Molecular Identity
Calanolide A
(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
PubChem CID: 64972
(+)-calanolide A 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 10R,11S,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.
2D Structure
Properties
C22H26O5
Molecular Formula
370.40
Molecular Weight
g/mol
370.1780
Exact Mass
Da
3.8
XLogP
Drug-like (Lipinski: < 5)
65
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
5
H-Bond Acceptors
666
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
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(+)-(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(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-one
Data from PubChem (NCBI)
This platform is for informational purposes only and does not constitute medical advice. Always consult a qualified healthcare professional.
Drug Network
Trials and conditions connected to Calanolide A
Loading drug network...