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
SMILES
O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H]1OC(=O)\C=C\C3=CC=C(O)C(O)=C3)C(O)=O
InChI
InChIKey=UFCLZKMFXSILNL-PSEXTPKNSA-N
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,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 |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 2 |
| Optical Activity | UNSPECIFIED |
4,5-Dicaffeoylquinic acid is an active component naturally occurring in many plants such as Helichrysum populifolium, Ipomoea batatas, Centella asiatica, Aster scaber, Artemisia capillaris and green coffee beans to name a few. It was shown to be a pigmentation inhibitor in melanocytes and the effect was explained by suppression of melanogenesis (possibly via TRP-1 gene). 4,5-Dicaffeoylquinic acid is also an 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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P17643 Gene ID: 7306.0 Gene Symbol: TYRP1 Target Organism: Homo sapiens (Human) |
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Target ID: CHEMBL3471 |
0.3 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching. | 1997 Mar 14 |
|
| 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 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:54:07 GMT 2023
by
admin
on
Sat Dec 16 08:54:07 GMT 2023
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| Record UNII |
45777W94HK
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| Record Status |
Validated (UNII)
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| Record Version |
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14534-61-3
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NON-SPECIFIC STEREOCHEMISTRY | |||
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5281780
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45777W94HK
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89886-31-7
Created by
admin on Sat Dec 16 08:54:07 GMT 2023 , Edited by admin on Sat Dec 16 08:54:07 GMT 2023
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| Related Record | Type | Details | ||
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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 |
