基本情報
- CAS
477-47-4- 標準SMILES
COc1cc([C@@H]2c3cc4c(cc3[C@H](O)[C@H]3COC(=O)[C@@H]23)OCO4)cc(OC)c1OC- InChIKey
YJGVMLPVUAXIQN-HAEOHBJNSA-N- 分子式
- C22H22O8
- 平均分子量
- 414.4 g/mol
- 単同位体質量
- 414.13146766
概要
Picropodophyllotoxin is an organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents. It has a role as an antineoplastic agent, a tyrosine kinase inhibitor, an insulin-like growth factor receptor 1 antagonist and a plant metabolite. It is a lignan, an organic heterotetracyclic compound and a furonaphthodioxole.
名称と識別子
- 優先名称
- Picropodophyllin
- IUPAC
- (5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
- 現地名
- (5R)-5,8,8aβ,9-テトラヒドロ-5β-(3,4,5-トリメトキシフェニル)-9β-ヒドロキシフロ[3',4':6,7]ナフト[2,3-d]-1,3-ジオキソール-6(5aβH)-オン
- 英語名
- (-)PPP
- 分子式
- C22H22O8
- 分子量
- 414.41
名称と別名
PicropodophyllinPicropodophyllotoxin477-47-4AXL1717cyclolignan PPPpicro-podophyllinAXL-1717Picropodophyllin (PPP)0F35AOI227NSC36407NSC-36407Podophyllotoxin picropodophyllin
名称をさらに表示
(5R)-5,8,8aβ,9-テトラヒドロ-5β-(3,4,5-トリメトキシフェニル)-9β-ヒドロキシフロ[3',4':6,7]ナフト[2,3-d]-1,3-ジオキソール-6(5aβH)-オンピクロポドフィロトキシンピクロポドフィリン(5R)-5,8,8aβ,9-テトラヒドロ-9β-ヒドロキシ-5β-(3,4,5-トリメトキシフェニル)フロ[3',4':6,7]ナフト[2,3-d]-1,3-ジオキソール-6(5aβH)-オンメタカビル[(2S,5R)-5-(2-アミノ-6-メトキシ-9H-プリン-9-イル)オキソラン-2-イル]メタノール(5R)-5,8,8aβ,9-テトラヒドロ-9β-ヒドロキシ-5β-(3,4,5-トリメトキシフェニル)フロ[3′,4′:6,7]ナフト[2,3-d]-1,3-ジオキソール-6(5aβH)-オン(5R)-5,8,8aβ,9-テトラヒドロ-5β-(3,4,5-トリメトキシフェニル)-9β-ヒドロキシフロ[3′,4′:6,7]ナフト[2,3-d]-1,3-ジオキソール-6(5aβH)-オン(10R,11S,15R,16R)-16-ヒドロキシ-10-(3,4,5-トリメトキシフェニル)-4,6,13-トリオキサテトラシクロ[7.7.0.03,7.011,15]ヘキサデカ-1,3(7),8-トリエン-12-オン2-アミノ-9-(2,3-ジデオキシ-β-D-アラビノフラノシル)-6-メトキシ-9H-プリン
物性
構造計算による物性
- XLogP
- 2
- 極性表面積
- 92.7 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 8
- 回転可能結合数
- 4
- 重原子数
- 30
- 形式電荷
- 0
- 複雑度
- 629
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
189.52 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
190.9 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 225 · 225-227℃
- 比旋光度
- 20 · D20 +9.4° (c = 0.7 in chloroform)
- 沸点
- 453.31 °C · 453.31°C (rough estimate)
- 比重(密度)
- 1.37 · 1.370
- 屈折率
- 1.448 · 1.4480 (estimate)
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- 2 O: · H2O: 可溶
- 外見
- 粉
- 酸解離定数(Pka)
- 13.26 · 13.26±0.40(Predicted)
- 色
- 白い
- 水溶解度
- 2 O: · H2O: soluble
- 安定性
- -20 °C · -20°C の DMSO 溶液で最大 1 か月間保存できます。
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 3 (100%)
毒性情報
Exposure RoutesTopical application of 0.05 mL of 0.5% podofilox solution to external genitalia did not result in detectable serum levels. Applications of 0.1 to 1.5 mL resulted in peak serum levels of 1 to 17 ng/mL one to two hours after application.
Toxicity Summary
Etoposide, a semisynthetic derivative of podofilox, induces DNA breakage through its inhibition of topoisomerase II. The drug is most active in the late S and early G2 phases of the cell cycle. Teniposide is an analog with very similar pharmacologic characteristics. Podofilox derivatives display binding activity to the enzyme topoisomerase II during the late S and early G2 stage. For instance, etoposide binds and stabilizes the temporary break caused by the enzyme, disrupts the reparation of the break through which the double-stranded DNA passes, and consequently stops DNA unwinding and replication. Mutants resistant to either podofilox, or to its topoisomerase II inhibitory derivatives such as etoposide (VP-16), have been described in Chinese hamster cells. The mutually exclusive cross-resistance patterns of these mutants provide a highly specific mean to distinguish the two kinds of podofilox derivatives. Mutant Chinese hamster cells resistant to podofilox are affected in a protein P1 that was later identified as the mammalian HSP60 or chaperonin protein. (Wikipedia)
化学と産業
薬理情報
Metabolism/MetabolitesHalf Life: 1.0 to 4.5 hours.
用途と製造
UsesFor treatment of external genital warts (<i>Condyloma acuminatum</i>).
応用分野
使用Insulin growth factor 1 receptor inhibitor, antineoplastic
一般的な説明Poly(2,5-bis(3-sulfonatopropoxy)-1,4-phenylene, disodium salt-alt-1,4-phenylene) (PPP-OPSO3) is a water soluble conjugating polymer that can be used as a donor molecule. It has a poly(p-phenylene) skeleton with each repeating unit having two phenylene groups. It can be used for a variety of optoelectronic applications.
サプライヤー159 社
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
武汉英诺医药科技有限公司
関連反応
2 件
化合物ノート
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