Chemistry:Adenosine thiamine triphosphate

Adenosine thiamine triphosphate

Names
Systematic IUPAC name (22R,23R,24S,25R)-16,134-Diamino-23,24,5,7,9-pentahydroxy-134,152-dimethyl-5,7,9-trioxo-4,6,8,10-tetraoxa-5λ5,7λ5,9λ5-triphospha-133λ5-1(9)-purina-15(5)-pyrimidina-13(5,3)-[1,3]thiazola-2(2,5)-oxolanapentadecaphan-133-ylium
Other names P1,P3-(Adenosine-5′-thiamine) triphosphate
Identifiers
CAS Number	30632-11-2 (chloride) Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:71394 N
ChemSpider	13082023 Y
MeSH	adenosine+thiamine+triphosphate
PubChem CID	15938962
UNII	9FE2NX8HJW Y
InChI InChI=1S/C22H30N9O13P3S/c1-11-15(48-10-30(11)6-13-5-25-12(2)29-19(13)23)3-4-40-45(34,35)43-47(38,39)44-46(36,37)41-7-14-17(32)18(33)22(42-14)31-9-28-16-20(24)26-8-27-21(16)31/h5,8-10,14,17-18,22,32-33H,3-4,6-7H2,1-2H3,(H6-,23,24,25,26,27,29,34,35,36,37,38,39)/p+1/t14-,17-,18-,22-/m1/s1 Y Key: FGOYXNBJKMNPDH-SAJUPQAESA-O Y InChI=1/C22H30N9O13P3S/c1-11-15(48-10-30(11)6-13-5-25-12(2)29-19(13)23)3-4-40-45(34,35)43-47(38,39)44-46(36,37)41-7-14-17(32)18(33)22(42-14)31-9-28-16-20(24)26-8-27-21(16)31/h5,8-10,14,17-18,22,32-33H,3-4,6-7H2,1-2H3,(H6-,23,24,25,26,27,29,34,35,36,37,38,39)/p+1/t14-,17-,18-,22-/m1/s1 Key: FGOYXNBJKMNPDH-YLNAWJOLBZ
SMILES NC1=NC=NC2=C1N=CN2[C@H]3[C@H](O)[C@H](O)[C@@H](COP(OP(OP(OCCC4=C(C)[N+](CC5=CN=C(C)N=C5N)=CS4)(O)=O)(O)=O)(O)=O)O3 O=P(O)(OC[C@H]3O[C@@H](n1c2ncnc(N)c2nc1)[C@H](O)[C@@H]3O)OP(=O)(O)OP(=O)(O)OCCc4sc[n+](c4C)Cc5c(nc(nc5)C)N
Properties
Chemical formula	C22H31N9O13P3S
Molar mass	754.52 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Tracking categories (test):

• SizeSet

Adenosine thiamine triphosphate (AThTP), or thiaminylated adenosine triphosphate, is a natural thiamine adenine nucleotide. It was discovered in Escherichia coli where it may account for up to 15 - 20% of total thiamine under carbon starvation. AThTP also exists in eukaryotic organisms such as yeast, roots of higher plants and animal tissues, albeit at a much lower concentration. It was found to exist in small amounts in the muscle, heart, brain, kidneys and liver of mice.

In E. coli AThTP is synthesized from thiamine diphosphate (ThDP) according to the following reaction catalyzed by thiamine diphosphate adenylyl transferase:

ThDP + ATP (ADP) ↔ AThTP + PP_i (P_i)

Structure and function

The molecule is made up of thiamine and adenosine joined together with phosphate groups. It is similar in structure to NAD+. The function of AThTP is not currently known but it has been shown to inhibit the activity of PARP-1.

External links

• "A first for vitamins". Nature 446 (7132): 112–113. 2007. doi:10.1038/446112a. 
• Jordan F (2007). "Adenosine triphosphate and thiamine cross paths". Nat. Chem. Biol. 3 (4): 202–3. doi:10.1038/nchembio0407-202. PMID 17372602.