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
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) Sources: https://www.hindawi.com/journals/ecam/2016/7823541/ |
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Target ID: CHEMBL3471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9449274 |
0.3 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. | 1998 Jan |
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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 |
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A new caffeoyl quinic acid from aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase. | 2000 Nov |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.hindawi.com/journals/ecam/2016/7823541/
B16-F10 melanocytes were treated with 25 and 50 uM of 4,5-dicaffeoylquinic acid in order to test the inhibitory effect of the compound on melanogenesis. The same concentrations were applied for 48 h in a cell viability assay.
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14534-61-3
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5281780
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45777W94HK
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89886-31-7
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SUBSTANCE RECORD