N10-tosylisohomopteroic acid

ID: ALA3249768

PubChem CID: 136498761

Max Phase: Preclinical

Molecular Formula: C22H20N6O5S

Molecular Weight: 480.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H20N6O5S/c1-13-2-8-17(9-3-13)34(32,33)28(11-14-4-6-15(7-5-14)21(30)31)12-16-10-24-19-18(25-16)20(29)27-22(23)26-19/h2-10H,11-12H2,1H3,(H,30,31)(H3,23,24,26,27,29)

Standard InChI Key:  VMKSRWCJAYYFJO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   15.4751  -15.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8918  -15.2835    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0664  -15.2789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6070  -14.4793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6059  -15.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3206  -15.7195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3189  -14.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0343  -14.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0350  -15.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7504  -15.7135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4653  -15.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4606  -14.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7447  -14.0614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8911  -15.7186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3164  -13.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1725  -14.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8895  -14.4600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6015  -14.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5900  -13.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3013  -12.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2910  -11.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5708  -11.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8594  -11.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8731  -12.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6115  -15.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6149  -16.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3310  -16.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0440  -16.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0363  -15.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3196  -15.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7615  -16.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5590  -10.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2676  -10.3214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8388  -10.3417    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:

   

   ALA3249768

   ---

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: 480.51

Molecular Weight (Monoisotopic): 480.1216

AlogP: 2.11

#Rotatable Bonds: 7

Polar Surface Area: 172.49

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.09

CX Basic pKa: 2.79

CX LogP: 2.35

CX LogD: -0.52

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: -1.11

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