ID: ALA4437824

Max Phase: Preclinical

Molecular Formula: C20H22N6O6

Molecular Weight: 442.43

Molecule Type: Unknown

Representations

Canonical SMILES:  Nc1nc2[nH]c(CCNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C20H22N6O6/c21-20-25-16-13(18(30)26-20)9-12(23-16)7-8-22-11-3-1-10(2-4-11)17(29)24-14(19(31)32)5-6-15(27)28/h1-4,9,14,22H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,21,23,25,26,30)/t14-/m0/s1

Standard InChI Key:  UFNWIIALSMNORN-AWEZNQCLSA-N

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

Properties

Molecular Weight: 442.43

Molecular Weight (Monoisotopic): 442.1601

AlogP: 0.54

#Rotatable Bonds: 10

Polar Surface Area: 203.29

Molecular Species: ACID

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.30

CX Basic pKa: 4.81

CX LogP: -1.78

CX LogD: -6.67

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.23

Np Likeness Score: -0.24

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]

2. Golani LK, Islam F, O'Connor C, Dekhne AS, Hou Z, Matherly LH, Gangjee A..  (2020)  Design, synthesis and biological evaluation of novel pyrrolo[2,3-d]pyrimidine as tumor-targeting agents with selectivity for tumor uptake by high affinity folate receptors over the reduced folate carrier.,  28  (12): [PMID:32503687] [10.1016/j.bmc.2020.115544]

Source

Source(1):

• Scientific Literature