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

ID: ALA3335605

PubChem CID: 136044173

Max Phase: Preclinical

Molecular Formula: C20H23N5O6S

Molecular Weight: 461.50

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H23N5O6S/c21-20-24-16-12(17(28)25-20)9-10(22-16)3-1-4-11-7-8-14(32-11)18(29)23-13(19(30)31)5-2-6-15(26)27/h7-9,13H,1-6H2,(H,23,29)(H,26,27)(H,30,31)(H4,21,22,24,25,28)/t13-/m0/s1

Standard InChI Key:  NDBHIBYSTUVPRS-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

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    6.2448  -14.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0761  -15.4440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3472  -16.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1733  -16.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4642  -15.6422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4642  -14.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1733  -14.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8823  -14.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8823  -15.6422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8577  -14.2813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0025  -13.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1921  -13.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5873  -14.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1733  -16.8680    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
  5  6  1  0
  1  7  2  0
  1  8  1  0
  6  9  2  0
  6 10  1  0
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 15 16  1  0
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 14 18  1  0
 12 14  1  0
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 20 21  1  0
 22 23  2  0
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 24 25  2  0
 25 26  1  0
 26 27  1  0
 22 27  1  0
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 28 30  1  0
 24 28  1  0
 25 29  1  0
 26 31  2  0
 22 32  1  0
 21 30  1  0
 17 19  1  0
 11 12  1  0
  2 11  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3335605

   ---

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: 461.50

Molecular Weight (Monoisotopic): 461.1369

AlogP: 1.51

#Rotatable Bonds: 11

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: 4.86

CX LogP: 0.74

CX LogD: -4.32

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.25

Np Likeness Score: -0.29

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