ID: ALA220940

Max Phase: Preclinical

Molecular Formula: C10H17N2O15P3

Molecular Weight: 498.17

Molecule Type: Small molecule

Representations

Synonyms (2): Thymidine Triphosphate | Thymidine-5'-triphosphate
Synonyms from Alternative Forms(2):

Canonical SMILES:  Cc1cn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C10H17N2O15P3/c1-4-2-12(10(16)11-8(4)15)9-7(14)6(13)5(25-9)3-24-29(20,21)27-30(22,23)26-28(17,18)19/h2,5-7,9,13-14H,3H2,1H3,(H,20,21)(H,22,23)(H,11,15,16)(H2,17,18,19)/t5-,6-,7-,9-/m1/s1

Standard InChI Key:  RZCIEJXAILMSQK-JXOAFFINSA-N

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

Properties

Molecular Weight: 498.17

Molecular Weight (Monoisotopic): 497.9842

AlogP: -2.19

#Rotatable Bonds: 8

Polar Surface Area: 264.37

Molecular Species: ACID

HBA: 12

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.90

CX Basic pKa:

CX LogP: -2.99

CX LogD: -10.40

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.19

Np Likeness Score: 1.30

References

1. von Janta-Lipinski M, Costisella B, Ochs H, Hübscher U, Hafkemeyer P, Matthes E..  (1998)  Newly synthesized L-enantiomers of 3'-fluoro-modified beta-2'-deoxyribonucleoside 5'-triphosphates inhibit hepatitis B DNA polymerases but not the five cellular DNA polymerases alpha, beta, gamma, delta, and epsilon nor HIV-1 reverse transcriptase.,  41  (12): [PMID:9622545] [10.1021/jm9704210]

2. Chawla RR, Freed JJ, Kappler F, Hampton A..  (1986)  Zwitterionic 3'-O-acyl derivatives of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in cells in culture.,  29  (5): [PMID:3701790] [10.1021/jm00155a033]

3. Hampton A, Hai TT, Kappler F, Chawla RR..  (1982)  Species- or isozyme-specific enzyme inhibitors. 6. Synthesis and evaluation of two-substrate condensation products as inhibitors of hexokinases and thymidine kinases.,  25  (7): [PMID:7108896] [10.1021/jm00349a007]

4. Okamoto A, Tanaka K, Saito I..  (2002)  2-Amino-7-deazaadenine forms stable base pairs with cytosine and thymine.,  12  (1): [PMID:11738582] [10.1016/s0960-894x(01)00685-0]

5. Ivanov AA, Ko H, Cosyn L, Maddileti S, Besada P, Fricks I, Costanzi S, Harden TK, Calenbergh SV, Jacobson KA..  (2007)  Molecular modeling of the human P2Y2 receptor and design of a selective agonist, 2'-amino-2'-deoxy-2-thiouridine 5'-triphosphate.,  50  (6): [PMID:17302398] [10.1021/jm060903o]

6. Zhang HW, Detorio M, Herman BD, Solomon S, Bassit L, Nettles JH, Obikhod A, Tao SJ, Mellors JW, Sluis-Cremer N, Coats SJ, Schinazi RF..  (2011)  Synthesis, antiviral activity, cytotoxicity and cellular pharmacology of l-3'-azido-2',3'-dideoxypurine nucleosides.,  46  (9): [PMID:21700368] [10.1016/j.ejmech.2011.05.051]

Source

Source(1):

• Scientific Literature