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Chemistry

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Also known as: N-methyl-n-phenacylnitrous amide, 55984-52-6, 187888-07-9, Ethanone, 2-(methylnitrosoamino)-1-phenyl-, 2-oxo-2-phenylethylmethylnitrosamine, Dtxsid10204557
Molecular Formula
C9H10N2O2
Molecular Weight
178.19  g/mol
InChI Key
AAFYOVPTFNNVDN-UHFFFAOYSA-N

Endostatin
Angiostatic proteins that are formed from proteolytic cleavage of COLLAGEN TYPE XVIII.
1 2D Structure

Endostatin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-methyl-N-phenacylnitrous amide
2.1.2 InChI
InChI=1S/C9H10N2O2/c1-11(10-13)7-9(12)8-5-3-2-4-6-8/h2-6H,7H2,1H3
2.1.3 InChI Key
AAFYOVPTFNNVDN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(CC(=O)C1=CC=CC=C1)N=O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Endostatins

2.2.2 Depositor-Supplied Synonyms

1. N-methyl-n-phenacylnitrous Amide

2. 55984-52-6

3. 187888-07-9

4. Ethanone, 2-(methylnitrosoamino)-1-phenyl-

5. 2-oxo-2-phenylethylmethylnitrosamine

6. Dtxsid10204557

7. Zinc5965474

2.3 Create Date
2005-08-09
3 Chemical and Physical Properties
Molecular Weight 178.19 g/mol
Molecular Formula C9H10N2O2
XLogP31.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass178.074227566 g/mol
Monoisotopic Mass178.074227566 g/mol
Topological Polar Surface Area49.7 Ų
Heavy Atom Count13
Formal Charge0
Complexity188
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in cancer/tumors (unspecified), macular degeneration, and diabetic retinopathy.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Angiogenesis Inhibitors

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)


Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


5.2 Mechanism of Action

Endostatin is an endogenous antitumor protein. Endostatin is a 20-kDa C-terminal fragment derived from type XVIII collagen which inhibits cell proliferation and migration, and induces endothelial cell apoptosis and cell cycle arrest. It is proposed that endostatin's effects are due to inhibition of vascular endothelial growth factor (VEGF) tyrosine phosphorylation of KDR/F1k-1 (VEGF receptor 2), the cell surface receptor for VEGF. VEGF is an important mediator of angiogensis. Endostatin additionally blocks activation of extracellular signal related kinases, or ERK, protein 38 mitogen activated protein kinase, or p38 MAPK (signal transduction pathways involving kinases that couple growth factors to cell surface receptors), as well as focal adhesion kinase (p125FAK). Studies are being done to determine if endostatin has possible impact on other pathways, and may also target E-selectin and block activity of metalloproteinases 2, 9 and 13. There is further research into a possible mechanistic link involving endostatin's angiogenic and zinc binding ability.


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