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129-56-6 分子结构
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14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9(16),10,12-heptaen-8-one

ChemBase编号:1554
分子式:C14H8N2O
平均质量:220.22612
单一同位素质量:220.06366289
SMILES和InChIs

SMILES:
c1cc2c(cc1)c(=O)c1c3c(ccc1)[nH]nc23
Canonical SMILES:
O=c1c2ccccc2c2c3c1cccc3[nH]n2
InChI:
InChI=1S/C14H8N2O/c17-14-9-5-2-1-4-8(9)13-12-10(14)6-3-7-11(12)15-16-13/h1-7H,(H,15,16)
InChIKey:
ACPOUJIDANTYHO-UHFFFAOYSA-N

引用这个纪录

CBID:1554 http://www.chembase.cn/molecule-1554.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
14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9(16),10,12-heptaen-8-one
14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9(16),10,12-heptaen-8-one
14,15-diazatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),2(7),3,5,9(16),10,12-heptaen-8-one
14,15-diazatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),2,4,6,9(16),10,12-heptaen-8-one
IUPAC传统名
14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9(16),10,12-heptaen-8-one
14,15-diazatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),2(7),3,5,9(16),10,12-heptaen-8-one
1,9-pyrazoloanthrone
别名
Anthra[1,9-cd]pyrazol-6(2H)-one
SP600125
1,9-Pyrazoloanthrone
Anthra[1,9-cd]pyrazol-6(2H)-one
Pyrazolanthrone
Pyrazoleanthrone
SP 600125
C.I. 70300
NSC 75890
1,9-Pyrazoloanthrone
2,6-Dihydroanthra/1,9-Cd/Pyrazol-6-One
SP600125
1,9-Pyrazoloanthrone
Anthrapyrazolone
SP600125
2H-Dibenzo[cd,g]indazol-6-one
CAS号
129-56-6
129-56-6
EC号
204-955-6
MDL号
MFCD00022289
PubChem SID
46507936
24278395
160965011
PubChem CID
8515
CHEMBL
7064
Chemspider ID
8201
DrugBank ID
DB01782
维基百科标题
1,9-Pyrazoloanthrone

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 10.020759  质子受体
质子供体 LogD (pH = 5.5) 2.8154738 
LogD (pH = 7.4) 2.8144772  Log P 2.8154905 
摩尔折射率 65.3548 cm3 极化性 27.04146 Å3
极化表面积 45.75 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.76  LOG S -3.07 
溶解度 1.86e-01 g/l 

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
H2O: insoluble expand 查看数据来源
insoluble in water expand 查看数据来源
外观
yellow expand 查看数据来源
熔点
236 - 238°C expand 查看数据来源
281-282°C expand 查看数据来源
沸点
489.3°C @760mmHg expand 查看数据来源
闪点
246.8°C expand 查看数据来源
密度
1.463cm3 expand 查看数据来源
疏水性(logP)
3.231 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
RTECS编号
CB4585000 expand 查看数据来源
欧盟危险性物质标志
刺激性(Irritant) 刺激性(Irritant) (Xi) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
36/37/38 expand 查看数据来源
安全公开号
26-36 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
作用靶点
JNK expand 查看数据来源
相关基因信息
human ... JUN(3725), MAPK10(5602), MAPK9(5601) expand 查看数据来源
生物活性机理
Selective c-Jun N-terminal kinase (JNK) inhibitor expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
95% expand 查看数据来源
97% expand 查看数据来源
98% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
应用领域
Antineoplastic agent expand 查看数据来源
Empirical Formula (Hill Notation)
C14H8N2O expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
DrugBank -  DB01782 external link
Drug information: experimental
Selleck Chemicals -  S1460 external link
Research Area
Description Cancer
Biological Activity
Description SP600125 is a broad-spectrum JNK inhibitor for JNK1, JNK2 and JNK3 with IC50 of 40 nM, 40 nM and 90 nM, respectively.
Targets JNK1 JNK2 JNK3 Aurora A Flt3 TRKA
IC50 40 nM 40 nM 90 nM [1] 60 nM 90 nM 70 nM [4]
In Vitro SP600125 is originally characterized as a selective ATP-competitive inhibitor of c-Jun N-terminal kinase JNK. In Jurkat T cells, SP600125 inhibits the phosphorylation of c-Jun with IC50 of 5 μM to 10 μM. In CD4+ cells, such as Th0 cells isolated from either human cord or peripheral blood, SP600125 blocks cell activation and differentiation and inhibits the expression of inflammatory genes COX-2, IL-2, IL-10, IFN-γ, and TNF-α, with IC50 of 5 μM to 12 μM. [1]However, later studies reveal that SP600125 also suppresses aryl hydrocarbon receptor (AhR) [2], Mps1 [3], and a panel of other serine/threonine kinases, including Aurora kinase A, FLT3, MELK, and TRKA [4].In a mouse beta cells MIN6, SP600125 (20 μM) induces the phosphorylation of p38 MAPK and its downstream CREB-dependent promoter activation. [5]In HCT116 cells, SP600125 (20 μM) blocks the G2 phase to mitosis transition and induces endoreplication. This ability of SP600125 is independent of JNK inhibition, but due to its inhibition of CDK1-cyclin B activation upstream of Aurora A and Polo-like kinase 1. [6]
In Vivo In mice, SP600125 (15 mg/kg or 30 mg/kg) significantly inhibits lipopolysaccharide (LPS)-induced TNF-α expression and anti-CD3-induced apoptosis of CD4+ CD8+ thymocytes. [1]
Clinical Trials
Features
Protocol
Kinase Assay [4]
In Vitro Kinase Assays The potency of SP600125 towards kinases, including MPS1, JNK, and Aurora kinase A, is determined based on the specific measurement of radioactive phosphotransfer to the substrate. For each enzyme, the absolute Km values for ATP and the specific substrate are initially determined and each assay is then run at optimized [ATP] (2·αKm) and [substrate] (5·Km) concentrations. MPS1 activity is measured using 5 nM of MPS1 recombinant protein in 50 mM HEPES pH 7.5, 2.5 mM MgCl2, 1 mM MnCl2, 1 mM DTT, 3 μM NaVO3, 2 mM β-glycerophosphate, 0.2 mg/mL BSA, 200 μM P38-βtide substrate-peptide (KRQADEEMTGYVATRWYRAE), and 8 μM ATP with 1.5 nM 33P-γ-ATP. Ten serial 1:3 dilutions (from 30 μM to 1.5 nM) of SP600125 are tested and IC50 determined.
Cell Assay [4]
Cell Lines HCT116, A2780, and U2OS cells
Concentrations 0–5 μM, dissolved in 0.1% DMSO
Incubation Time 72 hours
Methods Cells are seeded in 384 well-plates. One day after seeding, the cells are treated with SP600125 for 72 hours and the plates are then processed using a CellTiter-Glo assay. Inhibitory activity is evaluated comparing treated versus control data and IC50 value of proliferation is calculated.
Animal Study [1]
Animal Models Mouse LPS/TNF model (female CD-1)
Formulation Dissolved in PPCES (30% PEG-400/20% polypropylene glycol/15% Cremophor EL/5% ethanol/30% saline)
Doses 15 or 30 mg/kg
Administration Administered via intravenous injection or orally
References
[1] Bennett BL, et al. Proc Natl Acad Sci U S A, 2001, 98(24), 13681-13686.
[2] Joiakim A, et al. Drug Metab Dispos, 2003, 31(11), 1279-1282.
[3] Schmidt M, et al. EMBO Rep, 2005, 6(9), 866-872.
[4] Colombo R, et al. Cancer Res, 2010, 70(24), 10255-64.
[5] Vaishnav D, et al. Biochem Biophys Res Commun, 2003, 307(4), 855-860.
[6] Kim JA, et al. Oncogene, 2010, 29(11), 1702-1716.
Sigma Aldrich -  S5567 external link
Biochem/physiol Actions
A novel and selective inhibitor of c-Jun N-terminal kinase (JNK)

参考文献

参考文献

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