Costatolide
Basic information
- CAS
909-14-8- Standard SMILES
CCCc1cc(=O)oc2c3c(c4c(c12)OC(C)(C)C=C4)O[C@@H](C)[C@H](C)[C@@H]3O- InChIKey
NIDRYBLTWYFCFV-PZROIBLQSA-N- Molecular formula
- C22H26O5
- Average molar mass
- 370.4 g/mol
- Monoisotopic mass
- 370.17802393
Overview
(-)-calanolide B is an organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10S,11R,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase. It has a role as a HIV-1 reverse transcriptase inhibitor and a plant metabolite. It is a delta-lactone, a secondary alcohol, a cyclic ether and an organic heterotetracyclic compound.
Names & identifiers
- Preferred name
- Costatolide
- IUPAC
- (16S,17R,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 B
- Molecular formula
- C22H26O5
- Molecular weight
- 370.43884
Names & synonyms
Costatolide(16S,17R,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(16S,17R,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-oneRefChem:128201(2S)-4-chloro-2-((Z)-1-chloroprop-1-en-2-yl)-5-methyl-2,3-dihydropyran-6-one63023-58-5(-)-Calanolide BCostatolide (Calophyllum)909-14-8CHEMBL7187(+)-(10S,11R,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(10S,11R,12S)-11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H,10H-benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-one
Show more names
(10S,11R,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-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-,(10S,11R,12S)-2H,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-,(10S,11R,12S)-orb1741093SCHEMBL8927756SCHEMBL29397227CHEBI:65553DTXSID50920087
Properties
Computed structural properties
- 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
Chemistry & industry
Pharmacology
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
DescriptionCostatolide is isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase. It has a role as a HIV-1 reverse transcriptase inhibitor and a plant metabolite. It is a delta-lactone, a cyclic ether, a secondary alcohol and an organic heterotetracyclic compound.
Additional notes
DefinitionChEBI: (-)-calanolide B is an organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10S,11R,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase. It has a role as a HIV-1 reverse transcriptase inhibitor and a plant metabolite. It is a delta-lactone, a cyclic ether, a secondary alcohol and an organic heterotetracyclic compound.
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