Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H26O5 |
| Molecular Weight | 370.4388 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC1=CC(=O)OC2=C1C3=C(C=CC(C)(C)O3)C4=C2[C@@H](O)[C@H](C)[C@@H](C)O4
InChI
InChIKey=NIDRYBLTWYFCFV-FMTVUPSXSA-N
InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1
| Molecular Formula | C22H26O5 |
| Molecular Weight | 370.4388 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Calanolide A is a new non-nucleoside reverse transcriptase inhibitor (NNRTI) originally extracted from a tropical tree (Calophyllum lanigerum) in the Malaysian rain forest. Viral life-cycle studies indicate that calanolide A acts early in the infection process, similar to the known HIV reverse transcriptase (RT) inhibitor 2', 3'-dideoxycytidine. In enzyme inhibition assays, calanolide A potently and selectively inhibits recombinant HIV type 1 RT but not cellular DNA polymerases or HIV type 2 RT within the concentration range tested. Phase I studies have found that calanolide A is well tolerated. Consequently, it has potential clinical applications in combination with other antiviral drugs to suppress HIV-1 mutants. Nevertheless, the development of calanolide A has been delayed due to its low therapeutic index (range: 16–279), non-ideal antiviral activity, and the complexity of its extraction from plants
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B. | 1996 Oct 25 |
|
| Sensitivity and resistance to (+)-calanolide A of wild-type and mutated forms of HIV-1 reverse transcriptase. | 1999 |
|
| Inhibition of HIV-1 reverse transcriptase and HIV-1 replication by Calophyllum coumarins and xanthones. | 2002 Jan |
|
| Safety and pharmacokinetic profile of multiple escalating doses of (+)-calanolide A, a naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy HIV-negative volunteers. | 2002 Nov-Dec |
|
| HIV-1 inhibitory compounds from Calophyllum brasiliense leaves. | 2004 Sep |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 04:58:02 UTC 2023
by
admin
on
Sat Dec 16 04:58:02 UTC 2023
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| Record UNII |
S5A9TQN46W
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID601316787
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650886
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S5A9TQN46W
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65552
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64972
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Calanolide A
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DB04886
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142632-32-4
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