(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

• ChemBase编号: 1050
• 分子式: C22H22O8
• 平均质量: 414.40528
• 单一同位素质量: 414.13146766
• SMILES: O1C[C@H]2[C@@H]([C@@H](c3c([C@@H]2O)cc2OCOc2c3)c2cc(OC)c(OC)c(OC)c2)C1=O
• Canonical SMILES: COc1cc(cc(c1OC)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@H](c2c1cc1OCOc1c2)O
• InChI: InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1
• InChIKey: YJGVMLPVUAXIQN-XVVDYKMHSA-N

名称和登记号

名称

• IUPAC标准名: (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one; (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1,3(7),8-trien-12-one; (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1(9),2,7-trien-12-one
• IUPAC传统名: podofilox; (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1(9),2,7-trien-12-one; condylox
• 商标名: Podophyllotoxin 7; Podophyllotoxin
• 别名: Podophyllinic acid lactone; Podofilox; (5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; (-)-Podophyllotoxin; Condyline; Condylox; NSC 24818; Podofilox; Podophyllotoxin; Warticon; Podofilox; (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one; Podophyllotoxin; (5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one; 9-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDROFURO[3',4':6,7]NAPHTHO[2,3-D][1,3]DIOXOL-6(5AH)-ONE

登记号

• CAS号: 518-28-5; 477-47-4
• EC号: 208-250-4
• MDL号: MFCD00075290
• Beilstein号: 99163
• PubChem SID: 24277731; 24887649; 160964513; 46505716; 24888464
• PubChem CID: 10607

理论计算性质

JChem

• Acid pKa: 14.015751
• 质子受体: 7
• 质子供体: 1
• LogD (pH = 5.5): 1.6227983
• LogD (pH = 7.4): 1.6227982
• Log P: 1.6227983
• 摩尔折射率: 103.905 cm^3
• 极化性: 41.000076 Å^3
• 极化表面积: 92.68 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.37
• LOG S: -3.56
• 溶解度: 1.14e-01 g/l

分子性质

理化性质

• 溶解度: 100 mg/L; 120mg/L in Water; Acetone; Chloroform; Ethanol
• 外观: White to Off-White Solid
• 熔点: 154-158°C; 182 - 184°C; 183-184 °C(lit.)
• 比旋光度: [α]20/D -110.7°, c = 1 in chloroform; [α]20/D -132±4°, c = 1% in chloroform
• 疏水性(logP): 1.444; 1.5

安全信息

• 保存条件: -20°C Freezer, Under Inert Atmosphere
• 保存注意事项: Very Hygroscopic
• RTECS编号: LV2500000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 3462
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 21-25-36/37/38
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H310-H315-H319-H335
• GHS警示性声明: P261-P280-P302 + P350-P305 + P351 + P338-P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• 保存温度: 2-8°C

药理学性质

• 生物活性机理: Cell division inhibitor; Inhibitor of human DNA topoisomerase II; Reported to bind to tubulin

产品相关信息

• 纯度: ≥98%; ≥98.0% (HPLC); 95%
• 生物来源: Isol. from Podophyllum emodi, Diphylleia grayi and others
• 应用领域: Cytostatic
• Empirical Formula (Hill Notation): C22H22O8

详细说明

DrugBank - DB01179

• Drug Groups: approved
• Description: A lignan (lignans) found in podophyllin resin from the roots of podophyllum plants. It is a potent spindle poison, toxic if taken internally, and has been used as a cathartic. It is very irritating to skin and mucous membranes, has keratolytic actions, has been used to treat warts and keratoses, and may have antineoplastic properties, as do some of its congeners and derivatives. [PubChem]
• Indication: For treatment of external genital warts (Condyloma acuminatum).
• Pharmacology: Podofilox, also called podophyllotoxin, is a purer and more stable form of podophyllin in which only the biologically active portion of the compound is present. Podofilox is used to remove certain types of warts on the outside skin of the genital areas.
• Affected Organisms: Condyloma acuminatum
• Absorption: Topical 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.
• Half Life: 1.0 to 4.5 hours.
• External Links: Wikipedia; RxList; Drugs.com

DrugBank - DB08417

Drug information: experimental

Sigma Aldrich - P4405

Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
包装
100 mg in glass bottle
50 mg in poly bottle

Sigma Aldrich - 858447

Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
包装
1 g in glass bottle
100 mg in glass bottle

Sigma Aldrich - 81125

Biochem/physiol Actions
Inhibits microtubule assembly; antineoplastic.
Other Notes
Inhibitor of microtubule assembly. Useful tool for tubulin studies1,2,3

Toronto Research Chemicals - P681000

Skin treatment for genital warts caused by some types of HPVs.

参考文献

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