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(O)=C(O)C=C2)C(O)=O)OC(=O)\C=C\C3=CC(O)=C(O)C=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 19 Target ID: CHEMBL3471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9449274	Inhibitor 8297		0.66 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9449274	Primary		Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20570715	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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	8540756
Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase.	1996 Jun 25	8692814
Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase.	1996 Oct	8863829
Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase.	1998 Jan	9449274
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	9986720
Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet.	2005	16029149
Antiviral activities of purified compounds from Youngia japonica (L.) DC (Asteraceae, Compositae).	2006 Jun 30	16469463

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 `Sat Dec 16 08:54:05 GMT 2023` Edited by `admin` on `Sat Dec 16 08:54:05 GMT 2023`
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

DTXSID00424282