 83 68 56 87 134 62 123 30 111 156 53 81 99 37 25 113 77 89 33 136 5 20 31 149 155 157 114 108 4 138 57 47 131 55 70 41 101 49 73 126 13 64 52 129 46 104 98 38 61 6 154 36 103 144 97 14 147 109 85 58 150 127 140 8 117 22 51 12 145 3 42 88 159 19 60 78 32 148 152 2 105 11 139 45 90 9 34 15 143 59 48 120 28 151 29 122 118 7 27 153 71 91 43 116 40 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 34 1 -0.43 10 0.34 11 0.28 14 0.28 15 0.28 16 0.66 17 0.71 18 -0.14 19 -0.18 2 -0.68 20 0.03 21 -0.15 22 -0.15 23 0.08 24 -0.15 25 0.08 3 -0.68 33 0.4 34 0.4 35 0.4 36 0.5 37 0.15 38 0.15 39 0.15 4 -0.68 40 0.15 41 0.15 42 0.45 43 0.45 5 -0.65 6 -0.57 7 -0.57 8 -0.53 9 -0.53 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 6.2 > <PUBCHEM_PHARMACOPHORE_FEATURES> 14 1 2 acceptor 1 2 donor 1 3 acceptor 1 3 donor 1 4 acceptor 1 4 donor 1 5 acceptor 1 6 acceptor 1 7 acceptor 1 8 donor 1 9 donor 3 5 6 16 anion 6 10 11 12 13 14 15 rings 6 20 21 22 23 24 25 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 25 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 4 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 1 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 10 > <PUBCHEM_CONFORMER_ID> 001B617B00000001 > <PUBCHEM_MMFF94_ENERGY> 69.5883 > <PUBCHEM_FEATURE_SELFOVERLAP> 71.134 > <PUBCHEM_SHAPE_FINGERPRINT> 10595046 47 18260269676847310276 10803635 8 18341327825324139431 11135609 149 15793395364637434674 11135609 99 18058163935447945374 11315181 36 16630525141765043737 11524674 6 17203326711055562239 11796584 16 18272088275646882718 12236239 1 17894632530595310452 12616971 3 17894911815333697088 12969540 114 15140673700589332536 13167823 11 18260546714900926680 13690498 29 18335980969346031135 14251751 18 18343578573197988810 14251752 14 18335981991574504242 14251757 5 18336549437953132858 14528608 73 17894633665078456892 15183329 4 18187364311988625508 15250474 111 18187912959501238714 16990350 14 16687958921869602760 16992828 155 17243011250766920165 17780758 139 17346606300179847931 17844677 252 18343864433183925704 17870717 6 18343301466134465861 18927931 339 18411983580986946359 20281389 69 11818994089439417596 21033648 144 15936980755268983166 21307412 95 18197203958064547143 21623969 137 16415483761859342068 220451 1 18335707113699293376 22393880 68 18410569604749091504 23081809 10 17676206849915674136 23198884 109 17240484693103692497 23402539 116 17749108876856567884 23559900 14 18270387390819283672 25122255 55 17917721171452033822 2838139 119 16515402984893114388 3004659 81 18333729084023260218 314173 85 16343704322435308352 4015057 19 17313677052499837044 44062 13 18342172288956501799 484985 159 17917719028448294179 497634 4 16660364801122216675 531348 171 18262516992066090635 559249 180 18412257312137531015 59755656 520 16298673806429084089 6437827 68 18341047437191127598 7495541 125 18272930553357325456 7970288 3 17833548273484051355 > <PUBCHEM_SHAPE_MULTIPOLES> 461.66 17.58 2.56 1.31 23.55 1.17 -0.07 4.25 4.19 -4.8 0.47 0.3 0.12 -1 > <PUBCHEM_SHAPE_SELFOVERLAP> 981.935 > <PUBCHEM_SHAPE_VOLUME> 254.1 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description	There is a confusion between two IUPAC nomenclatures. 5-CQA and 3-CQA should respectively correspond to chlorogenic acid and neochlorogenic acid. However many databases and publications still use the former nomenclature.
Classification	Compounds > Chemical entities > Organic compounds > Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclic alcohols and derivatives > Cyclitols and derivatives > Quinic acids and derivatives
CAS number	327-97-9
PubChem ID	1794427
ChEBI ID	16112
FooDB ID	FDB002582
HMDB ID	HMDB0003164

Chemical data

MolDBi data

IUPAC Name	(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Traditional IUPAC Name	chlorogenic acid
Formula	C16H18O9
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
InChI Key	CWVRJTMFETXNAD-JUHZACGLSA-N
Molecular weight	354.3087
Exact mass	354.095082174
SMILES	O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Alcohols and polyols
Direct Parent	Quinic acids and derivatives
Alternative Parents	Coumaric acids and derivatives Cinnamic acid esters Styrenes Catechols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Fatty acid esters Cyclohexanols Alpha hydroxy acids and derivatives Dicarboxylic acids and derivatives Tertiary alcohols Enoate esters Polyols Carboxylic acids Hydrocarbon derivatives Carbonyl compounds Organic oxides

Publications with 5-Caffeoylquinic acid

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of 5-Caffeoylquinic acid in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of 5-Caffeoylquinic acid with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of 5-Caffeoylquinic acid with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of 5-Caffeoylquinic acid exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of 5-Caffeoylquinic acid exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication