((2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyltriphosphoric acid

ID: ALA1201369

Chembl Id: CHEMBL1201369

PubChem CID: 135544356

Max Phase: Unknown

Molecular Formula: C10H16N5O14P3

Molecular Weight: 523.18

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 9beta-d-arabinofuranosylguanosine 5'-triphosphate | Gtp

Canonical SMILES:  Nc1nc(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@@H]3O)c2[nH]1

Standard InChI:  InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6+,9-/m1/s1

Standard InChI Key:  XKMLYUALXHKNFT-FJFJXFQQSA-N

Alternative Forms

1. Parent:

   

   ALA1201369

   GTP

Molecule Features

Natural Product: Yes

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: 523.18

Molecular Weight (Monoisotopic): 522.9907

AlogP: -2.34

#Rotatable Bonds: 8

Polar Surface Area: 299.10

Molecular Species: ACID

HBA: 14

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.71

CX Basic pKa: 2.39

CX LogP: -3.36

CX LogD: -10.56

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.17

Np Likeness Score: 1.23

References

1. Toth M, Frase H, Chow JW, Smith C, Vakulenko SB..  (2010)  Mutant APH(2'')-IIa enzymes with increased activity against amikacin and isepamicin.,  54  (4): [PMID:20145089] [10.1128/aac.01444-09]

2. PubChem BioAssay data set, 

3. Steeves CH, Bearne SL..  (2011)  Activation and inhibition of CTP synthase from Trypanosoma brucei, the causative agent of African sleeping sickness.,  21  (18): [PMID:21840216] [10.1016/j.bmcl.2011.07.054]

4. Kaul M, Parhi AK, Zhang Y, LaVoie EJ, Tuske S, Arnold E, Kerrigan JE, Pilch DS..  (2012)  A bactericidal guanidinomethyl biaryl that alters the dynamics of bacterial FtsZ polymerization.,  55  (22): [PMID:23050700] [10.1021/jm3012728]

5. Hampton A, Kappler F, Chawla RR..  (1979)  Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.,  22  (6): [PMID:458818] [10.1021/jm00192a005]

6. Köse M, Ritter K, Thiemke K, Gillard M, Kostenis E, Müller CE..  (2014)  Development of [(3)H]2-Carboxy-4,6-dichloro-1H-indole-3-propionic Acid ([(3)H]PSB-12150): A Useful Tool for Studying GPR17.,  5  (4): [PMID:24900835] [10.1021/ml400399f]

7. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Active Ingredient of a Prodrug