1-[(2R,15R)-2-(1-Amino-4-fluoro-isoquinolin-6-ylamino)-4,15,17-trimethyl-3,12-dioxo-13-oxa-4,11-diaza-tricyclo[14.2.2.1(6,10)]henicosa-1(19),6,8,10(21),16(20),17-hexaen-7-yl]-cyclopentanecarboxylic acid

ID: ALA3984725

PubChem CID: 134156593

Max Phase: Preclinical

Molecular Formula: C36H38FN5O5

Molecular Weight: 639.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2ccc1[C@@H](C)COC(=O)Nc1ccc(C3(C(=O)O)CCCC3)c(c1)CN(C)C(=O)[C@@H]2Nc1ccc2c(N)ncc(F)c2c1

Standard InChI:  InChI=1S/C36H38FN5O5/c1-20-14-22-6-9-26(20)21(2)19-47-35(46)41-24-8-11-29(36(34(44)45)12-4-5-13-36)23(15-24)18-42(3)33(43)31(22)40-25-7-10-27-28(16-25)30(37)17-39-32(27)38/h6-11,14-17,21,31,40H,4-5,12-13,18-19H2,1-3H3,(H2,38,39)(H,41,46)(H,44,45)/t21-,31+/m0/s1

Standard InChI Key:  AFGGMWNLRYRQDA-JCOAXYOVSA-N

Molfile:  

     RDKit          2D

 47 52  0  0  0  0  0  0  0  0999 V2000
    8.2464  -19.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5366  -19.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9285  -19.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2627  -20.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0771  -20.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875  -18.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2972  -18.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943  -17.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5857  -17.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8795  -18.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8817  -17.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758  -17.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4671  -17.5740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4688  -18.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753  -18.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1771  -16.3492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055  -18.8002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7126  -18.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209  -18.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113  -17.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4185  -17.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4176  -16.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7087  -15.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9993  -16.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037  -17.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7063  -15.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856  -14.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5208  -15.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4222  -19.6152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1280  -18.3883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8363  -18.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5434  -18.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2489  -18.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9555  -18.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9547  -17.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2413  -17.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5377  -17.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2372  -16.3422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274  -15.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8218  -16.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285  -14.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1267  -17.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1766  -19.6174    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895  -15.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9632  -20.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9701  -20.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6730  -19.5999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
 10  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 11  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 10  2  0
 12 16  1  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  6
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 19 29  2  0
 19 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 32  1  0
 36 38  1  0
 38 39  1  0
 39 28  1  0
 39 40  2  0
 26 41  1  1
 30 42  1  0
 15 43  1  0
 24 44  1  0
 33  1  1  0
  1 45  1  0
 45 46  1  0
 45 47  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3984725

   ---

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: 639.73

Molecular Weight (Monoisotopic): 639.2857

AlogP: 6.64

#Rotatable Bonds: 4

Polar Surface Area: 146.88

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.82

CX Basic pKa: 7.53

CX LogP: 4.13

CX LogD: 3.89

Aromatic Rings: 4

Heavy Atoms: 47

QED Weighted: 0.19

Np Likeness Score: 0.19

References

1. Ladziata VU, Glunz PW, Zou Y, Zhang X, Jiang W, Jacutin-Porte S, Cheney DL, Wei A, Luettgen JM, Harper TM, Wong PC, Seiffert D, Wexler RR, Priestley ES..  (2016)  Synthesis and P1' SAR exploration of potent macrocyclic tissue factor-factor VIIa inhibitors.,  26  (20): [PMID:27612545] [10.1016/j.bmcl.2016.08.088]

Source

Source(1):

• Scientific Literature