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Chemistry

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Also known as: 81733-79-1, Tyr-d-ala-gly-phe-leu-arg, (2s)-2-[[(2s)-2-[[(2s)-2-[[2-[[(2r)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid, Tageflar, V13505565p, Enkephalin-leu, ala(2)-arg(6)-
Molecular Formula
C35H51N9O8
Molecular Weight
725.8  g/mol
InChI Key
GDPHPXYFLPDZGH-XBTMSFKCSA-N
FDA UNII
V13505565P

Dalargin
1 2D Structure

Dalargin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid
2.1.2 InChI
InChI=1S/C35H51N9O8/c1-20(2)16-27(32(49)43-26(34(51)52)10-7-15-39-35(37)38)44-33(50)28(18-22-8-5-4-6-9-22)42-29(46)19-40-30(47)21(3)41-31(48)25(36)17-23-11-13-24(45)14-12-23/h4-6,8-9,11-14,20-21,25-28,45H,7,10,15-19,36H2,1-3H3,(H,40,47)(H,41,48)(H,42,46)(H,43,49)(H,44,50)(H,51,52)(H4,37,38,39)/t21-,25+,26+,27+,28+/m1/s1
2.1.3 InChI Key
GDPHPXYFLPDZGH-XBTMSFKCSA-N
2.1.4 Canonical SMILES
CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)C(C)NC(=O)C(CC2=CC=C(C=C2)O)N
2.1.5 Isomeric SMILES
C[C@H](C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CC2=CC=C(C=C2)O)N
2.2 Other Identifiers
2.2.1 UNII
V13505565P
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-ala-6-arg-leu-enkephalin

2. Enkephalin, Ala(2)-leu(5)-arg(6)-

3. Enkephalin-leu, Ala(2)-arg(6)-

4. Enkephalin-leu, Ala(2)-arg(6)-, (d-arg-l-tyr-d-ala-l-phe-d-leu)-isomer

5. Enkephalin-leu, Ala(2)-arg(6)-, (d-arg-l-tyr-d-ala-l-phe-l-leu)-isomer

6. Enkephalin-leu, Ala(2)-arg(6)-, (l-arg-l-tyr-d-ala-l-phe-d-leu)-isomer

7. Enkephalin-leu, Alanyl(2)-arginine(6)-

8. Leu-enkephalin, Ala(2)-arg(6)-

9. Leucine-enkephalin, Ala(2)-arg(6)-

10. Tageflar

11. Tyr-ala-gly-phe-leu-arg

12. Tyrosyl-alanyl-glycyl-phenylalanyl--leucyl-arginine

2.3.2 Depositor-Supplied Synonyms

1. 81733-79-1

2. Tyr-d-ala-gly-phe-leu-arg

3. (2s)-2-[[(2s)-2-[[(2s)-2-[[2-[[(2r)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanoic Acid

4. Tageflar

5. V13505565p

6. Enkephalin-leu, Ala(2)-arg(6)-

7. (d-ala2)-leu-enkephalin-arg

8. Unii-v13505565p

9. (d-ala2)-leucine Enkephalin-arg

10. Dalargine

11. Brn 4287455

12. 2-d-alanine-1-6-beta-neoendorphin (human)

13. Dalargin [who-dd]

14. Tyrosyl-d-alanyl-glycyl-phenylalanyl-leucyl-arginine

15. Dtxsid50231302

16. 1-6-(d-ala2)-dynorphin

17. Ex-a5715

18. H-tyr-d-ala-gly-phe-leu-arg-oh

19. Zinc53255341

20. N(sup 2)-(n-(n-(n-(l-tyrosyl-d-alanyl)glycyl)-l-phenylalanyl)-l-leucyl)-l-arginine

21. 1-6-beta-neoendorphin (human), 2-d-alanine-

22. Q27291394

23. 1-6-.beta.-neoendorphin (human), 2-d-alanine-

24. L-arginine, L-tyrosyl-d-alanylglycyl-l-phenylalanyl-l-leucyl-

25. L-arginine, N(sup 2)-(n-(n-(n-(l-tyrosyl-d-alanyl)glycyl)-l-phenylalanyl)-l-leucyl)-

26. (2s,5s,8s,14r,17s)-17-amino-8-benzyl-2-(3-guanidinopropyl)-18-(4-hydroxyphenyl)-5-isobutyl-14-methyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazaoctadecan-1-oic Acid

2.4 Create Date
2006-07-28
3 Chemical and Physical Properties
Molecular Weight 725.8 g/mol
Molecular Formula C35H51N9O8
XLogP3-2.5
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count10
Rotatable Bond Count21
Exact Mass725.38605962 g/mol
Monoisotopic Mass725.38605962 g/mol
Topological Polar Surface Area293 Ų
Heavy Atom Count52
Formal Charge0
Complexity1210
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Adjuvants, Immunologic

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)


Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)


Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)


Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)


Anti-Ulcer Agents

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)


Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)


Gastrointestinal Agents

Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)


Sympatholytics

Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here. (See all compounds classified as Sympatholytics.)


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