triPhosphoric acid-[3,4-dihydroxy-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester

ID: ALA1199042

Chembl Id: CHEMBL1199042

Max Phase: Preclinical

Molecular Formula: C11H18N5O13P3

Molecular Weight: 521.21

Molecule Type: Small molecule

Names and Identifiers

Synonyms: N6-Methyl-Adenosinetriphosphate

Canonical SMILES:  CNc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H18N5O13P3/c1-12-9-6-10(14-3-13-9)16(4-15-6)11-8(18)7(17)5(27-11)2-26-31(22,23)29-32(24,25)28-30(19,20)21/h3-5,7-8,11,17-18H,2H2,1H3,(H,22,23)(H,24,25)(H,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1

Standard InChI Key:  LCQWKKZWHQFOAH-IOSLPCCCSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1199042

   P-P-P-m6Ade-Ribf.4NH3

2. Parent:

   

   ALA1199042

   ---

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: 521.21

Molecular Weight (Monoisotopic): 521.0114

AlogP: -1.17

#Rotatable Bonds: 9

Polar Surface Area: 265.14

Molecular Species: ACID

HBA: 14

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.90

CX Basic pKa: 4.77

CX LogP: -5.04

CX LogD: -10.17

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.19

Np Likeness Score: 1.17

References

1. Ravi RG, Kim HS, Servos J, Zimmermann H, Lee K, Maddileti S, Boyer JL, Harden TK, Jacobson KA..  (2002)  Adenine nucleotide analogues locked in a Northern methanocarba conformation: enhanced stability and potency as P2Y(1) receptor agonists.,  45  (10): [PMID:11985476] [10.1021/jm010538v]

2. Fischer B, Boyer JL, Hoyle CH, Ziganshin AU, Brizzolara AL, Knight GE, Zimmet J, Burnstock G, Harden TK, Jacobson KA..  (1993)  Identification of potent, selective P2Y-purinoceptor agonists: structure-activity relationships for 2-thioether derivatives of adenosine 5'-triphosphate.,  36  (24): [PMID:8254622] [10.1021/jm00076a023]

3. Gillerman I, Lecka J, Simhaev L, Munkonda MN, Fausther M, Martín-Satué M, Senderowitz H, Sévigny J, Fischer B..  (2014)  2-Hexylthio-β,γ-CH2-ATP is an effective and selective NTPDase2 inhibitor.,  57  (14): [PMID:24972256] [10.1021/jm401933c]

4. Novotná B, Vaneková L, Zavřel M, Buděšínský M, Dejmek M, Smola M, Gutten O, Tehrani ZA, Pimková Polidarová M, Brázdová A, Liboska R, Štěpánek I, Vavřina Z, Jandušík T, Nencka R, Rulíšek L, Bouřa E, Brynda J, Páv O, Birkuš G..  (2019)  Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.,  62  (23): [PMID:31715099] [10.1021/acs.jmedchem.9b01062]

5. Isaak A, Dobelmann C, Füsser FT, Erlitz KS, Koch O, Junker A..  (2022)  Unveiling the Structure-Activity Relationships at the Orthosteric Binding Site of P2X Ion Channels: The Route to Selectivity.,  65  (16.0): [PMID:35930402] [10.1021/acs.jmedchem.2c00812]

Source

Source(1):

• Scientific Literature