3,5-DI-O-CAFFEOYLQUINIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H24O12
Molecular Weight	516.4509
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure of 3,5-DI-O-CAFFEOYLQUINIC ACID

Structure Search

SMILES

O[C@H]1[C@@H](C[C@@](O)(C[C@H]1OC(=O)\C=C\C2=CC=C(O)C(O)=C2)C(O)=O)OC(=O)\C=C\C3=CC=C(O)C(O)=C3

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	516.4509
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.hindawi.com/journals/ecam/2016/4138263/

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 integrase 20 Target ID: CHEMBL3471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9449274	Inhibitor 8504		0.66 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9449274	Primary		Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20570715	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antiviral activities of purified compounds from Youngia japonica (L.) DC (Asteraceae, Compositae).	2006-06-30	16469463
A novel inhibitor of respiratory syncytial virus isolated from ethnobotanicals.	2005-12	16280176
Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet.	2005	16029149
A new caffeoyl quinic acid from aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase.	2000-11	11086919
Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication.	1999-02-11	9986720
Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase.	1998-01	9449274
Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase.	1996-10	8863829
Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase.	1996-06-25	8692814
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.	1995-08	8540756

Sample Use Guides

In Vivo Use Guide

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 Vitro Use Guide

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 `Mon Mar 31 22:22:32 GMT 2025` Edited by `admin` on `Mon Mar 31 22:22:32 GMT 2025`
Record UNII	ND94C5E75K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3,5-DICAFFEOYLQUINIC ACID

Preferred Name

English

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

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

DTXSID00424282