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2068-78-2 分子结构
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sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

ChemBase编号:72588
分子式:C46H58N4O14S
平均质量:923.03612
单一同位素质量:922.36702356
SMILES和InChIs

SMILES:
c1(cc2c(cc1[C@@]1(c3c(c4c([nH]3)cccc4)CCN3C[C@H](C1)C[C@@](C3)(O)CC)C(=O)OC)[C@@]13[C@@H](N2C=O)[C@]([C@@H]([C@]2([C@@H]1N(CC3)CC=C2)CC)OC(=O)C)(C(=O)OC)O)OC.S(=O)(=O)(O)O
Canonical SMILES:
OS(=O)(=O)O.O=CN1c2cc(OC)c(cc2[C@]23[C@@H]1[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@]1([C@@H]3N(CC2)CC=C1)CC)[C@]1(C[C@H]2CN(CCc3c1[nH]c1c3cccc1)C[C@](C2)(O)CC)C(=O)OC
InChI:
InChI=1S/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6;1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3;(H2,1,2,3,4)/t28?,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1
InChIKey:
AQTQHPDCURKLKT-FCIBFBFCSA-N

引用这个纪录

CBID:72588 http://www.chembase.cn/molecule-72588.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
IUPAC传统名
sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
sulfuric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
别名
长春新碱 硫酸盐
醛基长春碱 硫酸盐
长春新碱 硫酸盐
长春醛碱 硫酸盐
长春新碱 硫酸酯
Vincristine sulfate salt
22-Oxovincaleukoblastine sulfate salt
Leurocristine sulfate salt
Vincrex
Vincristine Sulfate
leurocristine
Oncovin
Vincasar PFS
VCR
Vincristine sulfate
CAS号
2068-78-2
EC号
218-190-0
MDL号
MFCD00084729
Beilstein号
3924631
PubChem SID
24278774
24900771
162037513
PubChem CID
5388992

理论计算性质

理论计算性质

JChem
Acid pKa 10.849017  质子受体
质子供体 LogD (pH = 5.5) -2.3829613 
LogD (pH = 7.4) 1.1448158  Log P 3.128179 
摩尔折射率 221.4804 cm3 极化性 87.836975 Å3
极化表面积 171.17 Å2 可自由旋转的化学键 10 
里宾斯基五规则 false 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
DMSO expand 查看数据来源
methanol: soluble20 mg/mL expand 查看数据来源
外观
white to off-white powder expand 查看数据来源
保存条件
-20°C expand 查看数据来源
RTECS编号
OH6340000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
联合国危险货物编号
2811 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
2 expand 查看数据来源
危险公开号
63-25-62-68 expand 查看数据来源
安全公开号
22-24/25 expand 查看数据来源
36/37-45 expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H300-H341-H361fd expand 查看数据来源
GHS警示性声明
P264-P281-P301 + P310 expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
RID/ADR
UN 2811 6.1/PG 2 expand 查看数据来源
保存温度
-20°C expand 查看数据来源
2-8°C expand 查看数据来源
作用靶点
Microtubule Formation expand 查看数据来源
纯度
≥95.0% (HPLC) expand 查看数据来源
95.0-105.0% (HPLC) expand 查看数据来源
成盐信息
H2SO4 expand 查看数据来源
Sulfate expand 查看数据来源
适用性
meets USP testing specifications expand 查看数据来源
杂质
≤10% water expand 查看数据来源
≤12% ethanol(actual content given on label) expand 查看数据来源
Empirical Formula (Hill Notation)
C46H56N4O10 · H2SO4 expand 查看数据来源
分类
Genuine Natural Compounds expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
Selleck Chemicals -  S1241 external link
Research Area: Cancer
Biological Activity:
Vincristine Sulfate is a kind of microtubule function inhibitor with IC50 of 10.4±1.1, 28.1±3.4, 22.4±2.1 µM for HL-60, Bel7402, HO-8910, respectively. It is the sulfate salt of a natural alkaloid isolated from the plant Vinca rosea Linn with antimitotic and antineoplastic activities. Vincristine binds irreversibly to microtubules and spindle proteins in S phase of the cell cycle and interferes with the formation of the mitotic spindle, thereby arresting tumor cells in metaphase. The IC50 and IC90 of vincristine for the 4 vaccine-associated feline sarcoma (VAFS) cell lines were between 0.005 to 0.039 µg/ml and 0.045 to 1.027 µg/ml, respectively .This agent also depolymerizes microtubules and may also interfere with amino acid, cyclic AMP, and glutathione metabolism. [1][2][3]
Sigma Aldrich -  V8879 external link
Application
Vincristine is an antitumor alkaloid isolated from Vinca Rosea. It is used to treat acute leukaemia, malignant lymphoma, Hodgkin′s disease, acute erythraemia, acute panmyelosis, breast cancer, Kaposi’s sarcoma and testicular cancer. Vincristine is widely used in cancer research. It is used to study multi-drug resistance. It is used to inhibit cell cycle progression at M-phase and to inhibit monoamine oxidase (MAO) 1.
Biochem/physiol Actions
Vincristine is a plant alkaloid that inhibits microtubule assembly by binding tubulin and inducing coiled spiral aggregate formation. It arrests cell cycle in G2/M-phase by blocking mitotic spindle formation2. Vincristine triggers Raf-1 activation, phosphorylation of bcl-2-family proteins, induction of p53 expression, and apoptosis in several tumor cell lines. It inhibits VEGF production in leukemia cell lines. It is a substrate for Pgp and CYP3A4. MRP1 transports vincristine in an ATP- and GSH-dependent manner. Vincristine has some immunosuppressant effect. Vincristine may also interfere with amino acid, cyclic AMP, and glutathione metabolism, calmodulin-dependent Ca2+-transport, cellular respiration, and nucleic acid and lipid biosynthesis1.
Sigma Aldrich -  V8388 external link
Application
Widely used in cancer research. In studies on multi-drug resistance. Used to inhibit cell cycle progression at M-phase. Used to inhibit monoamine oxidase (MAO).

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Banerji N et al. Am J Vet Res. 2002;63(5):728-32
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专利

专利

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