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D-Methionine, N-[N-[N-(N-L-tyrosylglycyl)glycyl]-L-phenylalanyl]-

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Chemistry

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Also known as: Lupex, Chembl214392, Enkephalin, methionine, (2s,5s,14s)-14-amino-5-benzyl-15-(4-hydroxyphenyl)-2-(2-(methylthio)ethyl)-4,7,10,13-tetraoxo-3,6,9,12-tetraazapentadecan-1-oic acid, Opioid growth factor (ogf), Chebi:6618

Molecular Formula

C₂₇H₃₅N₅O₇S

Molecular Weight

573.7 g/mol

InChI Key

YFGBQHOOROIVKG-UHFFFAOYSA-N

One of the endogenous pentapeptides with morphine-like activity. It differs from LEU-ENKEPHALIN by the amino acid METHIONINE in position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.

1 2D Structure

Enkephalin, Methionine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[[2-[[2-[[2-[[2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid

2.1.2 InChI

InChI=1S/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)

2.1.3 InChI Key

YFGBQHOOROIVKG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CSCCC(C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 5 Methionine Enkephalin

2. 5-methionine Enkephalin

3. Enkephalin, 5-methionine

4. Enkephalin, Methionine

5. Met Enkephalin

6. Met(5)-enkephalin

7. Met-enkephalin

8. Methionine Enkephalin

2.2.2 Depositor-Supplied Synonyms

1. Lupex

2. Chembl214392

3. Enkephalin, Methionine

4. (2s,5s,14s)-14-amino-5-benzyl-15-(4-hydroxyphenyl)-2-(2-(methylthio)ethyl)-4,7,10,13-tetraoxo-3,6,9,12-tetraazapentadecan-1-oic Acid

5. Opioid Growth Factor (ogf)

6. Chebi:6618

7. Metencefalina

8. Metenkefaline

9. Metenkefalinum

10. Nsc-374896

11. 2-[[2-[[2-[[2-[[2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic Acid

12. Methionine-enkephalin

13. Methionine_enkephalin

14. Menk

15. [met(5)]enkephalin

16. [met(5)]-enkephalin

17. M-enk

18. L-tyrosylglycylglycyl-l-phenylalanyl-l-methionine

19. L-tyr-gly-gly-l-phe-l-met

20. Schembl1880497

21. Dtxsid90974125

22. Bcp25058

23. Bdbm50189255

24. H-l-tyr-gly-gly-l-phe-l-met-oh

25. Nsc374896

26. Nci60_008880

27. Ft-0770482

28. L024015

29. (met5)-enkephalin; Ccris 4225; Tyr-gly-gly-phe-met-oh; Methionine Enkephalin;h-tyr-gly-gly-phe-met-oh

30. 2-(2-(2-(2-(2-amino-3-(4-hydroxyphenyl)propanamido)acetamido)acetamido)-3-phenylpropanamido)-4-(methylthio)butanoic Acid

31. N-[2-({2-[(2-{[2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-3-phenylpropylidene]methionine

2.3 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₅N₅O₇S
Molecular Weight	573.7 g/mol
XLogP3	-2.1
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	16
Exact Mass	573.22571965 g/mol
Monoisotopic Mass	573.22571965 g/mol
Topological Polar Surface Area	225 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	847
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	3
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Neurotransmitter Agents

Substances used for their pharmacological actions on any aspect of neurotransmitter systems. Neurotransmitter agents include agonists, antagonists, degradation inhibitors, uptake inhibitors, depleters, precursors, and modulators of receptor function. (See all compounds classified as Neurotransmitter Agents.)

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