2-{4-[2-(2,4-Diamino-pteridin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid

ID: ALA293263

Cas Number: 52454-37-2

PubChem CID: 100516

Max Phase: Preclinical

Molecular Formula: C20H21N7O5

Molecular Weight: 439.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GNF-Pf-173 | 10-Deazaaminopterin|52454-37-2|10-Deazaminopterin|10-Deaza-aminopterin|GNF-PF-173|PXJ16PPE04|CHEMBL293263|L-Glutamic acid, N-(4-(2-(2,4-diamino-6-pteridinyl)ethyl)benzoyl)-|(2S)-2-[[4-[2-(2,4-diaminopteridin-6-yl)ethyl]benzoyl]amino]pentanedioic acid|(4-(2-(2,4-diaminopteridin-6-yl)ethyl)benzoyl)-L-glutamic acid|UNII-PXJ16PPE04|NSC 311469|NSC-311469|10-DAM|SCHEMBL7081697|BDBM50016461|AKOS040746467|HY-125647|CS-0092602|Q27286805|(S)-2-(4-(2-(2,4-Diaminopteridin-6-yl)ethyl)benzamido)pShow More⌵

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

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.6486    1.3517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -2.6973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4942   -1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7933   -0.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0923   -1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0923   -2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7933   -3.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4943   -2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3906   -3.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4308   -3.1467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3885   -5.2457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6867   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6846   -7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9828   -8.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9807   -9.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9405  -10.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0187  -10.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9893   -5.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9934   -4.0533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0266   -5.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  2  0
 17 19  1  0
 20 19  1  6
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 20 26  1  0
 26 27  1  0
 26 28  2  0
  8 29  1  0
 29 30  2  0
 30 31  1  0
 31  6  1  0
 31 32  2  0
 32  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA293263

   10-Deazaaminopterin

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: 439.43

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: ┄

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