(S)-2-{4-[2-(2-Amino-4-ethyl-6-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid

ID: ALA154935

Chembl Id: CHEMBL154935

PubChem CID: 11826533

Max Phase: Preclinical

Molecular Formula: C23H27N5O5

Molecular Weight: 453.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1[nH]c(N)nc2nc(C)c(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)c1-2

Standard InChI:  InChI=1S/C23H27N5O5/c1-3-16-19-15(12(2)25-20(19)28-23(24)27-16)9-6-13-4-7-14(8-5-13)21(31)26-17(22(32)33)10-11-18(29)30/h4-5,7-8,17H,3,6,9-11H2,1-2H3,(H,26,31)(H,29,30)(H,32,33)(H3,24,25,27,28)/t17-/m0/s1

Standard InChI Key:  IKBNTIZRQVNJHZ-KRWDZBQOSA-N

Alternative Forms

1. Parent:

   

   ALA154935

   (S)-2-{4-[2-(2-Amino-4-ethyl-6-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-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: 453.50

Molecular Weight (Monoisotopic): 453.2012

AlogP: 2.20

#Rotatable Bonds: 10

Polar Surface Area: 171.29

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.34

CX Basic pKa: 2.85

CX LogP: 1.86

CX LogD: -4.20

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -0.21

References

1. 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