Details of the Drug

General Information of Drug (ID: DMSEIUP)

Drug Name
2-iodo-melatonin
Synonyms
2-Iodomelatonin; 93515-00-5; n-[2-(2-iodo-5-methoxy-1h-indol-3-yl)ethyl]acetamide; CHEMBL289233; N-(2-(2-Iodo-5-methoxy-1H-indol-3-yl)ethyl)acetamide; acetamide,n-[2-(2-iodo-5-methoxy-1h-indol-3-yl)ethyl]-; Acetamide, N-(2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl)-, (3beta)-; Acetamide, N-(2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl)-; SR-01000075935; 2-I-MLT; Melatonin,2-Iodo; ML2; Tocris-0737; Lopac-I-1899; AC1L3GZ8; AC1Q5P6Z; Lopac0_000610; SCHEMBL163451; GTPL1343; BDBM29611; CTK8F4316; DTXSID30239462; 2-iodomelatonin; IODOMELATONIN
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 358.17
Topological Polar Surface Area (xlogp) 2.3
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C13H15IN2O2
IUPAC Name
N-[2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Canonical SMILES
CC(=O)NCCC1=C(NC2=C1C=C(C=C2)OC)I
InChI
InChI=1S/C13H15IN2O2/c1-8(17)15-6-5-10-11-7-9(18-2)3-4-12(11)16-13(10)14/h3-4,7,16H,5-6H2,1-2H3,(H,15,17)
InChIKey
FJDDSMSDZHURBJ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
115348
ChEBI ID
CHEBI:109558
CAS Number
93515-00-5
DrugBank ID
DB08190
TTD ID
D0H6YF

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Melatonin receptor type 1A (MTNR1A) TT0WAIE MTR1A_HUMAN Agonist [3], [2]
Melatonin receptor type 1B (MTNR1B) TT32JK8 MTR1B_HUMAN Inhibitor [2]
Quinone reductase 2 (NQO2) TTJLP0R NQO2_HUMAN Inhibitor [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

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2 Synthesis of nitroindole derivatives with high affinity and selectivity for melatoninergic binding sites MT(3). J Med Chem. 2002 Apr 25;45(9):1853-9.
3 Characterization of a retinal melatonin receptor. J Pharmacol Exp Ther. 1985 Aug;234(2):395-401.
4 Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities. J Med Chem. 2009 Apr 9;52(7):1873-84.
5 MT1 and MT2 melatonin receptors: ligands, models, oligomers, and therapeutic potential. J Med Chem. 2014 Apr 24;57(8):3161-85.
6 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: 7393).
7 Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
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9 Design and synthesis of benzofuranic derivatives as new ligands at the melatonin-binding site MT3. Bioorg Med Chem. 2008 May 1;16(9):4954-62.
10 Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT(2)-selective melatonin ligands. Bioorg Med Chem Lett. 2010 Apr 15;20(8):2582-5.
11 Mapping the melatonin receptor. 7. Subtype selective ligands based on beta-substituted N-acyl-5-methoxytryptamines and beta-substituted N-acyl-5-me... J Med Chem. 2006 Jun 15;49(12):3509-19.
12 2-[(2,3-dihydro-1H-indol-1-yl)methyl]melatonin analogues: a novel class of MT2-selective melatonin receptor antagonists. J Med Chem. 2009 Feb 12;52(3):826-33.
13 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
14 Imidazoacridin-6-ones as novel inhibitors of the quinone oxidoreductase NQO2. Bioorg Med Chem Lett. 2010 May 1;20(9):2832-6.
15 CenterWatch. Drugs in Clinical Trials Database. CenterWatch. 2008.
16 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
17 Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer. Bioorg Med Chem. 2010 Jul 15;18(14):5352-66.
18 In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
19 The human MT1 melatonin receptor stimulates cAMP production in the human neuroblastoma cell line SH-SY5Y cells via a calcium-calmodulin signal transduction pathway. J Neuroendocrinol. 2005 Mar;17(3):170-8.
20 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: 288).
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24 Effects of two melatonin analogues, S-20098 and S-20928, on melatonin receptors in the pars tuberalis of the rat. J Pineal Res. 1998 Oct;25(3):172-6.
25 US patent application no. 5,151,446, Substituted 2-amidotetralins as melatonin agonists and antagonists.
26 Novel non-indolic melatonin receptor agonists differentially entrain endogenous melatonin rhythm and increase its amplitude. Eur J Pharmacol. 1999 Oct 15;382(3):157-66.