7,8-dihydro-11-thiohomofolic acid

ID: ALA3245580

PubChem CID: 136502413

Max Phase: Preclinical

Molecular Formula: C20H22N6O6S

Molecular Weight: 474.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)c2c([nH]1)NCC(CCSc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)=N2

Standard InChI:  InChI=1S/C20H22N6O6S/c21-20-25-16-15(18(30)26-20)23-11(9-22-16)7-8-33-12-3-1-10(2-4-12)17(29)24-13(19(31)32)5-6-14(27)28/h1-4,13H,5-9H2,(H,24,29)(H,27,28)(H,31,32)(H4,21,22,25,26,30)/t13-/m0/s1

Standard InChI Key:  ULIQZSQMVSOUFB-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    8.8491  -10.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1348  -11.0247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4211   -9.7845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7036   -9.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2857  -11.8048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4200  -10.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0215  -14.6868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4320  -12.2013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9866   -9.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2979  -13.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1331  -10.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8491  -10.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7146  -11.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5926  -14.6974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5544   -9.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1305   -8.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3041  -14.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1324   -9.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4155   -9.3484    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5588   -9.3668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2795  -10.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1329   -9.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7084  -10.9692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2747   -9.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0093  -13.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5620  -10.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9909  -10.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8377   -9.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0032  -12.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8484   -9.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5645  -11.0187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7052  -11.0238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2794  -10.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 30 22  1  0
 21 27  2  0
 31 33  1  0
 26 15  1  0
 22  3  1  0
 28 18  1  0
  6 32  1  0
 15 28  2  0
 20 30  1  0
 18 11  2  0
 26 21  1  0
 12 26  2  0
 25 10  1  0
 13  8  1  0
  4 19  1  0
 10 17  1  0
  2  1  1  0
 19 18  1  0
 17 14  2  0
  9  4  1  0
 29 13  1  0
 17  7  1  0
  1 31  1  0
 21  5  1  0
 13 23  2  0
 22 16  2  0
 29  5  1  6
 30  1  2  0
 24  9  1  0
  3  6  2  0
 24 20  2  0
 11 12  1  0
 29 25  1  0
 33 24  1  0
  6  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3245580

   ---

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: 474.50

Molecular Weight (Monoisotopic): 474.1322

AlogP: 1.08

#Rotatable Bonds: 10

Polar Surface Area: 199.86

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.13

CX Basic pKa: 3.58

CX LogP: -1.08

CX LogD: -6.85

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: -0.24

References

1. Nair MG, Chen SY, Kisliuk RL, Gaumont Y, Strumpf D..  (1979)  Folate analogues altered in the C9-N10 bridge region: 11-thiohomofolic acid.,  22  (7): [PMID:109615] [10.1021/jm00193a019]

Source

Source(1):

• Scientific Literature