(beta-L-) TTPTriphosphoric acid-[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester 4M triethyl amine

ID: ALA220940

Chembl Id: CHEMBL220940

Cas Number: 23198-01-8

PubChem CID: 451388

Max Phase: Preclinical

Molecular Formula: C10H17N2O15P3

Molecular Weight: 498.17

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Thymidine Triphosphate | Thymidine-5'-triphosphate | 5-methyl-UTP|5-Methyluridine triphosphate|5-methyluridine 5'-triphosphate|Ribothymidine 5'-triphosphate|26L4U23SYM|ribothymidine triphosphate|5-methyluridine 5'-(tetrahydrogen triphosphate)|Uridine, 5-methyl-, 5'-triphosphate|UNII-26L4U23SYM|CHEMBL220940|23198-01-8|CHEBI:63550|Uridine 5'-(tetrahydrogen triphosphate), 5-methyl-|Uridine, 5-methyl-, 5'-(tetrahydrogen triphosphate|D-rTTP|SCHEMBL625179|RZCIEJXAILMSQK-JXOAFFINSA-N|DTXSID001303289|BDShow More

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

Alternative Forms

  1. Parent:

Associated Targets(Human)

POLA1 Tclin DNA polymerase alpha subunit (225 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLB Tchem DNA polymerase beta (23632 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLG Tchem DNA polymerase gamma subunit 1 (50 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RY6 Tchem Pyrimidinergic receptor P2Y6 (717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RY4 Tchem Pyrimidinergic receptor P2Y4 (598 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RY2 Tclin Purinergic receptor P2Y2 (1109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

LM (36 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hepatitis B virus (7925 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Tk1 Thymidine kinase (94 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 498.17Molecular Weight (Monoisotopic): 497.9842AlogP: -2.19#Rotatable Bonds: 8
Polar Surface Area: 264.37Molecular Species: ACIDHBA: 12HBD: 7
#RO5 Violations: 2HBA (Lipinski): 17HBD (Lipinski): 7#RO5 Violations (Lipinski): 2
CX Acidic pKa: 0.90CX Basic pKa: CX LogP: -2.99CX LogD: -10.40
Aromatic Rings: 1Heavy Atoms: 30QED Weighted: 0.19Np 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