ATP Analog

ID: ALA1230989

Cas Number: 25612-73-1

PubChem CID: 33113

Product Number: A463300, Order Now?

Max Phase: Preclinical

Molecular Formula: C10H17N6O12P3

Molecular Weight: 506.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)NP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H17N6O12P3/c11-8-5-9(13-2-12-8)16(3-14-5)10-7(18)6(17)4(27-10)1-26-31(24,25)28-30(22,23)15-29(19,20)21/h2-4,6-7,10,17-18H,1H2,(H,24,25)(H2,11,12,13)(H4,15,19,20,21,22,23)/t4-,6-,7-,10-/m1/s1

Standard InChI Key:  PVKSNHVPLWYQGJ-KQYNXXCUSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.4628   -4.0011    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1302   -4.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9779   -4.6685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9477   -3.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816   -2.6957    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611   -2.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7021   -2.7819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7953   -3.5162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004   -1.3903    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8154   -2.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -0.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9678   -1.8752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329   -0.9054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    1.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    0.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9878   -0.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2178    0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0428    0.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    1.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9878    2.2646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    2.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9878    3.5995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725    3.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869    4.5820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2014    3.3445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2014    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869    2.1070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  8  1  1  0
  6  5  2  0
  5  7  1  0
  5  8  1  0
 12  5  1  0
 10  9  2  0
  9 11  1  0
  9 12  1  0
 13  9  1  0
 14 13  1  0
 15 14  1  1
 15 16  1  0
 17 15  1  0
 21 16  1  0
 17 18  1  6
 19 17  1  0
 19 20  1  6
 21 19  1  0
 21 22  1  1
 23 22  1  0
 31 22  1  0
 23 24  2  0
 25 24  1  0
 25 26  1  0
 31 25  2  0
 26 27  1  0
 26 28  2  0
 29 28  1  0
 29 30  2  0
 31 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1230989

   Adenosine 5′-(β,γ-imido)triphosphate lithium salt hydrate

2. Alternative Forms:

   

   ALA1230989

   AMP PNP

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: 506.20

Molecular Weight (Monoisotopic): 506.0117

AlogP: -2.06

#Rotatable Bonds: 8

Polar Surface Area: 281.93

Molecular Species: ACID

HBA: 13

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.34

CX Basic pKa: 4.92

CX LogP: -5.96

CX LogD: -12.58

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.18

Np Likeness Score: 1.24

References

1. Bystrom CE, Pettigrew DW, Remington S, Branchaud BP.  (1997)  ATP analogs with non-transferable groups in the position as inhibitors of glycerol kinase,  7  (20): [10.1016/S0960-894X(97)10051-8]

2. Kappler F, Hai TT, Hampton A..  (1986)  Isozyme-specific enzyme inhibitors. 10. Adenosine 5'-triphosphate derivatives as substrates or inhibitors of methionine adenosyltransferases of rat normal and hepatoma tissues.,  29  (3): [PMID:3950912] [10.1021/jm00153a003]

3. Shakya T, Wright GD..  (2010)  Nucleotide selectivity of antibiotic kinases.,  54  (5): [PMID:20231391] [10.1128/aac.01570-09]

4. Elliott TS, Slowey A, Ye Y, Conway SJ.  (2012)  The use of phosphate bioisosteres in medicinal chemistry and chemical biology,  3  (7): [10.1039/C2MD20079A]

5. Arora R, Di Michele M, Stes E, Vandermarliere E, Martens L, Gevaert K, Van Heerde E, Linders JT, Brehmer D, Jacoby E, Bonnet P..  (2015)  Structural investigation of B-Raf paradox breaker and inducer inhibitors.,  58  (4): [PMID:25611072] [10.1021/jm501667n]

6. Labrière C, Talapatra SK, Thoret S, Bougeret C, Kozielski F, Guillou C..  (2016)  New MKLP-2 inhibitors in the paprotrain series: Design, synthesis and biological evaluations.,  24  (4): [PMID:26778612] [10.1016/j.bmc.2015.12.042]

7. Kumar Mv V, Ebna Noor R, Davis RE, Zhang Z, Sipavicius E, Keramisanou D, Blagg BSJ, Gelis I..  (2018)  Molecular insights into the interaction of Hsp90 with allosteric inhibitors targeting the C-terminal domain.,  9  (8): [PMID:30151087] [10.1039/C8MD00151K]

8. Wilke KE, Fihn CA, Carlson EE..  (2018)  Screening serine/threonine and tyrosine kinase inhibitors for histidine kinase inhibition.,  26  (19): [PMID:29706527] [10.1016/j.bmc.2018.04.047]

9. Bestgen B, Krimm I, Kufareva I, Kamal AAM, Seetoh WG, Abell C, Hartmann RW, Abagyan R, Cochet C, Le Borgne M, Engel M, Lomberget T..  (2019)  2-Aminothiazole Derivatives as Selective Allosteric Modulators of the Protein Kinase CK2. 1. Identification of an Allosteric Binding Site.,  62  (4): [PMID:30689953] [10.1021/acs.jmedchem.8b01766]

10. Blay V, Gailiunaite S, Lee CY, Chang HY, Hupp T, Houston DR, Chi P..  (2022)  Comparison of ATP-binding pockets and discovery of homologous recombination inhibitors.,  70  [PMID:35841829] [10.1016/j.bmc.2022.116923]

Source

Source(1):

• Scientific Literature