(4-{N-[2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]-pyrimidin-6-yl)ethyl]-2,2,2-trifluoroacetamido}benzoyl)-L-glutamic Acid

ID: ALA4553188

Chembl Id: CHEMBL4553188

PubChem CID: 155555353

Max Phase: Preclinical

Molecular Formula: C22H21F3N6O7

Molecular Weight: 538.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(CCN(C(=O)C(F)(F)F)c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C22H21F3N6O7/c23-22(24,25)20(38)31(8-7-11-9-13-16(27-11)29-21(26)30-18(13)35)12-3-1-10(2-4-12)17(34)28-14(19(36)37)5-6-15(32)33/h1-4,9,14H,5-8H2,(H,28,34)(H,32,33)(H,36,37)(H4,26,27,29,30,35)/t14-/m0/s1

Standard InChI Key:  FTSMBZFBGMYYIT-AWEZNQCLSA-N

Alternative Forms

1. Parent:

   

   ALA4553188

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 538.44

Molecular Weight (Monoisotopic): 538.1424

AlogP: 1.02

#Rotatable Bonds: 10

Polar Surface Area: 211.57

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.10

CX Basic pKa: 4.51

CX LogP: -0.70

CX LogD: -6.17

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.22

Np Likeness Score: -0.41

References

1. Golani LK, Wallace-Povirk A, Deis SM, Wong J, Ke J, Gu X, Raghavan S, Wilson MR, Li X, Polin L, de Waal PW, White K, Kushner J, O'Connor C, Hou Z, Xu HE, Melcher K, Dann CE, Matherly LH, Gangjee A..  (2016)  Tumor Targeting with Novel 6-Substituted Pyrrolo [2,3-d] Pyrimidine Antifolates with Heteroatom Bridge Substitutions via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis.,  59  (17): [PMID:27458733] [10.1021/acs.jmedchem.6b00594]

Source

Source(1):

• Scientific Literature