PO3 2-Ile-Trp-O-3K

ID: ALA281785

PubChem CID: 44458259

Max Phase: Preclinical

Molecular Formula: C17H21K3N3O6P

Molecular Weight: 397.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](C)[C@H](NP(=O)([O-])[O-])C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)[O-].[K+].[K+].[K+]

Standard InChI:  InChI=1S/C17H24N3O6P.3K/c1-3-10(2)15(20-27(24,25)26)16(21)19-14(17(22)23)8-11-9-18-13-7-5-4-6-12(11)13;;;/h4-7,9-10,14-15,18H,3,8H2,1-2H3,(H,19,21)(H,22,23)(H3,20,24,25,26);;;/q;3*+1/p-3/t10-,14+,15+;;;/m1.../s1

Standard InChI Key:  YNPAVWJIUDXSQV-FDXGCDPUSA-K

Molfile:  

     RDKit          2D

 30 28  0  0  0  0  0  0  0  0999 V2000
    2.2042   -3.6792    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
    3.9542   -1.2875    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -0.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -0.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -3.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0292   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3667   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -1.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -2.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -1.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -1.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -0.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167    0.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667    0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1917   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792    2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3292   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6750   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    0.4458    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
    1.4292   -1.6042    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
  3  4  1  0
  4  6  1  1
  5 13  1  0
  6  2  1  0
  7  3  1  0
  8  9  1  0
  9  5  2  0
 10  7  1  6
 11 10  1  0
 12  5  1  0
 10 13  1  0
 14 12  2  0
 15  2  1  0
 16  2  1  0
 17  2  2  0
 18  3  2  0
 19 11  1  0
 20 11  2  0
  4 21  1  0
 22 12  1  0
 23 14  1  0
 24 21  1  0
 21 25  1  6
 26 24  1  0
 27 22  2  0
 28 27  1  0
 14  8  1  0
 28 23  2  0
M  CHG  6   1   1  15  -1  16  -1  19  -1  29   1  30   1
M  END

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: 397.37

Molecular Weight (Monoisotopic): 397.1403

AlogP: 1.38

#Rotatable Bonds: 9

Polar Surface Area: 151.75

Molecular Species: ACID

HBA: 3

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.84

CX Basic pKa: ┄

CX LogP: 1.23

CX LogD: -5.10

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.35

Np Likeness Score: 0.28

References

1. Fukami T, Hayama T, Amano Y, Nakamura Y, Arai Y, Matsuyama K, Yano M, Ishikawa K.  (1994)  Aminophosphonate endothelin converting enzyme inhibitors: potency-enhancing and selectivity-improving modifications of phosphoramidon,  4  (10): [10.1016/S0960-894X(01)80341-3]

Source

Source(1):

• Scientific Literature