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

ID: ALA3335604

PubChem CID: 136044176

Max Phase: Preclinical

Molecular Formula: C18H19N5O6S

Molecular Weight: 433.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(CCCc3ccc(C(=O)N[C@@H](CC(=O)O)C(=O)O)s3)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C18H19N5O6S/c19-18-22-14-10(15(26)23-18)6-8(20-14)2-1-3-9-4-5-12(30-9)16(27)21-11(17(28)29)7-13(24)25/h4-6,11H,1-3,7H2,(H,21,27)(H,24,25)(H,28,29)(H4,19,20,22,23,26)/t11-/m0/s1

Standard InChI Key:  VLHCBXFJXATDOK-NSHDSACASA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   21.6032  -12.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6872  -13.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4345  -13.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0937  -12.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8559  -11.9430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2623  -11.7932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0096  -12.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8410  -13.2724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0281  -13.5680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1121  -14.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8594  -14.7128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4530  -14.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4530  -15.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6716  -15.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1956  -15.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6716  -14.6080    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.3784  -15.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9698  -14.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1526  -14.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7587  -11.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4678  -11.7449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4678  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7587  -12.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0496  -12.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0496  -11.7449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0743  -13.1099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9295  -13.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7440  -13.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3447  -12.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7587  -10.5191    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
  1  5  2  0
  1  6  1  0
  4  7  2  0
  4  8  1  0
 10 11  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 12 16  1  0
 10 12  1  0
 17 18  1  0
 18 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 20 25  1  0
 27 28  2  0
 26 28  1  0
 22 26  1  0
 23 27  1  0
 24 29  2  0
 20 30  1  0
 19 28  1  0
 15 17  1  0
  9 10  1  0
  2  9  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3335604

   ---

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: 433.45

Molecular Weight (Monoisotopic): 433.1056

AlogP: 0.73

#Rotatable Bonds: 9

Polar Surface Area: 191.26

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.69

CX Basic pKa: 4.63

CX LogP: 0.08

CX LogD: -4.08

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: -0.42

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