ID: ALA293263

Max Phase: Preclinical

Molecular Formula: C20H21N7O5

Molecular Weight: 439.43

Molecule Type: Small molecule

Representations

Synonyms (1): GNF-Pf-173
Synonyms from Alternative Forms(1):

Canonical SMILES:  Nc1nc(N)c2nc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1

Standard InChI:  InChI=1S/C20H21N7O5/c21-16-15-17(27-20(22)26-16)23-9-12(24-15)6-3-10-1-4-11(5-2-10)18(30)25-13(19(31)32)7-8-14(28)29/h1-2,4-5,9,13H,3,6-8H2,(H,25,30)(H,28,29)(H,31,32)(H4,21,22,23,26,27)/t13-/m0/s1

Standard InChI Key:  LGFLRHWJJKLPCC-ZDUSSCGKSA-N

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

Properties

Molecular Weight: 439.43

Molecular Weight (Monoisotopic): 439.1604

AlogP: 0.42

#Rotatable Bonds: 9

Polar Surface Area: 207.30

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.34

CX Basic pKa: 2.88

CX LogP: 0.27

CX LogD: -6.04

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -0.17

References

1. Nair MG, Bridges TW, Henkel TJ, Kisliuk RL, Gaumont Y, Sirotnak FM..  (1981)  Folate analogues altered in the C9-N10 bridge region. 18. Synthesis and antitumor evaluation of 11-oxahomoaminopterin and related compounds.,  24  (9): [PMID:6793726] [10.1021/jm00141a010]

2. DeGraw JI, Brown VH, Tagawa H, Kisliuk RL, Gaumont Y, Sirotnak FM..  (1982)  Synthesis and antitumor activity of 10-alkyl-10-deazaminopterins. A convenient synthesis of 10-deazaminopterin.,  25  (10): [PMID:7143361] [10.1021/jm00352a026]

3. Nair MG, Nanavati NT, Kumar P, Gaumont Y, Kisliuk RL..  (1988)  Synthesis and biological evaluation of poly-gamma-glutamyl metabolites of 10-deazaaminopterin and 10-ethyl-10-deazaaminopterin.,  31  (1): [PMID:2447278] [10.1021/jm00396a029]

4. DeGraw JI, Christie PH, Kisliuk RL, Gaumont Y, Sirotnak FM..  (1990)  Synthesis and antifolate properties of 9-alkyl-10-deazaminopterins.,  33  (1): [PMID:2296020] [10.1021/jm00163a035]

5. DeGraw JI, Colwell WT, Piper JR, Sirotnak FM..  (1993)  Synthesis and antitumor activity of 10-propargyl-10-deazaaminopterin.,  36  (15): [PMID:8340923] [10.1021/jm00067a020]

6. Abraham A, McGuire JJ, Galivan J, Nimec Z, Kisliuk RL, Gaumont Y, Nair MG..  (1991)  Folate analogues. 34. Synthesis and antitumor activity of non-polyglutamylatable inhibitors of dihydrofolate reductase.,  34  (1): [PMID:1992121] [10.1021/jm00105a035]

7. DeGraw JI, Colwell WT, Crase J, Smith RL, Piper JR, Waud WR, Sirotnak FM..  (1997)  Analogues of methotrexate in rheumatoid arthritis. 1. Effects of 10-deazaaminopterin analogues on type II collagen-induced arthritis in mice.,  40  (3): [PMID:9022804] [10.1021/jm9505526]

Source

Source(1):

• Scientific Literature