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Technical details about Enkephalin, Methionine, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. 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

2D Structure

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 Weight 573.7 g/mol
Molecular Formula C27H35N5O7S
XLogP3-2.1
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count9
Rotatable Bond Count16
Exact Mass573.22571965 g/mol
Monoisotopic Mass573.22571965 g/mol
Topological Polar Surface Area225 Ų
Heavy Atom Count40
Formal Charge0
Complexity847
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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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