基本情報
- CAS
142632-32-4- 標準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- 分子式
- C22H26O5
- 平均分子量
- 370.4 g/mol
- 単同位体質量
- 370.17802393
名称と識別子
- 優先名称
- (+)-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
- 現地名
- (10R)-11,12-ジヒドロ-12α-ヒドロキシ-4-プロピル-6,6,10α,11β-テトラメチル-2H,6H,10H-ベンゾ[1,2-b:3,4-b′:5,6-b′′]トリピラン-2-オン
- 英語名
- Calanolide a
- 分子式
- C22H26O5
- 分子量
- 370.44
名称と別名
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
名称をさらに表示
カラノリドA4-プロピル-6,6,10α,11β-テトラメチル-12α-ヒドロキシ-11,12-ジヒドロ-2H,6H,10H-ベンゾ[1,2-b:3,4-b′:5,6-b′′]トリピラン-2-オン(10R)-11,12-ジヒドロ-12α-ヒドロキシ-4-プロピル-6,6,10α,11β-テトラメチル-2H,6H,10H-ベンゾ[1,2-b:3,4-b′:5,6-b′′]トリピラン-2-オン(10R,11S,12S)-12-ヒドロキシ-6,6,10,11-テトラメチル-4-プロピル-6,10,11,12-テトラヒドロ-2H-1,5,9-トリオキサトリフェニレン-2-オン(+)-カラノリドANSC675451NSC-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)-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-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-oneRefChem:573327DTXCID501746614NSC 661122CALANOLIDEACHEMBL267447
データベース識別子
- CAS
142632-32-4- PubChem CID
- 64972
- DTXSID
DTXSID601316787- ChEMBL
CHEMBL267447- ChEBI
CHEBI:65552- UNII
- S5A9TQN46W
- Nikkaji
- J500.414D
物性
構造計算による物性
- XLogP
- 3.8
- 極性表面積
- 65 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 5
- 回転可能結合数
- 2
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 666
化学と産業
薬理情報
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.
応用分野
使用(+)-Calanolide A is an experimental non-nucleoside reverse transcriptase inhibitor. It has potent anti-HIV activity.
上流・下流製品情報
上流原料
下流製品
サプライヤー21 社
上海策嵘生物科技有限公司[email protected]
济南百隆化学有限公司[email protected] · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
上海尺水药物研究有限公司[email protected] 13564957716 · [email protected]
上海珂华生物科技有限公司021-60455363 18019463053 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
苏州美石生物科技有限公司1173954148q · [email protected]
Standardpharm Co. Ltd.86-714-3992388 · [email protected]
泰迩生物医药泰州有限公司052386810091 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
武汉峰耀同辉化学制品有限公司027-87466105 15377573527 · [email protected]
上海与昂生物科技有限公司021-58111628 15800915896 · [email protected]
TargetMol中国（陶术生物）4008200310 15002144251 · [email protected]
北京新研汇医药研发有限公司13969155946 · [email protected]
湖北清北云研医药科技有限责任公司18162595016; 18162595016 · [email protected]
山东子易医药有限公司13173053288 · [email protected]
関連反応
11 件
化合物ノート
読み込み中…