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ACTIVE PHARMA INGREDIENTS

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Also known as: 170851-70-4, Ipamorelin [inn], Y9m3s784z6, Aib-his-d-2-nal-d-phe-lys-nh2, Nnc-260161, Nnc 26-0161

Molecular Formula

C₃₈H₄₉N₉O₅

Molecular Weight

711.9 g/mol

InChI Key

NEHWBYHLYZGBNO-BVEPWEIPSA-N

FDA UNII

Y9M3S784Z6

Ipamorelin is a pentapeptide (Aib-His-D-2-Nal-D-Phe-Lys-NH2) and a ghrelin mimetic with growth hormone (GH) releasing activity. Ipamorelin mimics ghrelin and binds to the ghrelin receptor (or GH secretagogue receptor, GHSR) in the brain, thereby selectively stimulating the release of GH from the pituitary gland. This results in increased plasma GH levels, which would affect many biological processes. Besides its presence in the brain, GHSR can also be found in the gastrointestinal tract, heart, lung, liver, kidney, pancreas, adipose tissue and immune cells. Unlike other GH releasing peptides, ipamorelin only stimulates GH release in a manner very similar to that of growth hormone releasing hormone.

1 2D Structure

Ipamorelin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-6-amino-2-[[(2R)-2-[[(2R)-2-[[(2S)-2-[(2-amino-2-methylpropanoyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-naphthalen-2-ylpropanoyl]amino]-3-phenylpropanoyl]amino]hexanamide

2.1.2 InChI

InChI=1S/C38H49N9O5/c1-38(2,41)37(52)47-32(21-28-22-42-23-43-28)36(51)46-31(20-25-15-16-26-12-6-7-13-27(26)18-25)35(50)45-30(19-24-10-4-3-5-11-24)34(49)44-29(33(40)48)14-8-9-17-39/h3-7,10-13,15-16,18,22-23,29-32H,8-9,14,17,19-21,39,41H2,1-2H3,(H2,40,48)(H,42,43)(H,44,49)(H,45,50)(H,46,51)(H,47,52)/t29-,30+,31+,32-/m0/s1

2.1.3 InChI Key

NEHWBYHLYZGBNO-BVEPWEIPSA-N

2.1.4 Canonical SMILES

CC(C)(C(=O)NC(CC1=CN=CN1)C(=O)NC(CC2=CC3=CC=CC=C3C=C2)C(=O)NC(CC4=CC=CC=C4)C(=O)NC(CCCCN)C(=O)N)N

2.1.5 Isomeric SMILES

CC(C)(C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@H](CC2=CC3=CC=CC=C3C=C2)C(=O)N[C@H](CC4=CC=CC=C4)C(=O)N[C@@H](CCCCN)C(=O)N)N

2.2 Other Identifiers

2.2.1 UNII

Y9M3S784Z6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aib-his-2nal-phe-lys-nh2

2.3.2 Depositor-Supplied Synonyms

1. 170851-70-4

2. Ipamorelin [inn]

3. Y9m3s784z6

4. Aib-his-d-2-nal-d-phe-lys-nh2

5. Nnc-260161

6. Nnc 26-0161

7. Nnc-26-0161

8. 2-methylalanyl-l-histidyl-3-(2-naphthyl)-d-alanyl-d-phenylalanyl-l-lysinamide

9. Ipamorelin Acetate

10. Unii-y9m3s784z6

11. Ipamorelin [who-dd]

12. Aib-his-2nal-phe-lys-nh2

13. Chembl58547

14. Schembl183305

15. Schembl8169698

16. Amy25371

17. Vga85170

18. Zinc29562299

19. Db12370

20. Ncgc00167295-01

21. As-56185

22. 2-methylalanyl-l-histidyl-3-(2-naphthyl)-d-alanyl-d-phenylalanyl-l-lysinamide.

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₈H₄₉N₉O₅
Molecular Weight	711.9 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	19
Exact Mass	711.38566570 g/mol
Monoisotopic Mass	711.38566570 g/mol
Topological Polar Surface Area	240 Å²
Heavy Atom Count	52
Formal Charge	0
Complexity	1200
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1