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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-10-07 19:33:23 UTC

Update Date

2022-03-07 03:18:16 UTC

HMDB ID

HMDB0240453

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Feruloylquinic acid

Description

4-Feruloylquinic acid (4-FQA) (CAS: 2613-86-7) 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. Coffee, especially green or raw coffee, is a major source of chlorogenic acids (CGA). CGAs have been associated with a range of health benefits including a reduction in the risk of cardiovascular disease, diabetes type 2, and Alzheimer's disease. Major CGAs in coffee include 3-, 4-, and 5-feruloylquinic acids (PMID: 19022950 ). 4-FQA has been detected in the plasma and urine of humans who have ingested coffee (PMID: 19460943 ).

Structure

MOL SDF PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₂₀O₉

Average Molecular Weight

368.3353

Monoisotopic Molecular Weight

368.110732238

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

96646-16-1

SMILES

Not Available

InChI Identifier

InChI=1S/C17H20O9/c1-25-13-6-9(2-4-10(13)18)3-5-14(21)26-15-11(19)7-17(24,16(22)23)8-12(15)20/h2-6,11-12,15,18-20,24H,7-8H2,1H3,(H,22,23)/b5-3+/t11-,12-,15-,17+/m1/s1

InChI Key

VTMFDSJJVNQXLT-KSQYBWRXSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19460943)

Excreta

Biofluid or Excreta

Urine (PMID: 19460943)

Source

Exogenous

Exogenous (HMDB: HMDB0240453)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Drupe

Berry

Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Strawberry (FooDB: FOOD00083)
Highbush blueberry (FooDB: FOOD00191)
Jostaberry (FooDB: FOOD00257)

Fruits (HMDB: HMDB0240453)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)

Vegetables (HMDB: HMDB0240453)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0240453)

Tea

Tea products (HMDB: HMDB0240453)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Predicted Molecular Properties

Not Available

Predicted Chromatographic Properties

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.25 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4724 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.89 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1355.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	201.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	87.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	57.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	325.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	316.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	406.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	678.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	252.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1066.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	429.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	213.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	211.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Feruloylquinic acid	COC1=C(O)C=CC(\C=C\C(=O)O[C@H]2[C@H](O)C[C@@](O)(C[C@H]2O)C(O)=O)=C1	5329.5	Standard polar	33892256
4-Feruloylquinic acid	COC1=C(O)C=CC(\C=C\C(=O)O[C@H]2[C@H](O)C[C@@](O)(C[C@H]2O)C(O)=O)=C1	3127.5	Standard non polar	33892256
4-Feruloylquinic acid	COC1=C(O)C=CC(\C=C\C(=O)O[C@H]2[C@H](O)C[C@@](O)(C[C@H]2O)C(O)=O)=C1	3310.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Feruloylquinic acid,1TMS,isomer #1	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O)C[C@H]2O)=CC=C1O[Si](C)(C)C	3202.2	Semi standard non polar	33892256
4-Feruloylquinic acid,1TMS,isomer #2	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O	3175.1	Semi standard non polar	33892256
4-Feruloylquinic acid,1TMS,isomer #3	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]2O)=CC=C1O	3198.3	Semi standard non polar	33892256
4-Feruloylquinic acid,1TMS,isomer #4	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O	3175.1	Semi standard non polar	33892256
4-Feruloylquinic acid,1TMS,isomer #5	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O[Si](C)(C)C)C[C@H]2O)=CC=C1O	3136.3	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #1	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3157.6	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #10	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O	3068.3	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #2	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]2O)=CC=C1O[Si](C)(C)C	3185.3	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #3	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O[Si](C)(C)C)C[C@H]2O)=CC=C1O[Si](C)(C)C	3126.2	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #4	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3157.6	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #5	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C)C[C@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O	3132.5	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #6	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O[Si](C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O	3144.3	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #7	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O	3068.3	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #8	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C[C@H]2O)=CC=C1O	3097.4	Semi standard non polar	33892256
4-Feruloylquinic acid,2TMS,isomer #9	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O	3144.3	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #1	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C)C[C@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3125.2	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #10	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O	3050.4	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #2	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O[Si](C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3143.6	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #3	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3079.2	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #4	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C[C@H]2O)=CC=C1O[Si](C)(C)C	3088.3	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #5	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3143.6	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #6	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3079.2	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #7	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O	3109.2	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #8	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C)C[C@](O)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O	3034.3	Semi standard non polar	33892256
4-Feruloylquinic acid,3TMS,isomer #9	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O	3050.4	Semi standard non polar	33892256
4-Feruloylquinic acid,4TMS,isomer #1	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3146.0	Semi standard non polar	33892256
4-Feruloylquinic acid,4TMS,isomer #2	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C)C[C@](O)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3080.0	Semi standard non polar	33892256
4-Feruloylquinic acid,4TMS,isomer #3	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3079.9	Semi standard non polar	33892256
4-Feruloylquinic acid,4TMS,isomer #4	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3079.9	Semi standard non polar	33892256
4-Feruloylquinic acid,4TMS,isomer #5	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C)C[C@](O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O	3065.3	Semi standard non polar	33892256
4-Feruloylquinic acid,5TMS,isomer #1	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C)C[C@](O[Si](C)(C)C)(C(=O)O[Si](C)(C)C)C[C@H]2O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3114.9	Semi standard non polar	33892256
4-Feruloylquinic acid,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O)C[C@H]2O)=CC=C1O[Si](C)(C)C(C)(C)C	3479.5	Semi standard non polar	33892256
4-Feruloylquinic acid,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3432.6	Semi standard non polar	33892256
4-Feruloylquinic acid,1TBDMS,isomer #3	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]2O)=CC=C1O	3472.0	Semi standard non polar	33892256
4-Feruloylquinic acid,1TBDMS,isomer #4	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3432.6	Semi standard non polar	33892256
4-Feruloylquinic acid,1TBDMS,isomer #5	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O)=CC=C1O	3422.6	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3657.6	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #10	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3588.0	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #2	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]2O)=CC=C1O[Si](C)(C)C(C)(C)C	3691.6	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #3	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O)=CC=C1O[Si](C)(C)C(C)(C)C	3650.4	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #4	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3657.6	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #5	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C[C@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3625.8	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #6	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3636.2	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #7	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3588.0	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #8	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O)=CC=C1O	3610.5	Semi standard non polar	33892256
4-Feruloylquinic acid,2TBDMS,isomer #9	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3636.2	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C[C@](O)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3838.0	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #10	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3790.7	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #2	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3853.9	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #3	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3802.9	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #4	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O)=CC=C1O[Si](C)(C)C(C)(C)C	3824.4	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #5	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3853.9	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #6	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3802.9	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #7	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3830.6	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #8	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C[C@](O)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3763.1	Semi standard non polar	33892256
4-Feruloylquinic acid,3TBDMS,isomer #9	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3790.7	Semi standard non polar	33892256
4-Feruloylquinic acid,4TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4021.7	Semi standard non polar	33892256
4-Feruloylquinic acid,4TBDMS,isomer #2	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C[C@](O)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3960.7	Semi standard non polar	33892256
4-Feruloylquinic acid,4TBDMS,isomer #3	COC1=CC(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3974.2	Semi standard non polar	33892256
4-Feruloylquinic acid,4TBDMS,isomer #4	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3974.2	Semi standard non polar	33892256
4-Feruloylquinic acid,4TBDMS,isomer #5	COC1=CC(/C=C/C(=O)O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3969.8	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19460943	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19460943	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Stalmach A, Mullen W, Barron D, Uchida K, Yokota T, Cavin C, Steiling H, Williamson G, Crozier A: Metabolite profiling of hydroxycinnamate derivatives in plasma and urine after the ingestion of coffee by humans: identification of biomarkers of coffee consumption. Drug Metab Dispos. 2009 Aug;37(8):1749-58. doi: 10.1124/dmd.109.028019. Epub 2009 May 21. [PubMed:19460943 ]
Farah A, Monteiro M, Donangelo CM, Lafay S: Chlorogenic acids from green coffee extract are highly bioavailable in humans. J Nutr. 2008 Dec;138(12):2309-15. doi: 10.3945/jn.108.095554. [PubMed:19022950 ]

Showing metabocard for 4-Feruloylquinic acid (HMDB0240453)

MOL for HMDB0240453 (4-Feruloylquinic acid)

3D MOL for HMDB0240453 (4-Feruloylquinic acid)

3D SDF for HMDB0240453 (4-Feruloylquinic acid)

3D-SDF for HMDB0240453 (4-Feruloylquinic acid)

PDB for HMDB0240453 (4-Feruloylquinic acid)

3D PDB for HMDB0240453 (4-Feruloylquinic acid)

SMILES for HMDB0240453 (4-Feruloylquinic acid)

INCHI for HMDB0240453 (4-Feruloylquinic acid)

Structure for HMDB0240453 (4-Feruloylquinic acid)

3D Structure for HMDB0240453 (4-Feruloylquinic acid)

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized