(S)-2-({5-[3-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]-pyrimidin-6-yl)propyl]thiophene-2-carbonyl}-amino)-pentanoic Acid

ID: ALA3335607

PubChem CID: 136044174

Max Phase: Preclinical

Molecular Formula: C19H23N5O4S

Molecular Weight: 417.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@H](NC(=O)c1ccc(CCCc2cc3c(=O)[nH]c(N)nc3[nH]2)s1)C(=O)O

Standard InChI:  InChI=1S/C19H23N5O4S/c1-2-4-13(18(27)28)22-17(26)14-8-7-11(29-14)6-3-5-10-9-12-15(21-10)23-19(20)24-16(12)25/h7-9,13H,2-6H2,1H3,(H,22,26)(H,27,28)(H4,20,21,23,24,25)/t13-/m0/s1

Standard InChI Key:  VQICARSCVQQGJK-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   24.7175  -15.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6335  -14.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8862  -13.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2229  -14.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3069  -15.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4648  -15.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0542  -15.5423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2926  -13.7675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2086  -12.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4613  -12.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8677  -12.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8677  -11.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6450  -11.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1251  -12.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6450  -12.7275    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.9423  -12.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3509  -12.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1681  -12.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5620  -16.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8529  -15.5947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8529  -14.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5620  -14.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2669  -14.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2669  -15.5947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2464  -14.2297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3912  -13.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5767  -13.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9760  -14.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5620  -16.8205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  2  0
  1  7  1  0
  9 10  2  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 11 15  1  0
  9 11  1  0
 16 17  1  0
 17 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 19 24  1  0
 26 27  2  0
 25 27  1  0
 21 25  1  0
 22 26  1  0
 23 28  2  0
 19 29  1  0
 18 27  1  0
 14 16  1  0
  8  9  1  0
  2  8  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3335607

   ---

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: 417.49

Molecular Weight (Monoisotopic): 417.1471

AlogP: 2.05

#Rotatable Bonds: 9

Polar Surface Area: 153.96

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.01

CX Basic pKa: 4.75

CX LogP: 1.76

CX LogD: -0.43

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.36

Np Likeness Score: -0.55

References

1. Golani LK, George C, Zhao S, Raghavan S, Orr S, Wallace A, Wilson MR, Hou Z, Matherly LH, Gangjee A..  (2014)  Structure-activity profiles of novel 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolates with modified amino acids for cellular uptake by folate receptors α and β and the proton-coupled folate transporter.,  57  (19): [PMID:25234128] [10.1021/jm501113m]

Source

Source(1):

• Scientific Literature