Deltorphin I

Deltorphin I, also known as [D-Ala2]deltorphin I or deltorphin C, is a naturally occurring, exogenous opioid heptapeptide and hence, exorphin, with the amino acid sequence Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2.[1][2] While not known to be endogenous to humans or other mammals, deltorphin I, along with the other deltorphins and the dermorphins, is produced naturally in the skin of species of Phyllomedusa,[1] a genus of frogs native to South and Central America. Deltorphin possesses very high affinity and selectivity as an agonist for the δ-opioid receptor,[1][2] and on account of its unusually high blood-brain-barrier penetration rate,[3] produces centrally-mediated analgesic effects in animals even when administered peripherally.[4]

Deltorphin I
Names
IUPAC names
(3S)-3-[(2S)-2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-3-phenylpropanamido]-3-{[(1S)-1-{[(1S)-1-[(carbamoylmethyl)carbamoyl]-2-methylpropyl]carbamoyl}-2-methylpropyl]carbamoyl}propanoic acid
or
L-tyrosyl-D-alanyl-L-phenylalanyl-L-α-aspartyl-L-valyl-L-valylglycinamide
Other names
[D-Ala2]Deltorphin I; Deltorphin C
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
InChI
  • InChI=1S/C37H52N8O10/c1-19(2)30(36(54)40-18-28(39)47)45-37(55)31(20(3)4)44-35(53)27(17-29(48)49)43-34(52)26(16-22-9-7-6-8-10-22)42-32(50)21(5)41-33(51)25(38)15-23-11-13-24(46)14-12-23/h6-14,19-21,25-27,30-31,46H,15-18,38H2,1-5H3,(H2,39,47)(H,40,54)(H,41,51)(H,42,50)(H,43,52)(H,44,53)(H,45,55)(H,48,49)/t21-,25+,26+,27+,30+,31+/m1/s1
    Key: CJAORFIPPWIGPG-QXYJMILXSA-N
  • InChI=1/C37H52N8O10/c1-19(2)30(36(54)40-18-28(39)47)45-37(55)31(20(3)4)44-35(53)27(17-29(48)49)43-34(52)26(16-22-9-7-6-8-10-22)42-32(50)21(5)41-33(51)25(38)15-23-11-13-24(46)14-12-23/h6-14,19-21,25-27,30-31,46H,15-18,38H2,1-5H3,(H2,39,47)(H,40,54)(H,41,51)(H,42,50)(H,43,52)(H,44,53)(H,45,55)(H,48,49)/t21-,25+,26+,27+,30+,31+/m1/s1
    Key: CJAORFIPPWIGPG-QXYJMILXBS
SMILES
  • O=C(N)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)C)Cc2ccccc2)CC(=O)O)C(C)C)C(C)C
Properties
Chemical formula
 C37H52N8O10
Molar mass 768.856 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Erspamer V, Melchiorri P, Falconieri-Erspamer G, et al. (July 1989). "Deltorphins: a family of naturally occurring peptides with high affinity and selectivity for delta opioid binding sites". Proceedings of the National Academy of Sciences of the United States of America. 86 (13): 5188–92. Bibcode:1989PNAS...86.5188E. doi:10.1073/pnas.86.13.5188. PMC 297583. PMID 2544892.
  2. Balboni G, Marastoni M, Picone D, et al. (June 1990). "New features of the delta opioid receptor: conformational properties of deltorphin I analogues". Biochemical and Biophysical Research Communications. 169 (2): 617–22. doi:10.1016/0006-291X(90)90375-W. PMID 2162669.
  3. Fiori A, Cardelli P, Negri L, Savi MR, Strom R, Erspamer V (August 1997). "Deltorphin transport across the blood–brain barrier". Proceedings of the National Academy of Sciences of the United States of America. 94 (17): 9469–74. Bibcode:1997PNAS...94.9469F. doi:10.1073/pnas.94.17.9469. PMC 23226. PMID 9256506.
  4. Thomas SA, Abbruscato TJ, Hau VS, et al. (May 1997). "Structure-activity relationships of a series of [D-Ala2]deltorphin I and II analogues; in vitro blood–brain barrier permeability and stability". The Journal of Pharmacology and Experimental Therapeutics. 281 (2): 817–25. PMID 9152390.
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