Top-53
基本情報
- CAS
148262-19-5- 標準SMILES
COc1cc([C@@H]2c3cc4c(cc3[C@@H](CCN(C)CCN(C)C)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O- InChIKey
KLCCMMSKRMSMKI-QVNMXXJYSA-N- 分子式
- C28H36N2O7
- 平均分子量
- 512.6 g/mol
- 単同位体質量
- 512.25225149
概要
TOP-53 is a furonaphthodioxole that is 4'-demethyldeoxypodophyllotoxin which is substituted at position 4 of the C-ring by a 2-{[2-(dimethylamino)ethyl](methyl)amino}ethyl group. While structurally related to etoposide, TOP-53 is significantly more toxic to non-small cell lung cancer cells, more active at generating chromosomal breaks, and displays improved cellular uptake and pharmacokinetics in animal lung tissues. It has a role as an antineoplastic agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a member of phenols, a gamma-lactone, an organic heterotetracyclic compound, a furonaphthodioxole and a tertiary amino compound.
名称と識別子
- 優先名称
- Top-53
- IUPAC
- (5R,5aR,8aR,9S)-9-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-6-one
- 英語名
- [5R-(5alpha,5abeta,8aalpha,9beta)]-9-[2-[N-[2-(Dimethylamino)ethyl]-N-methylamino]ethyl]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6-one
- 分子式
- C28H36N2O7
- 分子量
- 512.59
名称と別名
TOP-53Top 536L4LBD7SCFTOP53CHEBI:134547RefChem:190409148262-19-5(5R,5aR,8aR,9S)-9-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-6-oneUNII-6L4LBD7SCFTOP-53 FREE BASESCHEMBL20800121DTXSID10933355
名称をさらに表示
Free alkaliTOP-53 (free base)Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[2-[[2-(dimethylamino)ethyl]methylamino]ethyl]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-[5R-(5alpha,5abeta,8aalpha,9beta)]-9-[2-[N-[2-(Dimethylamino)ethyl]-N-methylamino]ethyl]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6-one
4-(2-((2-dimethylaminoethyl)methylamino)ethyl)-4'-O-demethyl-4-desoxypodophyllotoxin(5R,5AR,8AR,9S)-9-(2-((2-(DIMETHYLAMINO)ETHYL)METHYLAMINO)ETHYL)-5,8,8A,9-TETRAHYDRO-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE(5R,5aR,8aR,9S)-9-(2-{[2-(Dimethylamino)ethyl](methyl)amino}ethyl)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one(5R,5aR,8aR,9S)-9-(2-{[2-(dimethylamino)ethyl](methyl)amino}ethyl)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one4'-demethyl-4beta-(2-{N-[2-(N',N'-dimethylamino)ethyl]-N-methylamino}ethyl)-4-desoxypodophyllotoxin9-(2-{[2-(Dimethylamino)ethyl](methyl)amino}ethyl)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-oneFURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE, 9-(2-((2-(DIMETHYLAMINO)ETHYL)METHYLAMINO)ETHYL)-5,8,8A,9-TETRAHYDRO-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, (5R,5AR,8AR,9S)-FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE, 9-(2-((2-(DIMETHYLAMINO)ETHYL)METHYLAMINO)ETHYL)-5,8,8A,9-TETRAHYDRO-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.BETA.))-
物性
構造計算による物性
- XLogP
- 3
- 極性表面積
- 89.9 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 9
- 回転可能結合数
- 9
- 重原子数
- 37
- 形式電荷
- 0
- 複雑度
- 770
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