7,8-dihydrohomofolic acid

ID: ALA3275224

PubChem CID: 135720406

Max Phase: Preclinical

Molecular Formula: C20H23N7O6

Molecular Weight: 457.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)c2c([nH]1)NCC(CCNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)=N2

Standard InChI:  InChI=1S/C20H23N7O6/c21-20-26-16-15(18(31)27-20)24-12(9-23-16)7-8-22-11-3-1-10(2-4-11)17(30)25-13(19(32)33)5-6-14(28)29/h1-4,13,22H,5-9H2,(H,25,30)(H,28,29)(H,32,33)(H4,21,23,26,27,31)/t13-/m0/s1

Standard InChI Key:  VEBDSVCWCXWVOS-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   21.7105  -11.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2965  -11.5018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0028  -11.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9974  -12.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7037  -13.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6983  -13.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9906  -14.3666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4046  -14.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7118  -10.6899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4168  -11.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5847  -11.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8783  -11.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1706  -11.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4643  -11.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4656  -10.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1774  -10.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8838  -10.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5833  -12.7270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7634  -10.2607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0516  -10.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3452  -10.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5062  -11.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7999  -11.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8053  -10.6486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5171  -10.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2235  -10.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9312  -10.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6375  -10.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6321  -11.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9244  -11.8844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2180  -11.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5185   -9.4234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0922  -11.8697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  6
  1  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  2  0
  1 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 11 18  2  0
 20 21  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 22 31  1  0
 26 31  2  0
 25 32  2  0
 23 33  1  0
 21 28  1  0
 19 20  1  0
 15 19  1  0
  2 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3275224

   ---

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: 457.45

Molecular Weight (Monoisotopic): 457.1710

AlogP: 0.40

#Rotatable Bonds: 10

Polar Surface Area: 211.89

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.60

CX Basic pKa: 4.52

CX LogP: -2.44

CX LogD: -7.77

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.26

Np Likeness Score: -0.13

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