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

ID: ALA4467936

Chembl Id: CHEMBL4467936

PubChem CID: 155532591

Max Phase: Preclinical

Molecular Formula: C20H21N5O6S

Molecular Weight: 459.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(CCSc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C20H21N5O6S/c21-20-24-16-13(18(29)25-20)9-11(22-16)7-8-32-12-3-1-10(2-4-12)17(28)23-14(19(30)31)5-6-15(26)27/h1-4,9,14H,5-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t14-/m0/s1

Standard InChI Key:  HPAURQDCTYKMTE-AWEZNQCLSA-N

Alternative Forms

1. Parent:

   

   ALA4467936

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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: 459.48

Molecular Weight (Monoisotopic): 459.1213

AlogP: 1.22

#Rotatable Bonds: 10

Polar Surface Area: 191.26

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.12

CX Basic pKa: 4.72

CX LogP: -0.45

CX LogD: -5.77

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.24

Np Likeness Score: -0.35

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