CHEBI:44672 - 3'-phosphate-adenosine-5'-diphosphate

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ChEBI Name 3'-phosphate-adenosine-5'-diphosphate
ChEBI ID CHEBI:44672
Definition An adenosine 3'-phosphate that is ADP carrying a phospate group at the 3'-position. It is potent inhibitor of bovine pancreatic ribonuclease A.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000013527438
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Formula C10H16N5O13P3
Net Charge 0
Average Mass 507.181
Monoisotopic Mass 506.99575
InChI InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-31(23,24)28-30(20,21)22/h2-4,6-7,10,16H,1H2,(H,23,24)(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1
InChIKey GBBWIZKLHXYJOA-KQYNXXCUSA-N
SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O
ChEBI Ontology
Outgoing 3'-phosphate-adenosine-5'-diphosphate (CHEBI:44672) has functional parent ADP (CHEBI:16761)
3'-phosphate-adenosine-5'-diphosphate (CHEBI:44672) is a adenosine 3'-phosphate (CHEBI:37097)
3'-phosphate-adenosine-5'-diphosphate (CHEBI:44672) is a adenosine 5'-phosphate (CHEBI:37096)
Incoming coenzyme A (CHEBI:15346) has functional parent 3'-phosphate-adenosine-5'-diphosphate (CHEBI:44672)
IUPAC Name
adenosine 3'-(dihydrogen phosphate) 5'-(trihydrogen diphosphate)
Synonyms Sources
5'-diphosphoadenosine 3'-phosphate ChEBI
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-oxolan-2-yl]methyl phosphono hydrogen phosphate PDBeChem
adenosine 3'-phosphate 5'-diphosphate ChEBI
Manual Xref Database
PAP PDBeChem
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Registry Number Type Source
13400-10-7 CAS Registry Number ChEBI
Citations
Leonidas DD, Shapiro R, Irons LI, Russo N, Acharya KR (1999)
Toward rational design of ribonuclease inhibitors: high-resolution crystal structure of a ribonuclease A complex with a potent 3',5'-pyrophosphate-linked dinucleotide inhibitor.
Biochemistry 38, 10287-10297 [PubMed:10441122]
[show Abstract]
Russo N, Shapiro R (1999)
Potent inhibition of mammalian ribonucleases by 3', 5'-pyrophosphate-linked nucleotides.
The Journal of biological chemistry 274, 14902-14908 [PubMed:10329690]
[show Abstract]
Russo N, Shapiro R, Vallee BL (1997)
5'-Diphosphoadenosine 3'-phosphate is a potent inhibitor of bovine pancreatic ribonuclease A.
Biochemical and biophysical research communications 231, 671-674 [PubMed:9070868]
[show Abstract]
Leonidas DD, Shapiro R, Irons LI, Russo N, Acharya KR (1997)
Crystal structures of ribonuclease A complexes with 5'-diphosphoadenosine 3'-phosphate and 5'-diphosphoadenosine 2'-phosphate at 1.7 A resolution.
Biochemistry 36, 5578-5588 [PubMed:9154942]
[show Abstract]
Fierke CA, Jencks WP (1986)
Two functional domains of coenzyme A activate catalysis by coenzyme A transferase. Pantetheine and adenosine 3'-phosphate 5'-diphosphate.
The Journal of biological chemistry 261, 7603-7606 [PubMed:3458707]
[show Abstract]
Last Modified
03 June 2024