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Endostatin

Endostatin

Synopsis, 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

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 Formula	C₉H₁₀N₂O₂
Molecular Weight	178.19 g/mol
XLogP3	1.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	178.074227566 g/mol
Monoisotopic Mass	178.074227566 g/mol
Topological Polar Surface Area	49.7 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	188
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.