4-amino-4-deoxy-N10-tosylisohomopteroic acid

ID: ALA3249765

PubChem CID: 90673953

Max Phase: Preclinical

Molecular Formula: C22H21N7O4S

Molecular Weight: 479.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)N(Cc2ccc(C(=O)O)cc2)Cc2cnc3nc(N)nc(N)c3n2)cc1

Standard InChI:  InChI=1S/C22H21N7O4S/c1-13-2-8-17(9-3-13)34(32,33)29(11-14-4-6-15(7-5-14)21(30)31)12-16-10-25-20-18(26-16)19(23)27-22(24)28-20/h2-10H,11-12H2,1H3,(H,30,31)(H4,23,24,25,27,28)

Standard InChI Key:  PILROWOHAPGMNP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   17.4664   -7.3671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8792   -6.6613    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.0616   -6.6568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6349   -5.8648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6338   -6.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3418   -7.0933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3401   -5.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0487   -5.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0494   -6.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7580   -7.0872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4662   -6.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4615   -5.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7524   -5.4509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9258   -7.0923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3376   -4.6387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1667   -5.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8769   -5.8457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5821   -5.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5707   -4.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2753   -4.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2651   -3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5517   -2.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8470   -3.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8606   -4.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5920   -7.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5954   -7.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3047   -8.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0109   -7.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0033   -7.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2934   -6.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7216   -8.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5401   -2.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2419   -1.7463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8266   -1.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  5 14  1  0
  7 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 17  2  1  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 22 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3249765

   4-[[(2,4-Diaminopteridin-6-yl)methyl-(4-methylphenyl)sulfonylamino]methyl]benzoic acid

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: 479.52

Molecular Weight (Monoisotopic): 479.1376

AlogP: 1.98

#Rotatable Bonds: 7

Polar Surface Area: 178.28

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.07

CX Basic pKa: 1.80

CX LogP: 2.07

CX LogD: -1.05

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.35

Np Likeness Score: -1.08

References

1. Nair MG, O'Neal PC, Baugh CM, Kisliuk RL, Gaumont Y, Rodman M..  (1978)  Folate analogues altered in the C9-N10 bridge region: N10-Toxylisohomofolic acid and N10-Toxylisohomoaminopterin.,  21  (7): [PMID:97383] [10.1021/jm00205a015]

Source

Source(1):

• Scientific Literature