3-Methoxy-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl]-benzamide

ID: ALA1084617

Cas Number: 887936-68-7

PubChem CID: 11604525

Product Number: T726144, Order Now?

Max Phase: Phase

Molecular Formula: C24H28N4O4

Molecular Weight: 436.51

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Apd791 | Temanogrel | APD-791 | APD791 | TEMANOGREL|887936-68-7|APD791|Temanogrel [USAN:INN]|UNII-F42Z27575A|APD 791|APD-791|Benzamide, 3-methoxy-N-[3-(1-methyl-1H-pyrazol-5-yl)-4-[2-(4-morpholinyl)ethoxy]phenyl]-|F42Z27575A|CHEMBL1084617|3-Methoxy-N-(3-(1-methyl-1H-pyrazol-5-yl)-4-(2-(morpholin-4- yl)ethoxy)phenyl)benzamide|3-Methoxy-N-(3-(2-methyl-2H-pyrazol-3-yl)-4-(2-morpholin-4-yl-ethoxy)-phenyl)- benzamide|3-methoxy-N-[3-(2-methylpyrazol-3-yl)-4-(2-morpholin-4-ylethoxy)phenyl]benzamide|BenShow More⌵

Synonyms from Alternative Forms(3): Temanogrel hcl | APD791 | Temanogrel hydrochloride

Canonical SMILES:  COc1cccc(C(=O)Nc2ccc(OCCN3CCOCC3)c(-c3ccnn3C)c2)c1

Standard InChI:  InChI=1S/C24H28N4O4/c1-27-22(8-9-25-27)21-17-19(26-24(29)18-4-3-5-20(16-18)30-2)6-7-23(21)32-15-12-28-10-13-31-14-11-28/h3-9,16-17H,10-15H2,1-2H3,(H,26,29)

Standard InChI Key:  ZEOQUKRCASTCFR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
  -11.2173    0.3992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0019    0.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3997    0.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6150    0.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1735   -0.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9581   -0.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5712   -0.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1296   -1.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5165   -2.2767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9142   -1.9796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0858   -2.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8704   -3.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4727   -3.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6442   -4.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4288   -4.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0419   -3.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.8265   -4.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.1614   -4.1034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -16.4940   -3.6185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0815   -4.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9065   -4.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.4940   -2.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6004   -5.2075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3850   -5.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5565   -6.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.3411   -6.5243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -17.7388   -6.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9542   -5.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5127   -7.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.2973   -7.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.9104   -7.0342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0458    1.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  4  2  2  0
  2  5  1  0
  3  4  1  0
  3  7  2  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 12 11  2  0
 11 13  1  0
 12 16  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 19 17  1  0
 17 20  2  0
 18 19  1  0
 18 21  2  0
 20 21  1  0
 19 22  1  0
 15 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 28 26  1  0
 26 29  1  0
 27 28  1  0
 27 31  1  0
 29 30  1  0
 30 31  1  0
  1 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1084617

   Temanogrel

2. Alternative Forms:

   

   ALA1084617

   TEMANOGREL HYDROCHLORIDE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 436.51

Molecular Weight (Monoisotopic): 436.2111

AlogP: 3.06

#Rotatable Bonds: 8

Polar Surface Area: 77.85

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.76

CX LogP: 2.55

CX LogD: 2.46

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.58

Np Likeness Score: -1.86

References

1. Xiong Y, Teegarden BR, Choi JS, Strah-Pleynet S, Decaire M, Jayakumar H, Dosa PI, Casper MD, Pham L, Feichtinger K, Ullman B, Adams J, Yuskin D, Frazer J, Morgan M, Sadeque A, Chen W, Webb RR, Connolly DT, Semple G, Al-Shamma H..  (2010)  Discovery and structure-activity relationship of 3-methoxy-N-(3-(1-methyl-1H-pyrazol-5-yl)-4-(2-morpholinoethoxy)phenyl)benzamide (APD791): a highly selective 5-hydroxytryptamine2A receptor inverse agonist for the treatment of arterial thrombosis.,  53  (11): [PMID:20455563] [10.1021/jm100044a]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names