(2S)-2-[[(2S)-2-[[(2R)-1-[[5-(dimethylamino)-1-naphthyl]sulfonyl]pyrrolidine-2-carbonyl]amino]-4-phenyl-butanoyl]amino]-5-guanidino-pentanoic acid

ID: ALA4644027

PubChem CID: 156018923

Max Phase: Preclinical

Molecular Formula: C33H43N7O6S

Molecular Weight: 665.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)c1cccc2c(S(=O)(=O)N3CCC[C@@H]3C(=O)N[C@@H](CCc3ccccc3)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)cccc12

Standard InChI:  InChI=1S/C33H43N7O6S/c1-39(2)27-15-6-13-24-23(27)12-7-17-29(24)47(45,46)40-21-9-16-28(40)31(42)37-25(19-18-22-10-4-3-5-11-22)30(41)38-26(32(43)44)14-8-20-36-33(34)35/h3-7,10-13,15,17,25-26,28H,8-9,14,16,18-21H2,1-2H3,(H,37,42)(H,38,41)(H,43,44)(H4,34,35,36)/t25-,26-,28+/m0/s1

Standard InChI Key:  KSPUMTJNNKKZAY-UNCTUWKVSA-N

Molfile:  

 
     RDKit          2D

 47 50  0  0  0  0  0  0  0  0999 V2000
   31.8966  -10.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6046   -9.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3129  -10.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3129  -11.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6072  -11.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8966  -11.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6072  -12.4431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3152  -12.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8991  -12.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0254  -11.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7293  -11.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7267  -10.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0182   -9.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0182   -9.1688    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.3102   -8.7612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5635   -9.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0160   -8.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4234   -7.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2251   -7.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8893   -7.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8078   -6.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5973   -7.8738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3054   -7.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0176   -7.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7257   -7.4662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4337   -7.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1418   -7.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8540   -7.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1418   -6.6467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4337   -8.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1418   -9.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1418   -9.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8540  -10.3322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5621   -9.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2701  -10.3322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5621   -9.1051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0176   -8.6933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3054   -6.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5973   -6.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5973   -5.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8894   -5.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8904   -4.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5988   -3.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3071   -4.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3097   -5.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8399   -9.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4300   -8.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 15 19  1  0
 19 20  1  6
 20 21  2  0
 20 22  1  0
 23 22  1  1
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 26 30  1  6
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 24 37  2  0
 23 38  1  0
 38 39  1  0
 39 40  1  0
 41 40  2  0
 42 41  1  0
 43 42  2  0
 44 43  1  0
 45 44  2  0
 40 45  1  0
 14 46  2  0
 14 47  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4644027

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 665.82

Molecular Weight (Monoisotopic): 665.2996

AlogP: 2.01

#Rotatable Bonds: 15

Polar Surface Area: 198.02

Molecular Species: ZWITTERION

HBA: 7

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.64

CX Basic pKa: 11.80

CX LogP: 0.69

CX LogD: 0.69

Aromatic Rings: 3

Heavy Atoms: 47

QED Weighted: 0.08

Np Likeness Score: -0.59

References

1. de la Sierra-Gallay IL, Belnou M, Chambraud B, Genet M, van Tilbeurgh H, Aumont-Nicaise M, Desmadril M, Baulieu EE, Jacquot Y, Byrne C..  (2020)  Bioinspired Hybrid Fluorescent Ligands for the FK1 Domain of FKBP52.,  63  (18): [PMID:32866001] [10.1021/acs.jmedchem.0c00825]

Source

Source(1):

• Scientific Literature