5,8-deazaAminopterin

ID: ALA3244851

Cas Number: 18921-68-1

PubChem CID: 101200

Max Phase: Preclinical

Molecular Formula: C21H22N6O5

Molecular Weight: 438.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2cc(CNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C21H22N6O5/c22-18-14-9-11(1-6-15(14)26-21(23)27-18)10-24-13-4-2-12(3-5-13)19(30)25-16(20(31)32)7-8-17(28)29/h1-6,9,16,24H,7-8,10H2,(H,25,30)(H,28,29)(H,31,32)(H4,22,23,26,27)/t16-/m0/s1

Standard InChI Key:  IOLLERXPKZGYRA-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    8.9750  -11.7582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6791  -10.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3915  -11.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3915  -10.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6791  -12.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9750  -10.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1041  -12.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0915  -13.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1041  -10.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8124  -13.0290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8165  -11.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2415  -13.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2499  -11.7707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5248  -13.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3790  -13.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5291  -12.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9540  -12.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0915  -14.2582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2415  -12.2082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8165  -10.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6623  -13.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3790  -12.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9540  -13.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6665  -11.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2540  -10.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5165  -14.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2289  -14.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9540  -13.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6770  -12.9957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2279  -15.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5130  -15.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9419  -15.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  5  1  0
  4  2  1  0
  5  1  2  0
  6  1  1  0
  7  3  2  0
  8 15  1  0
  9  4  2  0
 10  8  1  0
 11  7  1  0
 12 14  1  0
 13 16  1  0
 14 10  1  6
 15 22  1  0
 16 11  1  0
 17 13  1  0
 18  8  2  0
 19 12  2  0
 20  9  1  0
 21 23  1  0
 22 24  2  0
 23 17  2  0
 24 17  1  0
 25  6  1  0
 26 14  1  0
 27 26  1  0
 28 12  1  0
  3  4  1  0
 11 20  2  0
 21 15  2  0
  5 29  1  0
 27 30  1  0
 30 31  1  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3244851

   Deazaminopterin

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: 438.44

Molecular Weight (Monoisotopic): 438.1652

AlogP: 1.45

#Rotatable Bonds: 9

Polar Surface Area: 193.55

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.53

CX Basic pKa: 7.05

CX LogP: -1.52

CX LogD: -4.67

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: -0.59

References

1. Hynes JB, Eason DE, Garrett CM, Colvin PL..  (1977)  Quinazolines as inhibitors of dihydrofolate reductase. 4. Classical analogues of folic and isofolic acids.,  20  (4): [PMID:850245] [10.1021/jm00214a030]

Source

Source(1):

• Scientific Literature