Methyl 3-((R)-1-((R)-2-(4-cyclopropyl-1-oxo-1,2-dihydroisoquinolin-7-ylamino)-2-(3,4-dimethoxyphenyl)acetyl)pyrrolidin-2-yl)-4-(isopropylsulfonyl)phenylcarbamate

ID: ALA3982319

PubChem CID: 25002154

Max Phase: Preclinical

Molecular Formula: C37H42N4O8S

Molecular Weight: 702.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1ccc(S(=O)(=O)C(C)C)c([C@H]2CCCN2C(=O)[C@H](Nc2ccc3c(C4CC4)c[nH]c(=O)c3c2)c2ccc(OC)c(OC)c2)c1

Standard InChI:  InChI=1S/C37H42N4O8S/c1-21(2)50(45,46)33-15-12-25(40-37(44)49-5)19-28(33)30-7-6-16-41(30)36(43)34(23-10-14-31(47-3)32(17-23)48-4)39-24-11-13-26-27(18-24)35(42)38-20-29(26)22-8-9-22/h10-15,17-22,30,34,39H,6-9,16H2,1-5H3,(H,38,42)(H,40,44)/t30-,34-/m1/s1

Standard InChI Key:  CRBTZBQJUBHGJG-KAODMTDESA-N

Molfile:  

     RDKit          2D

 50 55  0  0  0  0  0  0  0  0999 V2000
    8.0765   -5.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -6.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -6.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0699   -7.2349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3569   -6.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3569   -6.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6534   -5.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9362   -5.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9362   -6.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2317   -7.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5121   -6.8266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5197   -6.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2287   -5.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2287   -4.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2317   -8.0509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6459   -7.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4898   -7.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4881   -8.0579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2032   -6.8264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9530   -7.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9513   -7.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6674   -8.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6653   -9.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9483   -9.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2370   -9.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2396   -8.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5236   -9.6177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5223  -10.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8131  -10.8453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8117  -11.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2328  -10.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3801   -7.9942    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.0844   -8.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0688   -9.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7976   -8.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0934   -7.5848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3965   -7.1732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5066   -6.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0973   -5.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2928   -6.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4982   -5.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4982   -4.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7891   -4.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7891   -3.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0811   -3.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0765   -4.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3653   -4.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6533   -4.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6348   -4.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8139   -4.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  8 13  1  0
 13 14  1  0
 10 15  2  0
 16  9  1  0
  5 16  2  0
 17  3  1  0
 17 18  2  0
 19 17  1  0
 19 20  1  0
 20 21  1  6
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 21 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 22 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 32 36  2  0
 32 37  2  0
 20 38  1  0
 38 39  1  0
 39 40  1  0
 40 19  1  0
 41  2  1  0
 42 41  2  0
 43 42  1  0
 43 44  1  0
 44 45  1  0
 46 43  2  0
  1 46  1  0
 46 47  1  0
 47 48  1  0
 49 14  1  0
 50 49  1  0
 14 50  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982319

   methyl N-[3-[(2R)-1-[(2R)-2-[(4-cyclopropyl-1-oxo-2H-isoquinolin-7-yl)amino]-2-(3,4-dimethoxyphenyl)acetyl]pyrrolidin-2-yl]-4-propan-2-ylsulfonylphenyl]carbamate

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 702.83

Molecular Weight (Monoisotopic): 702.2723

AlogP: 6.30

#Rotatable Bonds: 11

Polar Surface Area: 156.13

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.25

CX Basic pKa: 0.43

CX LogP: 4.07

CX LogD: 4.07

Aromatic Rings: 4

Heavy Atoms: 50

QED Weighted: 0.16

Np Likeness Score: -0.85

References

1. Wurtz NR, Parkhurst BL, Jiang W, DeLucca I, Zhang X, Ladziata V, Cheney DL, Bozarth JR, Rendina AR, Wei A, Luettgen JM, Wu Y, Wong PC, Seiffert DA, Wexler RR, Priestley ES..  (2016)  Discovery of Phenylglycine Lactams as Potent Neutral Factor VIIa Inhibitors.,  7  (12): [PMID:27994741] [10.1021/acsmedchemlett.6b00282]

Source

Source(1):

• Scientific Literature