4-Caffeoylquinic acid (Compound)

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ID	2364
Name	4-Caffeoylquinic acid
Synonyms	Cryptochlorogenic acid; CAS:87099-73-8
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE002364 (4-Caffeoylquinic acid) 3D Structure for EE002364 (4-Caffeoylquinic acid) 9798666 -OEChem-12292200443D 43 44 0 1 0 0 0 0 0999 V2000 -0.6452 0.5143 0.2907 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7563 0.1915 -1.8134 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4525 2.6339 0.9302 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1392 -0.9493 -1.5329 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4483 -0.3859 1.2421 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1611 -0.2869 -0.9208 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1041 -1.5358 1.2080 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1194 2.2854 -0.4600 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9672 0.2158 -0.6259 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8181 0.0237 -0.4022 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0274 0.2860 0.5601 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3284 1.2905 0.3024 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9970 -1.2093 0.0024 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8256 1.5167 0.1235 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4868 -0.9926 -0.1484 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2651 -0.2299 -0.0919 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2014 -0.4837 0.6695 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5773 -0.0686 0.3134 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6038 -0.8904 0.5747 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0127 -0.5959 0.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4006 0.7171 0.0475 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9218 -1.6384 0.1795 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7343 0.9953 -0.2519 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2553 -1.3602 -0.1200 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6616 -0.0434 -0.3357 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1416 0.1717 1.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8643 2.1710 -0.0772 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5535 1.2568 1.3770 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2007 -1.4820 1.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2954 -2.0607 -0.6237 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5870 1.7804 -0.9133 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0162 -1.8955 0.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2075 1.0222 -2.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9614 3.4026 0.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6325 -0.2244 -1.9512 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3889 -0.5516 1.4659 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6891 0.8926 -0.1746 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4243 -1.8559 1.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7132 1.5540 0.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6202 -2.6696 0.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9673 -2.1788 -0.1823 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0727 2.2924 -0.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4606 -0.6223 -0.6415 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 14 1 0 0 0 0 11 15 1 0 0 0 0 11 26 1 0 0 0 0 12 14 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 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> 9798666 > <PUBCHEM_CONFORMER_RMSD> 0.8 > <PUBCHEM_CONFORMER_DIVERSEORDER> 2 126 39 120 115 111 97 36 92 43 68 7 79 56 71 102 87 80 45 124 50 101 121 16 28 11 78 118 67 91 55 60 46 18 94 75 72 130 73 74 96 105 37 8 30 62 20 1 53 110 59 84 95 47 63 22 6 76 58 32 40 69 48 5 52 33 29 10 103 77 34 117 66 38 61 27 116 51 25 23 106 85 31 107 125 3 88 65 128 15 81 83 26 100 42 41 108 129 57 44 64 21 9 113 89 54 82 13 49 12 90 14 35 24 19 114 70 104 112 127 123 86 109 93 99 119 17 122 4 98 > <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> 2 > <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> 0095840A00000002 > <PUBCHEM_MMFF94_ENERGY> 66.5631 > <PUBCHEM_FEATURE_SELFOVERLAP> 71.126 > <PUBCHEM_SHAPE_FINGERPRINT> 10 15 14345799370713498774 10299344 5 17917994975263595451 10595046 47 18412826850644507722 10730089 173 18342458127477677329 10968037 39 18410011040168334299 11101153 10 18408608062746606693 11315181 36 18113903758467682433 11524674 6 14979952588636553405 12107183 9 17546728158380142682 12166972 35 18113622291554016100 12236239 1 18409166584519212601 12516196 113 17275381002115770680 12616971 3 12175606383224356226 13288520 33 18059852862247497505 13533116 47 18336261254902098794 13685833 64 12895353304737128494 13885169 127 13758085073211890243 14123256 10 18411699889785803744 14251764 18 18408886218440604042 14528608 73 18408886239873281306 14856354 85 16917068876175921333 14933364 13 18334014990683572514 15183329 4 18413108351391210466 15461852 350 14707219828503985930 1577012 14 18337392630538543080 15849732 13 17894914039937047679 17844677 252 18339649953833054080 18335252 98 18187372047114567011 20157964 124 18408605864619318410 20281389 69 17313098653416475094 20554085 129 15068612807774460921 21033648 29 16443337681235701436 21150785 3 18334576849842011630 21236236 1 18272653398933078857 21267235 1 18342457067480403459 21315763 28 18410573955714635458 220451 1 17489586749016164766 221357 26 18343580742235932560 22224240 67 12251903720185504416 2297311 6 17847059969786578305 23035841 295 17489586762101188699 23198884 109 18407759222810887075 23522609 53 17773620323776588257 23559900 14 18340761666951468817 23569943 247 17316475103476477906 29717793 49 18060706079054864334 3004659 81 18343582907353032650 335352 9 18343575241184380757 34797466 226 17560807649829886996 3545911 37 18260267455805730314 4073 2 17967820500518619666 4258327 124 16733849604144837334 4325135 7 18413671314208259350 497634 4 18409729517483149741 54039377 194 18058440076291487751 542803 24 18410009927676859186 54446538 1 18410292489280380152 59755656 520 17458622341420745051 > <PUBCHEM_SHAPE_MULTIPOLES> 461.66 21.22 1.71 1.01 12.46 0.76 -0.18 0.87 -4.26 0.88 0.22 -1.09 -0.08 -0.76 > <PUBCHEM_SHAPE_SELFOVERLAP> 982.747 > <PUBCHEM_SHAPE_VOLUME> 253.5 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description
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	905-99-7
PubChem ID	9798666
ChEBI ID	75491
FooDB ID	FDB002561
HMDB ID	HMDB0030653

Chemical data

MolDBi data

IUPAC Name	(3R,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexane-1-carboxylic acid
Traditional IUPAC Name	(3R,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexane-1-carboxylic acid
Formula	C16H18O9
InChI	InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14?,16?/m1/s1
InChI Key	GYFFKZTYYAFCTR-AVXJPILUSA-N
Molecular weight	354.311
Exact mass	354.09508216
SMILES	O[C@@H]1CC(O)(C[C@@H](O)C1OC(=O)\C=C\C1=CC(O)=C(O)C=C1)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 4-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 4-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 4-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 4-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 4-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 4-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