(R)-N-((S)-2-(2-amino-2-oxoethyl)-3-oxo-2,3,4,5-tetrahydro-1H-naphtho[1,2-c]azepin-4-yl)-2-((S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanamido)-5-guanidinopentanamide

ID: ALA4161890

PubChem CID: 145960193

Max Phase: Preclinical

Molecular Formula: C33H42N8O5

Molecular Weight: 630.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)cc(C)c1C[C@H](N)C(=O)N[C@H](CCCNC(=N)N)C(=O)N[C@H]1Cc2ccc3ccccc3c2CN(CC(N)=O)C1=O

Standard InChI:  InChI=1S/C33H42N8O5/c1-18-12-22(42)13-19(2)24(18)15-26(34)30(44)39-27(8-5-11-38-33(36)37)31(45)40-28-14-21-10-9-20-6-3-4-7-23(20)25(21)16-41(32(28)46)17-29(35)43/h3-4,6-7,9-10,12-13,26-28,42H,5,8,11,14-17,34H2,1-2H3,(H2,35,43)(H,39,44)(H,40,45)(H4,36,37,38)/t26-,27+,28-/m0/s1

Standard InChI Key:  YIFWHJCELZDCAJ-IARZGTGTSA-N

Molfile:  

     RDKit          2D

 46 49  0  0  0  0  0  0  0  0999 V2000
   37.1151  -20.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8997  -20.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8740  -21.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6007  -20.8160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7458  -20.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5750  -21.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2827  -20.8838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8673  -20.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5750  -22.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9904  -21.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6981  -20.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4058  -21.2924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6981  -20.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9904  -22.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6981  -22.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6981  -23.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4058  -23.7439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4058  -24.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1135  -24.9697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6981  -24.9697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3813  -19.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2067  -19.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9103  -22.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2625  -21.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0086  -20.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6703  -21.4415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0929  -20.1492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8673  -20.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1596  -21.2924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1596  -19.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1626  -18.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4557  -18.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7470  -18.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7496  -19.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4571  -20.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4598  -20.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8711  -18.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0387  -18.4322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9322  -18.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3078  -17.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1312  -17.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5776  -18.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3981  -18.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7732  -17.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3218  -17.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5028  -17.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 21  1  0
  1  3  1  0
  3  4  1  0
 22  5  1  0
  4  5  1  0
  6  7  1  0
  6  8  1  0
  6  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 10 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 12  1  1
 21 22  2  0
 22 42  1  0
 41 40  1  0
 39 21  1  0
  3 23  2  0
  4 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
  8 28  1  1
  8 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 35 36  1  0
 31 37  1  0
 33 38  1  0
 39 40  2  0
 41 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 45 46  1  0
 46 41  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4161890

   ---

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: 630.75

Molecular Weight (Monoisotopic): 630.3278

AlogP: 0.34

#Rotatable Bonds: 12

Polar Surface Area: 229.75

Molecular Species: BASE

HBA: 7

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.74

CX Basic pKa: 11.79

CX LogP: 0.08

CX LogD: -2.21

Aromatic Rings: 3

Heavy Atoms: 46

QED Weighted: 0.08

Np Likeness Score: 0.24

References

1. Van der Poorten O, Van Den Hauwe R, Eiselt E, Betti C, Guillemyn K, Chung NN, Hallé F, Bihel F, Schiller PW, Tourwé D, Sarret P, Gendron L, Ballet S..  (2017)  χ-Space Screening of Dermorphin-Based Tetrapeptides through Use of Constrained Arylazepinone and Quinolinone Scaffolds.,  8  (11): [PMID:29152051] [10.1021/acsmedchemlett.7b00347]

Source

Source(1):

• Scientific Literature