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

ID: ALA439973

Chembl Id: CHEMBL439973

PubChem CID: 5288461

Max Phase: Preclinical

Molecular Formula: C21H23N5O5

Molecular Weight: 425.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(N)nc2[nH]cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)c12

Standard InChI:  InChI=1S/C21H23N5O5/c1-11-17-14(10-23-18(17)26-21(22)24-11)7-4-12-2-5-13(6-3-12)19(29)25-15(20(30)31)8-9-16(27)28/h2-3,5-6,10,15H,4,7-9H2,1H3,(H,25,29)(H,27,28)(H,30,31)(H3,22,23,24,26)/t15-/m0/s1

Standard InChI Key:  FICRNCFTTZHHPO-HNNXBMFYSA-N

Alternative Forms

1. Parent:

   

   ALA439973

   n-[4-[2-(2-Amino-4-methyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoyl]glutamic 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: 425.45

Molecular Weight (Monoisotopic): 425.1699

AlogP: 1.68

#Rotatable Bonds: 9

Polar Surface Area: 171.29

Molecular Species: ZWITTERION

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.34

CX Basic pKa: 8.53

CX LogP: -0.33

CX LogD: -3.49

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.34

Np Likeness Score: -0.08

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]

2. Gangjee A, Yu J, Kisliuk RL, Haile WH, Sobrero G, McGuire JJ..  (2003)  Design, synthesis, and biological activities of classical N-[4-[2-(2-amino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-l-glutamic acid and its 6-methyl derivative as potential dual inhibitors of thymidylate synthase and dihydrofolate reductase and as potential antitumor agents.,  46  (4): [PMID:12570380] [10.1021/jm0203534]

Source

Source(1):

• Scientific Literature