7,8-Dihydro-10-oxafolic acid

ID: ALA3275223

PubChem CID: 136504164

Max Phase: Preclinical

Molecular Formula: C19H20N6O7

Molecular Weight: 444.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)c2c([nH]1)NCC(COc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)=N2

Standard InChI:  InChI=1S/C19H20N6O7/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:  PNAHURXYZLFRPS-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    4.1568   -5.0374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556   -5.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8705   -6.2776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8687   -4.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5840   -5.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5847   -5.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3001   -6.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0150   -5.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0103   -5.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2944   -4.6195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4409   -6.2767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7222   -4.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4392   -5.0181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1511   -4.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8658   -5.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5773   -4.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5726   -3.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8507   -3.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1422   -3.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2840   -3.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0015   -3.7602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2779   -2.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7129   -3.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4304   -3.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7068   -2.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4182   -2.0997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9893   -2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4365   -4.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1540   -4.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1601   -5.8067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8654   -4.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8661   -3.7996    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:

   

   ALA3275223

   ---

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: 444.40

Molecular Weight (Monoisotopic): 444.1393

AlogP: -0.02

#Rotatable Bonds: 9

Polar Surface Area: 209.09

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.93

CX Basic pKa: 3.53

CX LogP: -2.02

CX LogD: -7.82

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: -0.01

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