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500-44-7 分子结构
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(2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid

ChemBase编号:926
分子式:C8H10N2O4
平均质量:198.176
单一同位素质量:198.06405681
SMILES和InChIs

SMILES:
OC(=O)[C@@H](N)Cn1cc(O)c(=O)cc1
Canonical SMILES:
OC(=O)[C@H](Cn1ccc(=O)c(c1)O)N
InChI:
InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)/t5-/m0/s1
InChIKey:
WZNJWVWKTVETCG-YFKPBYRVSA-N

引用这个纪录

CBID:926 http://www.chembase.cn/molecule-926.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
(2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid
IUPAC传统名
mimosine
别名
(S)-α-Amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid
L-Mimosine from Koa hoale seeds
β-[N-(3-Hydroxy-4-pyridone)-α-aminopropionic acid
L-MIMOSINE
L-Mimosine
Leucaenine
Leucaenol
Leucenine
Leucenol
Mimosin
Mimosine
CAS号
500-44-7
EC号
207-905-1
MDL号
MFCD00075909
PubChem SID
46505895
160964389
24896541
PubChem CID
440473

数据来源

数据来源

所有数据来源 商品来源 非商品来源

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 1.9351499  质子受体
质子供体 LogD (pH = 5.5) -2.959101 
LogD (pH = 7.4) -2.9720697  Log P -2.9591975 
摩尔折射率 48.6582 cm3 极化性 18.249966 Å3
极化表面积 103.86 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -2.43  LOG S -1.18 
溶解度 1.31e+01 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
疏水性(logP)
-2.5 expand 查看数据来源
保存条件
2-8°C expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) 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
20/21/22 expand 查看数据来源
安全公开号
22-36 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
H302-H312-H332 expand 查看数据来源
GHS警示性声明
P280 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
纯度
≥98% expand 查看数据来源
≥98% expand 查看数据来源
质检报告
下载链接 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich
MP Biomedicals -  02159973 external link
Purity: >98%
A rare amino acid from plants which reversibly blocks the G1 phase of the cell cycle. Deoxyhypusine hydroxylation inhibitor that subsequently inhibits eukaryote initiation factor 5-A.
DrugBank -  DB01055 external link
Item Information
Drug Groups approved
Description 3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca. [PubChem]
Pharmacology Mimosine inhibits DNA synthesis at the level of elongation of nascent chains by altering deoxyribonucleotide metabolism. It arrests the cell cycle in the late G(1) phase.
Affected Organisms
Humans and other mammals
Protein Binding >99.5%
External Links
Wikipedia
Sigma Aldrich -  M0253 external link
Biochem/physiol Actions
L-Mimosine is a plant amino acid and potential inhibitor of the cell cycle giving rise to growth arrest in G1-phase. An iron chelator that inhibits DNA replication in mammalian cells. Has been shown to have apoptotic activity in xenotransplanted human pancreatic cancer. L-Mimosine is also used as a hypoxia-mimetic agent to stabilize Hypoxia Inducible Factor 1 (HIF-1). L-Mimosine stabilizes HIF-1 through the inhibition of Prolyl Hydroxylases (PHDs) which target HIF-1 through degradation. The mechanism of inhibition is likely through the chelation of Fe2+ bound to the active site of PHD which is required for enzymatic activity.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Hanauske-Abel, H.M., et al., Biochim. Biophys. Acta , 1221 : 115 (1994).
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专利

专利

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互联网资源

互联网资源

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