1-(2,4-Diamino-pyrimidin-5-yl)-1-(3,4,5-trimethoxy-phenyl)-ethanol

ID: ALA353380

PubChem CID: 44380188

Max Phase: Preclinical

Molecular Formula: C15H20N4O4

Molecular Weight: 320.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(C)(O)c2cnc(N)nc2N)cc(OC)c1OC

Standard InChI:  InChI=1S/C15H20N4O4/c1-15(20,9-7-18-14(17)19-13(9)16)8-5-10(21-2)12(23-4)11(6-8)22-3/h5-7,20H,1-4H3,(H4,16,17,18,19)

Standard InChI Key:  IUOBEQAECXKQPZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    4.4125   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -2.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2625   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -3.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -1.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -3.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250   -1.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9875   -3.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -4.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  2  0
  4  1  1  0
  5  4  1  0
  6 10  1  0
  7  9  1  0
  8 12  1  0
  9 13  2  0
 10 11  2  0
 11  1  1  0
 12  5  2  0
 13  5  1  0
 14  3  1  0
 15  6  1  0
 16  4  1  0
 17  7  1  0
 18  8  1  0
 19  9  1  0
 20  4  1  0
 21 17  1  0
 22 18  1  0
 23 19  1  0
  6  2  2  0
  8  7  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA353380

   1-(2,4-Diaminopyrimidin-5-yl)-1-(3,4,5-trimethoxyphenyl)ethanol

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: 320.35

Molecular Weight (Monoisotopic): 320.1485

AlogP: 0.92

#Rotatable Bonds: 5

Polar Surface Area: 125.74

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: 7.03

CX LogP: 0.35

CX LogD: 0.20

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: -0.05

References

1. Hopfinger AJ..  (1981)  Inhibition of dihydrofolate reductase: structure-activity correlations of 2,4-diamino-5-benzylpyrimidines based upon molecular shape analysis.,  24  (7): [PMID:7277386] [10.1021/jm00139a010]

2. Hopfinger AJ..  (1981)  Inhibition of dihydrofolate reductase: structure-activity correlations of 2,4-diamino-5-benzylpyrimidines based upon molecular shape analysis.,  24  (7): [PMID:7277386] [10.1021/jm00139a010]

Source

Source(1):

• Scientific Literature