Details of the Drug

General Information of Drug (ID: DMT2CZK)

Drug Name

Leucine-enkephalin

Synonyms

YGGFL; URLZCHNOLZSCCA-UHFFFAOYSA-N; 2-[[2-[[2-[[2-[[2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid; Spectrum_001429; AC1L1GYW; Spectrum5_000656; Spectrum4_001048; Spectrum2_001177; Spectrum3_001521; AC1Q1P3H; KBioSS_001909; KBioGR_001316; BSPBio_002902

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1], [2]

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 4

Molecular Weight (mw)

555.6

Topological Polar Surface Area (xlogp)

-2.3

Rotatable Bond Count (rotbonds)

15

Hydrogen Bond Donor Count (hbonddonor)

7

Hydrogen Bond Acceptor Count (hbondacc)

8

Chemical Identifiers

Formula: C28H37N5O7
IUPAC Name: (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
Canonical SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)N
InChI: InChI=1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1
InChIKey: URLZCHNOLZSCCA-VABKMULXSA-N

Cross-matching ID

PubChem CID: 461776
ChEBI ID: CHEBI:89656
CAS Number: 58822-25-6
TTD ID: D06EES

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Opioid receptor delta (OPRD1)	TT27RFC	OPRD_HUMAN	Agonist	[3]
Opioid receptor mu (MOP)	TTKWM86	OPRM_HUMAN	Inhibitor	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Opioid receptor mu (MOP)	DTT	OPRM1	5.94E-01	-0.02	-0.17
Opioid receptor delta (OPRD1)	DTT	OPRD1	5.52E-01	0.03	0.23

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1613).
2	Peptides as receptor selectivity modulators of opiate pharmacophores. J Med Chem. 1986 Jul;29(7):1222-5.
3	Inverse agonist action of Leu-enkephalin at delta(2)-opioid receptors mediates spinal antianalgesia. J Pharmacol Exp Ther. 2001 May;297(2):582-9.
4	Buprenorphine is a weak partial agonist that inhibits opioid receptor desensitization. J Neurosci. 2009 Jun 3;29(22):7341-8.
5	Antianalgesia: stereoselective action of dextro-morphine over levo-morphine on glia in the mouse spinal cord.J Pharmacol Exp Ther.2005 Sep;314(3):1101-8.
6	Clinical pipeline report, company report or official report of signaturerx.
7	2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
8	The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
9	Concentration-effect relationship of intravenous alfentanil and ketamine on peripheral neurosensory thresholds, allodynia and hyperalgesia of neuropathic pain. Pain. 2001 Mar;91(1-2):177-87.
10	2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
11	Molecular characterization of eluxadoline as a potential ligand targeting mu-delta opioid receptor heteromers.Biochem Pharmacol.2014 Dec 1;92(3):448-56.
12	Drug design and synthesis of a novel kappa opioid receptor agonist with an oxabicyclo[2.2.2]octane skeleton and its pharmacology. Bioorg Med Chem Lett. 2010 Jan 1;20(1):121-4.
13	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 319).
14	Butorphanol: effects of a prototypical agonist-antagonist analgesic on kappa-opioid receptors. J Pharmacol Sci. 2005 Jun;98(2):109-16.
15	Identification of opioid ligands possessing mixed micro agonist/delta antagonist activity among pyridomorphinans derived from naloxone, oxymorphone, and hydromorphone [correction of hydropmorphone]. J Med Chem. 2004 Mar 11;47(6):1400-12.
16	Loperamide: evidence of interaction with mu and delta opioid receptors. Life Sci. 1983;33 Suppl 1:315-8.
17	Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307.
18	Wax PM, Becker CE, Curry SC: Unexpected gas casualties in Moscow: a medical toxicology perspective. Ann Emerg Med. 2003 May;41(5):700-5.
19	Molecular Mechanisms of Opioid Receptor-Dependent Signaling and Behavior. Anesthesiology. 2011 December; 115(6): 1363-1381.
20	Delta-opioid receptor agonists inhibit neuromuscular transmission in human colon. Eur J Pharmacol. 1994 Sep 1;262(1-2):33-9.
21	Preclinical pharmacology of AZD2327: a highly selective agonist of the delta-opioid receptor. J Pharmacol Exp Ther. 2011 Jul;338(1):195-204.