7,8-dihydro-10-thiofolic acid

ID: ALA3275225

PubChem CID: 136504165

Max Phase: Preclinical

Molecular Formula: C19H20N6O6S

Molecular Weight: 460.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)c2c([nH]1)NCC(CSc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)=N2

Standard InChI:  InChI=1S/C19H20N6O6S/c20-19-24-15-14(17(29)25-19)22-10(7-21-15)8-32-11-3-1-9(2-4-11)16(28)23-12(18(30)31)5-6-13(26)27/h1-4,12H,5-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,20,21,24,25,29)/t12-/m0/s1

Standard InChI Key:  KPENJEPBRSFIHQ-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.5027   -5.6498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014   -6.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2163   -6.8901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2145   -5.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9298   -5.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9305   -6.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6459   -6.8840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3608   -6.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3561   -5.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6402   -5.2321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7867   -6.8891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0680   -5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7850   -5.6306    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4969   -5.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2116   -5.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9231   -5.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9184   -4.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1965   -3.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4880   -4.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6299   -3.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3473   -4.3727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6237   -3.1406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0587   -3.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7762   -4.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0526   -3.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7640   -2.7122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3351   -2.7228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7823   -5.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4999   -5.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5059   -6.4192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2112   -5.1765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2120   -4.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
 20 22  2  0
 23 21  1  6
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
 24 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
  4 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3275225

   ---

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: 460.47

Molecular Weight (Monoisotopic): 460.1165

AlogP: 0.69

#Rotatable Bonds: 9

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: 2.99

CX Basic pKa: 3.55

CX LogP: -1.49

CX LogD: -7.30

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.19

References

1. Nair MG, Campbell PT..  (1976)  Folate analogues altered in the C9-N10 bridge region. 10-Oxafolic acid and 10-oxaaminopterin.,  19  (6): [PMID:820858] [10.1021/jm00228a018]

Source

Source(1):

• Scientific Literature