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D-赤型鞘氨醇-1-磷酸, GPR12 的激动剂;GPR3 的激动剂;GPR63 的激动剂;GPR6 的激动剂;P2RY10 的激动剂;S1P 1 受体的激动剂;S1P 2 受体的激动剂;S1P 3 受体的激动剂;S1P 4 受体的激动剂;S1P 5 受体的激动剂

S1P受体的内源性信号鞘脂和激动剂
  • CAS编号: 26993-30-6
  • 分子式: C18H38NO5P
  • 分子量: 379.472
  • PubChem编号: 5283560
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货号 (SKU) 包装规格 是否现货 价格 数量
D130606-1mg
1mg 现货 Stock Image
D130606-5mg
5mg 现货 Stock Image

基本描述

英文别名 (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl dihydrogen phosphate | 4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), (2S,3R,4E)- | 4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), (R-(R*,S*-(E)))- | Sphingosine 1-phosphate, >=95%, pow
规格或纯度 Moligand™, ≥98%
英文名称 D-erythro-sphingosine-1-phosphate
生化机理 一种与 S1P1 和 S1P3 受体结合的脂质第二信使。调动细胞内 Ca2+ 储存并降低细胞内的 cAMP。S1P 可刺激内皮细胞迁移,但会抑制其他类型细胞的迁移。诱导血管生成。内源性信号鞘脂和 S1P 受体(EDG-GPCR)的激动剂。通过独立于 IP 3 受体的途径从细胞内贮存调动 Ca 2+。激活 MAPK 通路。调节多种细胞反应并促进血管生成。
应用 A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12.
储存温度 -20°C储存,充氩
运输条件 超低温冰袋运输
作用类型 激动剂
作用机制 GPR12 的激动剂;GPR3 的激动剂;GPR63 的激动剂;GPR6 的激动剂;P2RY10 的激动剂;S1P 1 受体的激动剂;S1P 2 受体的激动剂;S1P 3 受体的激动剂;S1P 4 受体的激动剂;S1P 5 受体的激动剂
备注 Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. For delivery of sphingosine-1-phosphate to cells, prepare a 125μM stock in 4mg/ml BSA as follows: Dissolve sphingosine-1-phosphate (S-1-P) in methanol (0.5 mg/ml). This may require boiling (65°C), with occasional replacement of evaporated methanol. Crushing of solid prior to addition of methanol and crushing and stirring during heating is helpful. Aliquot desired amounts of methanol stock to tubes. Evaporate the solvent with a stream of nitrogen, swirling to deposit a thin film on the inside of the tube. Aliquots may be stored at -20 °C at this point or dissolved with enough 4mg/ml BSA (fatty acid free Bovine Serum Albumin in water; 37°C, 30 min. with repeated vortexing) to make 125 µM stock. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
产品介绍

D-erythro-Sphingosine-1-phosphate(S1P) is a polar sphingolipid metabolite which regulates diverse cellular responses including cell growth, survival and migration. S1P was reported to stimulate DNA synthesis and cell division in quiescent cultures of Swiss 3T3 fibroblasts and to trigger the dual signal transduction pathways of calcium mobilization and PC-PLD (phospholipase D) activation. S1P serves as a second messenger for intracellular calcium mobilization in U-937 cells and decreases cellular cAMP. Recent studies show that S1P is a G-protein-coupled receptor (GPCR) ligand for the EDG-1 family, including EDG-1, -3, -5, -6 and -8. This bioactive lipid mediator has been shown to stimulate the ERK pathway and to also counteract the ceramide-induced activation of stress-activated protein kinase (SAPK/JNK). Researchers have also found that S1P is a strong inhibitor of cell motility and phagokinesis in B16 melanoma cells. Additionally, it induces rapid and transient tyrosine phosphorylation of epidermal growth factor receptor (EGFR) and c-Met in gastric cancer cells. S1P has also been known as a tumor-promoting lipid. Sμggested to be an activator of GPR3, GPR6, and GPR12. D-erythro-Sphingosine-1-phosphate is an activator of EDG-1, EDG-3, EDG-2, EDG-4 and EDG-5.A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12.

D-erythro-Sphingosine-1-phosphate(S1P) is a polar sphingolipid metabolite which regulates diverse cellular responses including cell growth, survival and migration. S1P was reported to stimulate DNA synthesis and cell division in quiescent cultures of Swiss 3T3 fibroblasts and to trigger the dual signal transduction pathways of calcium mobilization and PC-PLD (phospholipase D) activation. S1P serves as a second messenger for intracellular calcium mobilization in U-937 cells and decreases cellular cAMP. Recent studies show that S1P is a G-protein-coupled receptor (GPCR) ligand for the EDG-1 family, including EDG-1, -3, -5, -6 and -8. This bioactive lipid mediator has been shown to stimulate the ERK pathway and to also counteract the ceramide-induced activation of stress-activated protein kinase (SAPK/JNK). Researchers have also found that S1P is a strong inhibitor of cell motility and phagokinesis in B16 melanoma cells. Additionally, it induces rapid and transient tyrosine phosphorylation of epidermal growth factor receptor (EGFR) and c-Met in gastric cancer cells. S1P has also been known as a tumor-promoting lipid. Suggested to be an activator of GPR3, GPR6, and GPR12. D-erythro-Sphingosine-1-phosphate is an activator of EDG-1, EDG-3, EDG-2, EDG-4 and EDG-5.
A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12.

纯度 ≥98%

关联靶点(人)

GPR12 Tbio G 蛋白偶联受体 12(G-protein coupled receptor 12) (0 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
GPR3 Tchem G蛋白偶联受体3(G-protein coupled receptor 3) (0 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
GPR63 Tchem 可能的 G 蛋白偶联受体 63(Probable G-protein coupled receptor 63) (0 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
GPR6 Tchem G 蛋白偶联受体 6(G-protein coupled receptor 6) (0 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
S1PR5 Tclin 鞘氨醇 1-磷酸受体 5(Sphingosine 1-phosphate receptor 5) (12 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
S1PR2 Tchem 鞘氨醇 1-磷酸受体 2(Sphingosine 1-phosphate receptor 2) (11 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
S1PR4 Tclin 鞘氨醇 1-磷酸受体 4(Sphingosine 1-phosphate receptor 4) (9 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
S1PR1 Tclin 鞘氨醇 1-磷酸受体 1(Sphingosine 1-phosphate receptor 1) (21 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
S1PR3 Tclin 鞘氨醇 1-磷酸受体 3(Sphingosine 1-phosphate receptor 3) (19 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
P2RY10 Tchem 假定的 P2Y 嘌呤受体 10(Putative P2Y purinoceptor 10) (1 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
ABL1 Tclin Tyrosine-protein kinase ABL (18331 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ADRB2 Tclin Beta-2 adrenergic receptor (11824 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
AGTR1 Tclin Type-1 angiotensin II receptor (5176 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CSNK1D Tchem Casein kinase I delta (4546 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
S1PR4 Tclin Sphingosine 1-phosphate receptor Edg-6 (1041 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
S1PR3 Tclin Sphingosine 1-phosphate receptor Edg-3 (2543 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
S1PR2 Tchem Sphingosine 1-phosphate receptor Edg-5 (1593 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
S1PR1 Tclin Sphingosine 1-phosphate receptor Edg-1 (5806 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CDK2 Tchem Cyclin-dependent kinase 2 (9050 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GLP1R Tclin Glucagon-like peptide 1 receptor (111429 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
S1PR5 Tclin Sphingosine 1-phosphate receptor Edg-8 (813 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
C5AR1 Tclin C5a anaphylatoxin chemotactic receptor (2677 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
U2OS (164939 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CX3CR1 Tchem C-X3-C chemokine receptor 1 (1686 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
FPR2 Tchem Lipoxin A4 receptor (3472 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
FFAR4 Tchem G-protein coupled receptor 120 (2999 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
BRD4 Tchem Bromodomain-containing protein 4 (13122 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GPR35 Tchem G-protein coupled receptor 35 (2643 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
BRPF1 Tchem Peregrin (2217 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
S1PR2 Tchem Sphingosine 1-phosphate receptor Edg-5/Sphingosine 1-phosphate receptor Edg-3 (2 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HEK-293T (167025 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

关联靶点(其它种属)

Aplnr Apelin receptor (201 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Mapk1 MAP kinase ERK2 (650 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Fgfr3 Fibroblast growth factor receptor 3 (21 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Gpr119 Glucose-dependent insulinotropic receptor (270 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

作用机制

作用机制 Action Type target ID Target Name Target Type Target Organism Binding Site Name 参考文献

名称和识别符

分子类型 小分子
IIUPAC Name [(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate
INCHI 1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1
InChi Key DUYSYHSSBDVJSM-KRWOKUGFSA-N
Smiles CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O
Isomeric SMILES CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)N)O
分子量 379.472
Reaxy-Rn 29141682
Reaxys-RN link address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=29141682&ln=

化学和物理性质

溶解性 Soluble in warm acetic acid, 0.3M NaOH (~4 mg/ml), and methanol: THF: water (6:3:1) (>0.5 mg/ml). Insoluble in water.
敏感性 对光和空气、湿度敏感
熔点 179-189°C
分子量 379.500 g/mol
XLogP3 1.900
氢键供体数Hydrogen Bond Donor Count 4
氢键受体数Hydrogen Bond Acceptor Count 6
可旋转键计数Rotatable Bond Count 17
精确质量Exact Mass 379.249 Da
单同位素质量Monoisotopic Mass 379.249 Da
拓扑极表面积Topological Polar Surface Area 113.000 Ų
重原子数Heavy Atom Count 25
形式电荷Formal Charge 0
复杂度Complexity 372.000
同位素原子数Isotope Atom Count 0
定义的原子立体中心计数Defined Atom Stereocenter Count 2
未定义的原子立体中心计数Undefined Atom Stereocenter Count 0
定义的键立体中心计数Defined Bond Stereocenter Count 1
未定义的键立体中心计数Undefined Bond Stereocenter Count 0
所有立体化学键的总数The total count of all stereochemical bonds 1
共价键合单元计数Covalently-Bonded Unit Count 1

安全和危险性(GHS)

象形图 GHS07
信号词 警告
危险声明

H315: 引起皮肤刺激

H319: 引起严重眼睛刺激

H335: 可能引起呼吸道刺激

预防措施声明

P261: 避免吸入灰尘/烟雾/气体/雾/蒸汽/喷雾

P264: 处理后要彻底洗手。

P271: 仅在室外或通风良好的地方使用。

P280: 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。

P321: 特殊处理(请参阅此标签上的...)。

P302+P352: 如皮肤沾染:用水充分清洗。

P304+P340: 如误吸入:将人转移到空气新鲜处,保持呼吸舒适体位。

P305+P351+P338: 如进入眼睛:用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出,取出隐形眼镜。继续冲洗。

P362+P364: 脱掉沾污的衣服,清洗后方可重新使用。

P405: 密闭存放

P403+P233: 存放在通风良好的地方。保持容器密闭。

P501: 将内容物/容器处理到。。。

P264+P265: 处理后彻底洗手[和…]。不要触摸眼睛。

P337+P317: 如果眼睛刺激持续:寻求医疗帮助。

P332+P317: 如果出现皮肤刺激:请寻求医疗帮助。

P319: 如果你感到不适,请寻求医疗帮助。

WGK Germany 3
个人防护装备 dust mask type N95 (US), Eyeshields, Gloves

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K2229376 分析证书 D130606
K2229502 分析证书 D130606
H2205076 分析证书 D130606
C2228024 分析证书 D130606
H2205077 分析证书 D130606
C2228035 分析证书 D130606

此产品的引用文献

引用文献

1. Xiaomei Wu, Bin Pang, Jianwei You, Leiye Yu, Ruobing Ren, Hongyang Wang, Li Chen.  (2023)  An LC-MS-based workflow measures the export activity of S1P transporters.  BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS,  668  (118).  [PMID:37245292] [10.1016/j.bbrc.2023.05.014]
2. Xinhua Liu, Youteng Qin, Liyun Dong, Ziyi Han, Tianning Liu, Ying Tang, Yun Yu, Jingjie Ye, Juan Tao, Xuan Zeng, Jun Feng, Xian-Zheng Zhang.  (2023)  Living symbiotic bacteria-involved skin dressing to combat indigenous pathogens for microbiome-based biotherapy toward atopic dermatitis.  Bioactive Materials,  21  (253).  [PMID:36157249] [10.1016/j.bioactmat.2022.08.019]
3. Qianyu Chen, Yayun Zhang, Langjie Ye, Shuai Gong, Hong Sun, Guanyong Su.  (2021)  Identifying active xenobiotics in humans by use of a suspect screening technique coupled with lipidomic analysis.  ENVIRONMENT INTERNATIONAL,  157  (106844).  [PMID:34455192] [10.1016/j.envint.2021.106844]
4. Qianyu Chen, Yayun Zhang, Jianhua Li, Guanyong Su, Qi Chen, Zhen Ding, Hong Sun.  (2021)  Serum concentrations of neonicotinoids, and their associations with lipid molecules of the general residents in Wuxi City, Eastern China.  JOURNAL OF HAZARDOUS MATERIALS,  413  (125235).  [PMID:33581671] [10.1016/j.jhazmat.2021.125235]
5. Li YAO, Yu-Xia YANG, Hui CAO, Huan-Huan REN, Zheng NIU, Ling SHI.  (2020)  Osthole attenuates pulmonary arterial hypertension by the regulation of sphingosine 1-phosphate in rats.  Chinese Journal of Natural Medicines,  18  (308).  [PMID:32402408] [10.1016/S1875-5364(20)30038-8]

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