SID50112921

ID: ALA1604571

Cas Number: 98626-50-7

PubChem CID: 2311

Max Phase: Preclinical

Molecular Formula: C24H28N2O5

Molecular Weight: 424.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(CCc1ccccc1)NC1CCc2ccccc2N(CC(=O)O)C1=O

Standard InChI:  InChI=1S/C24H28N2O5/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28)

Standard InChI Key:  XPCFTKFZXHTYIP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    2.4909    1.0270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089   -1.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089   -0.2462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239    3.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9170    3.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499    1.9383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589   -0.2462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3178    2.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3067    1.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7714    0.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0323    1.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5941    0.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1553    1.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3178    3.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    2.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7468    2.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7714   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0323    3.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7468    3.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1287    3.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5964   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7714   -2.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589   -3.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7714   -3.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -3.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8339   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589   -4.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -3.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -4.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464   -2.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0
  2 21  1  0
  2 27  1  0
  3 21  2  0
  4 20  2  0
  5 20  1  0
  6  8  1  0
  6  9  1  0
  6 15  1  0
  7 10  1  0
  7 17  1  0
  8 11  2  0
  8 14  1  0
  9 10  1  0
 10 12  1  0
 11 13  1  0
 11 16  1  0
 12 13  1  0
 14 18  2  0
 15 20  1  0
 16 19  2  0
 17 21  1  0
 17 22  1  0
 18 19  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 25 28  1  0
 26 29  2  0
 27 31  1  0
 28 30  2  0
 29 30  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1604571

   2-((S)-3-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)acetic acid

2. Parent:

   

   ALA1604571

   2-[3-[(1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino]-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 424.50

Molecular Weight (Monoisotopic): 424.1998

AlogP: 2.57

#Rotatable Bonds: 9

Polar Surface Area: 95.94

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.53

CX Basic pKa: 5.36

CX LogP: 1.54

CX LogD: 0.07

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -0.29

References

1. PubChem BioAssay data set, 

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

3. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

4. Zimmermann M, Zimmermann-Kogadeeva M, Wegmann R, Goodman AL..  (2019)  Mapping human microbiome drug metabolism by gut bacteria and their genes.,  570  (7762): [PMID:31158845] [10.1038/s41586-019-1291-3]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• AstraZeneca Deposited Data
• Zimmerman Lab Biotransformation data Dec 2023