6'(R)-9-(5',6',7'-Deoxy-6'-amine-7'-cyclohexyl-beta-D-heptafuranoside-1')adenine

ID: ALA4077793

PubChem CID: 137650973

Max Phase: Preclinical

Molecular Formula: C18H28N6O3

Molecular Weight: 376.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](C[C@H](N)CC2CCCCC2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C18H28N6O3/c19-11(6-10-4-2-1-3-5-10)7-12-14(25)15(26)18(27-12)24-9-23-13-16(20)21-8-22-17(13)24/h8-12,14-15,18,25-26H,1-7,19H2,(H2,20,21,22)/t11-,12-,14-,15-,18-/m1/s1

Standard InChI Key:  MKVRCQVBVNSXAB-AJKMGBEJSA-N

Molfile:  

     RDKit          2D

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    8.0288   -3.5823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435   -5.3394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7683   -5.3894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5915   -3.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2706   -3.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0397   -4.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272   -4.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9518   -3.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1603   -3.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704   -4.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779   -4.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725   -5.0780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0393   -2.7151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2212   -2.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3536   -3.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7281   -4.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8753   -4.8084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6474   -5.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2727   -4.5486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1223   -3.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7432   -3.2145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1908   -4.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010   -4.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152   -4.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -5.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961   -5.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3876   -5.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  4  1  0
  8  7  1  0
  4  5  1  0
  7  6  1  0
  5  6  1  0
  8  9  1  1
  5  1  1  1
  6  2  1  6
  7  3  1  6
  9 10  1  0
 10 11  1  0
 10 12  1  6
  1 16  1  0
 15 13  1  0
 13 14  2  0
 14  1  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 20 21  1  0
 11 22  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4077793

   ---

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: 376.46

Molecular Weight (Monoisotopic): 376.2223

AlogP: 0.72

#Rotatable Bonds: 5

Polar Surface Area: 145.33

Molecular Species: BASE

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.48

CX Basic pKa: 10.07

CX LogP: 0.40

CX LogD: -2.11

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: 0.94

References

1. Liu Q, Cai X, Yang D, Chen Y, Wang Y, Shao L, Wang MW..  (2017)  Cycloalkane analogues of sinefungin as EHMT1/2 inhibitors.,  25  (17): [PMID:28739157] [10.1016/j.bmc.2017.06.032]

Source

Source(1):

• Scientific Literature