U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 4,5-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-PSEXTPKNSA-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

4,5-Dicaffeoylquinic acid is an active component naturally occurring in many plants such as Helichrysum populifolium, Ipomoea batatas, Centella asiatica, Aster scaber, Artemisia capillaris and green coffee beans to name a few. It was shown to be a pigmentation inhibitor in melanocytes and the effect was explained by suppression of melanogenesis (possibly via TRP-1 gene). 4,5-Dicaffeoylquinic acid is also an inhibitor of human immunodeficiency virus type 1 integrase and can be a promising agent for the treatment of patients with HIV infection.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P17643
Gene ID: 7306.0
Gene Symbol: TYRP1
Target Organism: Homo sapiens (Human)
0.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Differential inhibition of reverse transcriptase and cellular DNA polymerase-alpha activities by lignans isolated from Chinese herbs, Phyllanthus myrtifolius Moon, and tannins from Lonicera japonica Thunb and Castanopsis hystrix.
1995 Aug
Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase.
1996 Oct
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
1997 Mar 14
Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase.
1998 Jan
Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.
1999 Feb 11
A new caffeoyl quinic acid from aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase.
2000 Nov
Antiviral activities of purified compounds from Youngia japonica (L.) DC (Asteraceae, Compositae).
2006 Jun 30
Anti-hepatitis B virus effect and possible mechanism of action of 3,4-o-dicaffeoylquinic Acid in vitro and in vivo.
2012

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
B16-F10 melanocytes were treated with 25 and 50 uM of 4,5-dicaffeoylquinic acid in order to test the inhibitory effect of the compound on melanogenesis. The same concentrations were applied for 48 h in a cell viability assay.
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:33:30 UTC 2021
Edited
by admin
on Sat Jun 26 02:33:30 UTC 2021
Record UNII
45777W94HK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4,5-DICAFFEOYLQUINIC ACID
Common Name English
4,5-DICQA
Common Name English
CYCLOHEXANECARBOXYLIC ACID, 3,4-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,5-DIHYDROXY-, (1S,3R,4R,5R)-
Systematic Name English
4,5-DI-O-CAFFEOYLQUINIC ACID
Common Name English
Code System Code Type Description
CAS
14534-61-3
Created by admin on Sat Jun 26 02:33:30 UTC 2021 , Edited by admin on Sat Jun 26 02:33:30 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
PUBCHEM
5281780
Created by admin on Sat Jun 26 02:33:30 UTC 2021 , Edited by admin on Sat Jun 26 02:33:30 UTC 2021
PRIMARY
FDA UNII
45777W94HK
Created by admin on Sat Jun 26 02:33:30 UTC 2021 , Edited by admin on Sat Jun 26 02:33:30 UTC 2021
PRIMARY
CAS
89886-31-7
Created by admin on Sat Jun 26 02:33:30 UTC 2021 , Edited by admin on Sat Jun 26 02:33:30 UTC 2021
PRIMARY
Related Record Type Details
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.
PARENT -> CONSTITUENT ALWAYS PRESENT