Compound: Calanolide A
SMILES: O=c1oc2c(c3OC(C=Cc3c4c2[C@@H](O)[C@H](C)[C@H](O4)C)(C)C)c(c1)CCC
InChIKey: NIDRYBLTWYFCFV-FMTVUPSXSA-N
Synonyms: Calanolide A, (+)-Calanolide A, 142632-32-4, S5A9TQN46W, NSC 675451, NSC-650886, CHEBI:65552, DTXSID601316787, (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, 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-, (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, RefChem:573327, DTXCID501746614, NSC 661122, CALANOLIDEA, CHEMBL267447, NSC650886, NSC675451, NSC-675451, (10R,11S,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, 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-, (10R,11S,12S)-, UNII-S5A9TQN46W, NSC 650886, NSC-664737, 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-, (10R,11S,12S)-, (+)-calnolide A, (+/-) Calanolide A, GlyTouCan:G84432BD, cid_1201, SCHEMBL140017, orb1700928, (+)-Calanolide A (synthetic), SCHEMBL30075237, NIDRYBLTWYFCFV-FMTVUPSXSA-N, G84432BD, BDBM50002662, MFCD00867485, AKOS015962188, DB04886, AC-16067, CS-0066526, NS00068706, C09147, Q5018528, (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-one, (10R,11S,12S)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-6H,10H-dipyrano[2,3-f;2'',3''-h]chromen-2-one, 12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-6H,10H-dipyrano[2,3-f;2'',3''-h]chromen-2-one(Calanolide A), InChI=1/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/s
Theoretical properties:
molecular_formula: C22H26O5
molecular_weight: 370.4 g/mol
exact_mass: 370.17802393 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 27
topological_polar_surface_area: 65 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "(+)-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.", "chebi": "An organic heterotetracyclic compound that is 11,12-dihydro-2<em>H</em>,6<em>H</em>,10<em>H</em>-dipyrano[2,3-<em>f</em>:2',3'-<em>h</em>]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 10<i>R</i>,11<i>S</i>,12<i>S</i> stereoisomer). Isolated from <em>Calophyllum lanigerum</em> var <em>austrocoriaceum</em> and <em>Calophyllum brasiliense</em>, it exhibits potent activity against HIV-1 reverse transcriptase.", "chembl": "CALANOLIDE A is a small molecule listed in the ChEMBL database and has reached clinical trial phase 1.0.", "wikipedia": "Calanolide A is an experimental non-nucleoside reverse transcriptase inhibitor (NNRTI). This compound was extracted from the tree Calophyllum lanigerum, of variety austrocoriaceum, in Lundu, Malaysian state of Sarawak in 1992 by United States National Cancer Institute (NCI). Due to rarity of the raw materials and low yield of the active ingredient, total synthesis of the compound was devised in 1996.  For the same reason, its sister compound (-)-Calanolide B (also known as Costatolide) have been touted as replacement. As a result of the discovery of Calanolide A, Sarawak Medichem pharmaceuticals company was established as a joint venture between US-based MediChem Research Inc and Craun Research Sdn Bhd, a company owned by the Sarawak state government. In 2006, Craun Research acquired Sarawak MediChem. In 2016, Craun Research announced the completion of Phase I clinical trials for Calanolide A."}