| 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
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
| Molecular Formula | C25H24O12 |
| Molecular Weight | 516.4509 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| 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.
Originator
Approval Year
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 |
|
| 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 |
|
| A novel inhibitor of respiratory syncytial virus isolated from ethnobotanicals. | 2005 Dec |
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
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID00424282 | PRIMARY | |||
|
900249-68-5 | ALTERNATIVE | |||
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1245638-27-0 | NON-SPECIFIC STEREOCHEMISTRY | |||
|
1348033 | PRIMARY | |||
|
89919-62-0 | PRIMARY | |||
|
65751 | PRIMARY | |||
|
ND94C5E75K | PRIMARY | |||
|
2450-53-5 | NON-SPECIFIC STEREOCHEMISTRY |
| 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.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
