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Chemistry

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Also known as: Emapticap pegol, Olaptesed pegol, Nox-a12 free acid, Nox-e36 free acid, Emapticap pegol [inn], Olaptesed pegol [inn]

Molecular Formula

C₁₈H₃₇N₂O₁₀P

Molecular Weight

472.5 g/mol

InChI Key

QJAGBAPUFWBVSD-UHFFFAOYSA-N

Olaptesed Pegol is a 45-mer L-stereoisomer RNA oligonucleotide linked to a 40 kDa polyethyleneglycol that targets the small chemokine stromal cell-derived factor 1 (SDF-1 or CXCL12) with potential antineoplastic and hematopoietic stem cell-mobilization activities. SDF-1 targeted agent NOX-A12 specifically binds to SDF-1 thereby preventing the binding of SDF-1 to its receptors CXCR4 and CXCR7 blocking the subsequent receptor activation. This may prevent angiogenesis, tumor cell proliferation, invasion and metastasis and could sensitize tumor cells to chemotherapy. In addition, inhibition of SDF-1/CXCR4 interaction may induce mobilization of hematopoietic cells from the bone marrow into blood. The unique mirror-image configuration of this agent renders it resistant to hydrolysis and does not hybridize with native nucleic acids. Furthermore, this agent does not induce the innate immune response and has shown a favorable immunogenicity profile.

1 2D Structure

Emapticap pegol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-[[2-[[2-(2-methoxyethoxy)acetyl]-[2-(2-methoxyethoxy)ethyl]amino]acetyl]amino]hexyl dihydrogen phosphate

2.1.2 InChI

InChI=1S/C18H37N2O10P/c1-26-11-13-28-10-8-20(18(22)16-29-14-12-27-2)15-17(21)19-7-5-3-4-6-9-30-31(23,24)25/h3-16H2,1-2H3,(H,19,21)(H2,23,24,25)

2.1.3 InChI Key

QJAGBAPUFWBVSD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COCCOCCN(CC(=O)NCCCCCCOP(=O)(O)O)C(=O)COCCOC

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Nox-h94

2.2.2 Depositor-Supplied Synonyms

1. Emapticap Pegol

2. Olaptesed Pegol

3. Nox-a12 Free Acid

4. Nox-e36 Free Acid

5. Emapticap Pegol [inn]

6. Olaptesed Pegol [inn]

7. Lexaptepid Pegol [inn]

8. Unii-7x623i7ciy

9. Unii-ctl75x0v60

10. Unii-mtm792b442

11. 7x623i7ciy

12. Ctl75x0v60

13. Mtm792b442

14. 1390628-22-4

15. 1390630-22-4

16. 1390631-57-8

2.3 Create Date

2014-11-22

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₃₇N₂O₁₀P
Molecular Weight	472.5 g/mol
XLogP3	-1.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	21
Exact Mass	472.21858238 g/mol
Monoisotopic Mass	472.21858238 g/mol
Topological Polar Surface Area	153 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	518
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