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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H24O12
Molecular Weight 516.4518
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of 3,4-DICAFFEOYLQUINIC ACID

SMILES

c1cc(c(cc1/C(/[H])=C(\[H])/C(=O)O[C@]2([H])C[C@](C[C@]([H])([C@]2([H])OC(=O)/C(/[H])=C(\[H])/c3ccc(c(c3)O)O)O)(C(=O)O)O)O)O

InChI

InChIKey=UFCLZKMFXSILNL-RVXRWRFUSA-N
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

HIDE SMILES / InChI

Molecular Formula C25H24O12
Molecular Weight 516.4518
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 2
Optical Activity UNSPECIFIED

3,4-Dicaffeoylquinic acid is a component of Brazilian green propolis water extract, green coffee beans and other plants. It was reported to have antivirus activity against Influenza A Virus. The compound was also shown to inhibit AngII-induced rVSMC proliferation and migration, probably through downregulating the Akt, JNK and part of the ERK1/2 pathways, in which the anti-oxidant property plays an important role. 3,4-Dicaffeoylquinic acid possesses a high binding affinity to plasma proteins, making it less preferable as a drug candidate as this characteristic would affect diffusion or transport across cell membranes, limiting pharmacological actions. 3,4-Dicaffeoylquinic acid is also a selective inhibitor of human immunodeficiency virus type 1 integrase.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.71 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cell cycle arrest and apoptosis induced by methyl 3,5-dicaffeoyl quinate in human colon cancer cells: Involvement of the PI3K/Akt and MAP kinase pathways.
2011 Oct 15
Anti-hepatitis B virus effect and possible mechanism of action of 3,4-o-dicaffeoylquinic Acid in vitro and in vivo.
2012
Patents

Sample Use Guides

In a preclinical study, mice infected with influenza A virus were given 3,4-dicaffeoylquinic acid at a dose of 50 mg twice/kg/day. In a model of liver disease, mice received 5 and 10 mg/kg orally.
Route of Administration: Oral
In an anti-influenza virus assay, MDCK cells (2*10(5)/well) were cultured in MEM that contained 10% fetal bovine serum, 60 U/mL of penicillin, and 60 ug/mL of streptomycin for 24 hrs on 96-well plates, washed with PBS, and infected with 20 to 200 TCID50 A/WSN/33 virus in the presence of 0, 10, 30, 100, 300 ug/ml of 3,4-dicaffeoylquinic acid. The compound was added almost simultaneously in an assay medium, MEM that was supplemented with 1% BSA, 1% DMSO, and 6.25 ug/mL trypsin. Cell cultures were maintained without medium exchange at 37 degrees Celsius, 5% CO2 for 48 hrs.
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:33:29 UTC 2021
Edited
by admin
on Sat Jun 26 02:33:29 UTC 2021
Record UNII
E57A0DKE0B
Record Status Validated (UNII)
Record Version
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Name Type Language
3,4-DICAFFEOYLQUINIC ACID
Common Name English
3,4-DI-O-CAFFEOYLQUINIC ACID
Common Name English
3,4-DICQA
Common Name English
CYCLOHEXANECARBOXYLIC ACID, 3,4-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,5-DIHYDROXY-, (1R,3R,4S,5R)-
Systematic Name English
Code System Code Type Description
CAS
89886-30-6
Created by admin on Sat Jun 26 02:33:29 UTC 2021 , Edited by admin on Sat Jun 26 02:33:29 UTC 2021
PRIMARY
PUBCHEM
6474309
Created by admin on Sat Jun 26 02:33:29 UTC 2021 , Edited by admin on Sat Jun 26 02:33:29 UTC 2021
PRIMARY
CAS
57378-72-0
Created by admin on Sat Jun 26 02:33:29 UTC 2021 , Edited by admin on Sat Jun 26 02:33:29 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
FDA UNII
E57A0DKE0B
Created by admin on Sat Jun 26 02:33:29 UTC 2021 , Edited by admin on Sat Jun 26 02:33:29 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Methanol extracts of stevia dry leaves were directly used for LC-MS analysis. Efficient separation and resolution were achieved with diphenyl packing and acetonitrile/water as solvent in the HPLC method. Negative ion mode was used for all MS measurements.