(S)-2-((S)-2-((S)-2-aminopropanamido)-3-(4-(phosphonooxy)phenyl)propanamido)-4-methylpentanoic acid

ID: ALA5280162

Max Phase: Preclinical

Molecular Formula: C18H28N3O8P

Molecular Weight: 445.41

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](Cc1ccc(OP(=O)(O)O)cc1)NC(=O)[C@H](C)N)C(=O)O

Standard InChI:  InChI=1S/C18H28N3O8P/c1-10(2)8-15(18(24)25)21-17(23)14(20-16(22)11(3)19)9-12-4-6-13(7-5-12)29-30(26,27)28/h4-7,10-11,14-15H,8-9,19H2,1-3H3,(H,20,22)(H,21,23)(H,24,25)(H2,26,27,28)/t11-,14-,15-/m0/s1

Standard InChI Key:  LARVRBUOAJXJKI-CQDKDKBSSA-N

Molfile:  

 
     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
    3.2592   -2.7045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4621   -2.4917    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.6764   -3.2883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8279    0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124    1.2226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8279   -0.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3967    0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3187    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0345    0.8094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3187    2.0489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4655    0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    2.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4655    2.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4655    3.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812    2.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4655   -0.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812    1.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3967   -0.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3187   -0.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143   -1.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -1.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7457   -1.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430   -0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0276   -0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618   -1.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478   -2.9099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5436    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5436    2.0489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2592    0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  1
 13 14  1  0
 14 15  1  0
 14 16  1  0
 12 17  2  0
 12 18  1  0
  7 19  1  6
 19 20  1  0
 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  2  1  0
  2 27  2  0
  4 28  1  0
 28 29  1  6
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5280162

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 445.41

Molecular Weight (Monoisotopic): 445.1614

AlogP: 0.15

#Rotatable Bonds: 11

Polar Surface Area: 188.28

Molecular Species: ACID

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.78

CX Basic pKa: 8.09

CX LogP: -0.82

CX LogD: -4.88

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: 0.29

References

1. Huang Q, Zhong Y, Dong H, Zheng Q, Shi S, Zhu K, Qu X, Hu W, Zhang X, Wang Y..  (2020)  Revisiting signal transducer and activator of transcription 3 (STAT3) as an anticancer target and its inhibitor discovery: Where are we and where should we go?,  187  [PMID:31810784] [10.1016/j.ejmech.2019.111922]

Source

Source(1):

• Scientific Literature