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Basic information
- CAS
142632-32-4- Standard SMILES
CCCc1cc(=O)oc2c3c(c4c(c12)OC(C)(C)C=C4)O[C@H](C)[C@@H](C)[C@@H]3O- InChIKey
NIDRYBLTWYFCFV-FMTVUPSXSA-N- Molecular formula
- C22H26O5
- Average molar mass
- 370.4 g/mol
- Monoisotopic mass
- 370.17802393
Names & identifiers
- Preferred name
- (+)-Calanolide A
- IUPAC
- (16R,17S,18S)-18-hydroxy-10,10,16,17-tetramethyl-6-propyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaen-4-one
- English name
- Calanolide a
- Molecular formula
- C22H26O5
- Molecular weight
- 370.44
Names & synonyms
Calanolide A(+)-Calanolide A142632-32-4S5A9TQN46WNSC 675451NSC-650886CHEBI:65552DTXSID601316787(10R,11S,12S)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one(16R,17S,18S)-18-hydroxy-10,10,16,17-tetramethyl-6-propyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaen-4-one2H,6H,10H-Benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-one, 11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-, (10R-(10alpha,11beta,12alpha))-(+)-(10R,11S,12S)-10,11-TRANS-DIHYDRO-12-HYDROXY-6,6,10,11-TETRAMETHYL-4-PROPYL-2H,6H-BENZO(1,2-B:3,4-B':5,6-B'')TRIPYRAN-2-ONE
Show more names
NSC675451NSC-675451(+) Calanolide A(+)-(10R,11S,12S)-12-HYDROXY-6,6,10,11-TETRAMETHYL-4-PROPYL-11,12-DIHYDRO-2H,6H,10H-BENZO(1,2-B:3,4-B':5,6-B'']TRIPYRAN-2-ONE2H,6H,10H-Dipyrano[2,3-f:2',3'-h][1]benzopyran-2-one, 11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-, (10R,11S,12S)-
Properties
Computed structural propertiesFilling in
- XLogP
- 3.8
- Topological polar surface area
- 65 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 666
Physicochemical properties
- FDA UNII
- 5 A9TQN46W · S5A9TQN46W
Chemistry & industry
Pharmacology
Pharmacodynamics
Calanolide A is a new non-nucleoside reverse transcriptase inhibitor (NNRTI) derived from a plant found in the Malaysian rain forest. A related compound, calanolide B, also has anti-HIV activity. Both drugs are being developed by Sarawak Pharmaceuticals. The drug is metabolised by cytochrome P450 CYP3A, and its developers have suggested that drug levels may be enhanced if co-administered with ritonavir (Norvir). The drug is active in the test tube against HIV with the two most common NNRTI-related mutations, K103N and Y181C, and selects for a mutation which does not cause cross-resistance with any other NNRTIs currently under investigation. A substitution at codon Y188H of reverse transcriptase has been associated with 30-fold resistance to calanolide A in vitro (Quan 1999). The compound is essentially inactive against strains of the less common HIV type 2.
Mechanism of Action
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.
Biological Half-Life20 hours for 800mg
Metabolism/MetabolitesHepatic.
MeSH Pharmacological ClassificationAgents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS.
Applications
Uses(+)-Calanolide A is an experimental non-nucleoside reverse transcriptase inhibitor. It has potent anti-HIV activity.
Upstream & downstream products
Upstream raw materials
Related reactions
11 records
Compound notes
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