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

ID: ALA605580

PubChem CID: 135862924

Max Phase: Preclinical

Molecular Formula: C21H25N5O6S

Molecular Weight: 475.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(CCCCCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)s3)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C21H25N5O6S/c22-21-25-17-13(18(29)26-21)10-11(23-17)4-2-1-3-5-12-6-8-15(33-12)19(30)24-14(20(31)32)7-9-16(27)28/h6,8,10,14H,1-5,7,9H2,(H,24,30)(H,27,28)(H,31,32)(H4,22,23,25,26,29)/t14-/m0/s1

Standard InChI Key:  NDMAMOPJTVHRPP-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    1.6141   -4.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2908   -5.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091   -6.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6194   -5.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4404   -4.9426    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3343   -6.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3348   -6.9849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0484   -5.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496   -7.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502   -8.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7650   -8.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7657   -9.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7638   -6.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4786   -7.3957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631   -6.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0516   -9.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4804   -9.8707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216   -2.3328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071   -3.5749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071   -1.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3881   -2.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3835   -3.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921   -3.4158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076   -2.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5996   -2.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2826   -2.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661   -3.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0411   -3.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3753   -4.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083   -1.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361   -3.5749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002   -4.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  2  0
 12 17  1  0
 18 19  1  0
  3  4  2  0
  7  9  1  0
  4  5  1  0
  9 10  1  0
 18 21  1  0
 19 20  2  0
 20 23  1  0
 22 21  1  0
 22 23  2  0
  5  1  1  0
 10 11  1  0
 11 12  1  0
  4  6  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 22  1  0
  9 13  1  6
 25 27  1  0
  1  2  2  0
 27 28  1  0
 13 14  2  0
 28 29  1  0
  6  7  1  0
 29 30  1  0
 13 15  1  0
 21 31  2  0
  2  3  1  0
 19 32  1  0
 12 16  2  0
 30 33  1  0
 33  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA605580

   ---

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: 475.53

Molecular Weight (Monoisotopic): 475.1526

AlogP: 1.90

#Rotatable Bonds: 12

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: 3.64

CX Basic pKa: 4.97

CX LogP: 1.11

CX LogD: -3.88

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: -0.28

References

1. Wang L, Cherian C, Desmoulin SK, Polin L, Deng Y, Wu J, Hou Z, White K, Kushner J, Matherly LH, Gangjee A..  (2010)  Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier for cellular entry.,  53  (3): [PMID:20085328] [10.1021/jm9015729]

Source

Source(1):

• Scientific Literature