((4-(2-(cis-4-aminocyclohexyl)-9-ethyl-9H-purin-6-ylamino)phenyl)(hydroxy)phosphoryl)methylphosphonic acid

ID: ALA1084268

PubChem CID: 11957378

Max Phase: Preclinical

Molecular Formula: C20H28N6O5P2

Molecular Weight: 494.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: AP-23451 | CHEMBL1084268|{[(4-{[2-(4-AMINOCYCLOHEXYL)-9-ETHYL-9H-PURIN-6-YL]AMINO}PHENYL)(HYDROXY)PHOSPHORYL]METHYL}PHOSPHONIC ACID|2bdf|24A|ap23451|2,6,9-Trisubstituted Purine, 8|BDBM50318870|AP-23451|2,6,9-Trisubstituted Purine, AP23451|Q27452692|((4-(2-(cis-4-aminocyclohexyl)-9-ethyl-9H-purin-6-ylamino)phenyl)(hydroxy)phosphoryl)methylphosphonic acid|[[4-[[2-(4-aminocyclohexyl)-9-ethylpurin-6-yl]amino]phenyl]-hydroxyphosphoryl]methylphosphonic acid|{[(R)-(4-{[2-(trans-4-aminocyclohexyl)-9-ethShow More⌵

Canonical SMILES:  CCn1cnc2c(Nc3ccc(P(=O)(O)CP(=O)(O)O)cc3)nc([C@H]3CC[C@H](N)CC3)nc21

Standard InChI:  InChI=1S/C20H28N6O5P2/c1-2-26-11-22-17-19(24-18(25-20(17)26)13-3-5-14(21)6-4-13)23-15-7-9-16(10-8-15)32(27,28)12-33(29,30)31/h7-11,13-14H,2-6,12,21H2,1H3,(H,27,28)(H,23,24,25)(H2,29,30,31)/t13-,14-

Standard InChI Key:  FGMSUCIOAMNCKF-HDJSIYSDSA-N

Molfile:  

     RDKit          2D

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   10.9771   -5.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6915   -5.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4106   -5.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.8356   -3.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1241   -3.4737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   14.5419   -0.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6854   -0.5788    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.4013   -0.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1143   -0.5733    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   18.1111    0.2517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6822    0.2462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1086   -1.3979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6240   -1.3704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7483   -5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5733   -5.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2625   -5.9491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9 16  1  0
  8 12  1  0
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  1  6  1  0
 17 18  2  0
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 18 19  1  0
  2  3  1  0
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  9 10  2  0
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 10  7  1  0
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  5  7  1  1
 20 23  1  0
 11 12  2  0
 23 24  1  0
  3  4  1  0
 24 25  1  0
  5  4  1  0
 25 26  1  0
  5  6  1  0
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  1  2  1  0
 25 29  1  0
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 31 32  1  0
 15 11  1  0
  7  8  2  0
  2 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1084268

   {[(4-{[2-(4-Aminocyclohexyl)-9-ethyl-9H-purin-6-YL]amino}phenyl)(hydroxy)phosphoryl]methyl}phosphonic acid

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: 494.43

Molecular Weight (Monoisotopic): 494.1596

AlogP: 2.61

#Rotatable Bonds: 7

Polar Surface Area: 176.48

Molecular Species: ZWITTERION

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.53

CX Basic pKa: 10.45

CX LogP: -1.31

CX LogD: -2.47

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -0.72

References

1. Allen JG, Fotsch C, Babij P..  (2010)  Emerging targets in osteoporosis disease modification.,  53  (11): [PMID:20218623] [10.1021/jm9018756]

Source

Source(1):

• Scientific Literature