2-{4-[2-(2-Amino-7-benzyl-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid

ID: ALA124256

Chembl Id: CHEMBL124256

PubChem CID: 481401

Max Phase: Preclinical

Molecular Formula: C28H29N5O5

Molecular Weight: 515.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(N)nc2c1c(CCc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)cn2Cc1ccccc1

Standard InChI:  InChI=1S/C28H29N5O5/c1-17-24-21(16-33(25(24)32-28(29)30-17)15-19-5-3-2-4-6-19)12-9-18-7-10-20(11-8-18)26(36)31-22(27(37)38)13-14-23(34)35/h2-8,10-11,16,22H,9,12-15H2,1H3,(H,31,36)(H,34,35)(H,37,38)(H2,29,30,32)/t22-/m0/s1

Standard InChI Key:  XYVUDAYNSCLZJK-QFIPXVFZSA-N

Alternative Forms

1. Parent:

   

   ALA124256

   (2S)-2-[[4-[2-(2-amino-7-benzyl-4-methyl-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid

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: 515.57

Molecular Weight (Monoisotopic): 515.2169

AlogP: 3.20

#Rotatable Bonds: 11

Polar Surface Area: 160.43

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.34

CX Basic pKa: 7.97

CX LogP: 1.67

CX LogD: -1.96

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.24

Np Likeness Score: -0.44

References

1. Gangjee A, Yu J, McGuire JJ, Cody V, Galitsky N, Kisliuk RL, Queener SF..  (2000)  Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent.,  43  (21): [PMID:11052789] [10.1021/jm000200l]

Source

Source(1):

• Scientific Literature