CAS 161753-49-7 (+)-12-Oxocalanolide A (HCID 463613)

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Basic information

CAS: 161753-49-7
Standard SMILES: CCCc1cc(=O)oc2c3c(c4c(c12)OC(C)(C)C=C4)O[C@H](C)[C@@H](C)C3=O
InChIKey: HQVBDUZROQMWRN-VXGBXAGGSA-N
Molecular formula: C22H24O5
Average molar mass: 368.4 g/mol
Monoisotopic mass: 368.16237387

Names & identifiers

Preferred name: (+)-12-Oxocalanolide A
IUPAC: (16R,17R)-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-pentaene-4,18-dione
English name: Nsc670365
Molecular formula: C22H24O5
Molecular weight: 368.42

Names & synonyms

12-Oxocalanolide A(+)-12-Oxocalanolide A161753-49-712-OxocalanolideNSC670365(+-)-12-Oxocalanolide ACHEMBL269090183904-55-4NSC 670365(16R,17R)-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-pentaene-4,18-dione2H,6H,12H-Benzo(1,2-b:3,4-b':5,6-b'')tripyran-2,12-dione, 10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-rel-trans-(+)-2H,6H,12H-Benzo(1,2-b:3,4-b':5,6-b'')tripyran-2,12-dione, 10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-

Show more names

Aids051610Aids-051610151005-67-3 (Deleted)trans-10,11-Dihydro-6,6,10,11-tetramethyl-4-propyl-2H,6H,12H-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione

2H,6H,12H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione, 10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-rel-trans-(+)-2H,6H,12H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione, 10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-(+/-)-Trans-ketoneZ8MM7J5DWJ(1)-12-Oxocalanolide A12-Oxocalanolide A, (+)-orb1991156SCHEMBL7027286

Properties

Computed structural properties

XLogP: 4.2
Topological polar surface area: 61.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 27
Formal charge: 0
Complexity: 705

Physicochemical properties

Boiling point: 546.7 · 546.7±50.0 °C(Predicted)
Density: 1.176 · 1.176±0.06 g/cm3(Predicted)

Chemistry & industry

Applications

Uses12-Oxocalanolide A (compound 6) is a potent inhibitor of reverse transcriptase from human immunodeficiency virus type 1 (HIV-1) with an IC50 and EC50 of 2.8 and 12 μM, respectively. 12-Oxocalanolide A is the analogue of Calanolide[1].