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

ID: ALA157434

Chembl Id: CHEMBL157434

PubChem CID: 10993870

Max Phase: Preclinical

Molecular Formula: C22H25N5O5

Molecular Weight: 439.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1[nH]c(N)nc2ncc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)c1-2

Standard InChI:  InChI=1S/C22H25N5O5/c1-2-15-18-14(11-24-19(18)27-22(23)26-15)8-5-12-3-6-13(7-4-12)20(30)25-16(21(31)32)9-10-17(28)29/h3-4,6-7,11,16H,2,5,8-10H2,1H3,(H,25,30)(H,28,29)(H,31,32)(H3,23,24,26,27)/t16-/m0/s1

Standard InChI Key:  HAHWOBDKTAQBFE-INIZCTEOSA-N

Alternative Forms

1. Parent:

   

   ALA157434

   (S)-2-{4-[2-(2-Amino-4-ethyl-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: 439.47

Molecular Weight (Monoisotopic): 439.1856

AlogP: 1.89

#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: 4.16

CX LogP: 1.91

CX LogD: -4.33

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -0.11

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