(S)-2-(6-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]-pyrimidin-6-yl)hexanamido)pentanedioic Acid

ID: ALA3086864

PubChem CID: 136240255

Max Phase: Preclinical

Molecular Formula: C17H23N5O6

Molecular Weight: 393.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(CCCCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C17H23N5O6/c18-17-21-14-10(15(26)22-17)8-9(19-14)4-2-1-3-5-12(23)20-11(16(27)28)6-7-13(24)25/h8,11H,1-7H2,(H,20,23)(H,24,25)(H,27,28)(H4,18,19,21,22,26)/t11-/m0/s1

Standard InChI Key:  DSEZCYKANVEUMR-NSHDSACASA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    2.9248  -18.9357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9236  -19.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317  -20.1642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299  -18.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3385  -18.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3433  -19.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233  -19.9991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6007  -19.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156  -18.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2156  -20.1633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6275  -17.7096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4179  -19.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8223  -18.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6395  -18.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0439  -17.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8611  -17.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2655  -17.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0827  -17.1844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8527  -16.4840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4871  -16.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3043  -16.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0743  -15.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2572  -15.7739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4787  -15.0590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7170  -17.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5342  -17.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9470  -17.8753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9386  -16.4599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
  4 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 20 18  1  6
 20 21  1  0
 20 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3086864

   ---

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: 393.40

Molecular Weight (Monoisotopic): 393.1648

AlogP: 0.37

#Rotatable Bonds: 11

Polar Surface Area: 191.26

Molecular Species: ACID

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.64

CX Basic pKa: 4.98

CX LogP: -1.05

CX LogD: -6.00

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.29

Np Likeness Score: 0.30

References

1. Wang Y, Cherian C, Orr S, Mitchell-Ryan S, Hou Z, Raghavan S, Matherly LH, Gangjee A..  (2013)  Tumor-targeting with novel non-benzoyl 6-substituted straight chain pyrrolo[2,3-d]pyrimidine antifolates via cellular uptake by folate receptor α and inhibition of de novo purine nucleotide biosynthesis.,  56  (21): [PMID:24111942] [10.1021/jm401139z]

Source

Source(1):

• Scientific Literature