Mesulergine

ID: ALA12314

Max Phase: Phase

Molecular Formula: C18H26N4O2S

Molecular Weight: 362.50

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Synonyms from Alternative Forms(1): Mesulergine HCl

Canonical SMILES:  CN1C[C@@H](NS(=O)(=O)N(C)C)C[C@@H]2c3cccc4c3c(cn4C)C[C@H]21

Standard InChI:  InChI=1S/C18H26N4O2S/c1-20(2)25(23,24)19-13-9-15-14-6-5-7-16-18(14)12(10-21(16)3)8-17(15)22(4)11-13/h5-7,10,13,15,17,19H,8-9,11H2,1-4H3/t13-,15+,17+/m0/s1

Standard InChI Key:  JLVHTNZNKOSCNB-YSVLISHTSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
    1.1375    2.2708    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -3.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542   -0.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792    1.8208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875    2.7208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    1.5083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917    3.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6583   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750    3.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542    2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    0.1000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -1.3125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
  3  5  1  0
  4 16  1  0
  5  4  1  0
  6 10  1  0
  7  4  1  0
  8 15  1  0
  9  2  2  0
 10  3  2  0
 11  7  1  0
 12  1  1  0
 13 12  1  6
 14  1  1  0
 15 13  1  0
 16 13  1  0
 17  1  2  0
 18  1  2  0
 19  5  2  0
 20  6  1  0
 21  8  1  0
 22 23  2  0
 23 19  1  0
 24 14  1  0
 25 14  1  0
  4 26  1  6
  7 27  1  1
  8  7  1  0
  3  2  1  0
  9  6  1  0
 10 22  1  0
M  END

Alternative Forms

  1. Parent:

    ALA12314

    MESULERGINE
  2. Alternative Forms:

Associated Targets(Human)

HTR7 Tclin Serotonin 7 (5-HT7) receptor (5576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR6 Tchem Serotonin 6 (5-HT6) receptor (9749 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Htr2c Serotonin 2c (5-HT2c) receptor (1134 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr1b Serotonin 1 (5-HT1) receptor (408 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr1a Serotonin 1a (5-HT1a) receptor (8655 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr1b Serotonin 1b (5-HT1b) receptor (2343 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2b Serotonin 2 (5-HT2) receptor (2078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr7 Serotonin 7 (5-HT7) receptor (811 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr3a Serotonin 3 (5-HT3) receptor (1834 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 362.50Molecular Weight (Monoisotopic): 362.1776AlogP: 1.29#Rotatable Bonds: 3
Polar Surface Area: 57.58Molecular Species: NEUTRALHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 11.08CX Basic pKa: 6.88CX LogP: 1.08CX LogD: 0.97
Aromatic Rings: 2Heavy Atoms: 25QED Weighted: 0.90Np Likeness Score: 0.09

References

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11. Minetti P, Tinti MO, Carminati P, Castorina M, Di Cesare MA, Di Serio S, Gallo G, Ghirardi O, Giorgi F, Giorgi L, Piersanti G, Bartoccini F, Tarzia G..  (2005)  2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacological characterization.,  48  (22): [PMID:16250647] [10.1021/jm058018d]
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