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

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

Description

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	Inhibitor 8,297		0.66 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 151	Primary		Basic research	Unknown
Alzheimer’s disease 272	Primary		Preclinical	Unknown

PubMed

PubMed

Show entries

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

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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%.

Show entries

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

Showing 1 to 5 of 15 entries

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Code System

Code

Type

Description

EPA CompTox

DTXSID00424282

PRIMARY

CAS

900249-68-5

ALTERNATIVE

CAS

1245638-27-0

NON-SPECIFIC STEREOCHEMISTRY

RS_ITEM_NUM

1348033

PRIMARY

CAS

89919-62-0

PRIMARY

Showing 1 to 5 of 8 entries

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SUBSTANCE RECORD


					ND94C5E75K

3,5-DI-O-CAFFEOYLQUINIC ACID