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Details

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

SHOW SMILES / InChI
Structure of 3,5-DI-O-CAFFEOYLQUINIC ACID

SMILES

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

InChI

InChIKey=KRZBCHWVBQOTNZ-PSEXTPKNSA-N
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,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 2 / 2
E/Z Centers 2
Optical Activity UNSPECIFIED

3,5-Dicaffeoylquinic acid is an active component naturally occurring in many plants such as Helichrysum populifolium, Ipomoea batatas, Centella asiatica, Aster scaber and green coffee beans to name a few. It is a selective 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
0.66 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase.
1996 Jun 25
Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase.
1996 Oct
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

Sample Use Guides

In a preclinical model of Alzheimer’s disease, mice were orally administered with 3,5-dicaffeoylquinic acid mixed with drinking water (6.7 mg/kg/day) for 1 month using oral administration tube and syringe.
Route of Administration: Oral
In a viability assay, SH-SY5Y cells were treated with 3,5-dicaffeoylquinic acid (20 uM) and exposed to 2 uM Abeta1-42 for 72 h. The drug was shown to protect the cells from death and the cell viability significantly increased to 106.5%.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:25:23 UTC 2021
Edited
by admin
on Sat Jun 26 09:25:23 UTC 2021
Record UNII
ND94C5E75K
Record Status Validated (UNII)
Record Version
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Name Type Language
3,5-DI-O-CAFFEOYLQUINIC ACID
Common Name English
3,5-DI-O-(E)-CAFFEOYLQUINIC ACID
Common Name English
(1S,3R,4S,5R)-3,5-BIS(((E)-3-(3,4-DIHYDROXYPHENYL)ACRYLOYL)OXY)-1,5-DIHYDROXYCYCLOHEXANE-1-CARBOXYLIC ACID
Systematic Name English
CJ-4-16-4
Common Name English
(1.ALPHA.,3R,4.ALPHA.,5R)-3,5-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4-DIHYDROXYCYCLOHEXANECARBOXYLIC ACID
Systematic Name English
TRANS 3,5-O-DICAFFEOYLQUINIC ACID
Common Name English
CYCLOHEXANECARBOXYLIC ACID, 3,5-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4-DIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-
Systematic Name English
QUINIC ACID 3,5-DI-O-CAFFEATE
Common Name English
3,5-DICQA
Common Name English
(E,E)-3,5-DI-O-CAFFEOYLQUINIC ACID
Common Name English
3,5-DICAFFEOYLQUINIC ACID
Common Name English
CYCLOHEXANECARBOXYLIC ACID, 3,5-BIS((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4-DIHYDROXY-, (1R-(1.ALPHA.,3.ALPHA.(E),4.ALPHA.,5.BETA.(E)))-
Systematic Name English
3,5-DICAFFEOYLQUININIC ACID
Common Name English
(-)-3,5-DICAFFEOYLQUINIC ACID
Common Name English
CYCLOHEXANECARBOXYLIC ACID, 1,4-DIHYDROXY-3,5-BIS(((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-, (1.ALPHA.,3R,4.ALPHA.,5R)-
Systematic Name English
Code System Code Type Description
EPA CompTox
89919-62-0
Created by admin on Sat Jun 26 09:25:23 UTC 2021 , Edited by admin on Sat Jun 26 09:25:23 UTC 2021
PRIMARY
CAS
900249-68-5
Created by admin on Sat Jun 26 09:25:23 UTC 2021 , Edited by admin on Sat Jun 26 09:25:23 UTC 2021
ALTERNATIVE
CAS
1245638-27-0
Created by admin on Sat Jun 26 09:25:23 UTC 2021 , Edited by admin on Sat Jun 26 09:25:23 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
CAS
89919-62-0
Created by admin on Sat Jun 26 09:25:23 UTC 2021 , Edited by admin on Sat Jun 26 09:25:23 UTC 2021
PRIMARY
FDA UNII
ND94C5E75K
Created by admin on Sat Jun 26 09:25:23 UTC 2021 , Edited by admin on Sat Jun 26 09:25:23 UTC 2021
PRIMARY
CAS
2450-53-5
Created by admin on Sat Jun 26 09:25:23 UTC 2021 , Edited by admin on Sat Jun 26 09:25:23 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
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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