ChemFOnt: Showing chemical card for Diadenosine triphosphate (CFc000000896)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:25 UTC

Chemfont ID

CFc000000896

Molecule Identification

Common Name

Diadenosine triphosphate

Definition

Diadenosine triphosphate (AP3A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP3A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP3A is synthesized in cells by tryptophanyl-tRNA synthetase (WRS); cellular level of AP3A significantly increases after interferon treatment. AP3A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP3A accumulates in cells in response to various physiological factors. AP3A FHIT (Fragile histidine Triad) is a human tumor suppressor gene. The Fhit protein is believed to inhibit tumor growth by inducing apoptosis through interaction with AP3A. (PMID: 11212966 , 12738682 , 11810214 , 9607303 , 8922753 , 9187362 , 16401072 , 12833632 , 11896678 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Diadenosine triphosphoric acid	Generator
Adenosine (5')triphospho(5')adenosine	HMDB
Adenosine 5'-triphosphate 5'-adenosine	HMDB
Adenosine(3)triphosphate adenosine	HMDB
Adenosine(5')triphospho(5')adenosine	HMDB
Bis(adenosine)-5'-triphosphate	HMDB
p(1),p(3)-Bis(5'-adenosyl) trihydrogen triphosphate	HMDB
p(1),p(3)-Bis(5'-adenosyl) triphosphate	HMDB
p(1)-p(3)-Bis(5'-adenosyl) triphosphate	HMDB
P1,P3-Bis(5'-adenosyl) triphosphate	HMDB
Ap3a	HMDB
5'Ap3a	HMDB
p(1),(P3)-Bis(5'-adenosyl)triphosphate	HMDB
ApppA	HMDB

Chemical Formula

C₂₀H₂₇N₁₀O₁₆P₃

Average Molecular Weight

756.4071

Monoisotopic Molecular Weight

756.081934402

IUPAC Name

{[(2S,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid

Traditional Name

[(2S,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphinic acid

CAS Registry Number

56432-02-1

SMILES

NC1=C2N=CN([C@H]3O[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@H](O)[C@@H]3O)C2=NC=N1

InChI Identifier

InChI=1S/C20H27N10O16P3/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(43-19)1-41-47(35,36)45-49(39,40)46-48(37,38)42-2-8-12(32)14(34)20(44-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12+,13-,14+,19-,20+

InChI Key

QCICUPZZLIQAPA-WGIMJHEJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

very long-chain fatty acid (CHEBI:42394 )
straight-chain saturated fatty acid (CHEBI:42394 )
Straight chain fatty acids (LMFA01010023 )

Functional Ontology

Physiological effect

Health effect

Intervention

Hemodialysis (HMDB: HMDB0001155)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12738682)

Source

Endogenous

Endogenous (HMDB: HMDB0001155)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Inner Membrane Transport (PathBank: SMP0121270)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.39 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-9.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.91	ChemAxon
pKa (Strongest Basic)	5.29	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	387.44 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	155.23 m³·mol⁻¹	ChemAxon
Polarizability	62.1 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0001155

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022454

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06197

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14464643

PDB ID

Not Available

ChEBI ID

27775

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Diadenosine triphosphate (CFc000000896)

MOL for CFc000000896 (Diadenosine triphosphate)

3D MOL for CFc000000896 (Diadenosine triphosphate)

3D SDF for CFc000000896 (Diadenosine triphosphate)

3D-SDF for CFc000000896 (Diadenosine triphosphate)

PDB for CFc000000896 (Diadenosine triphosphate)

3D PDB for CFc000000896 (Diadenosine triphosphate)

SMILES for CFc000000896 (Diadenosine triphosphate)

INCHI for CFc000000896 (Diadenosine triphosphate)

Structure for CFc000000896 (Diadenosine triphosphate)

3D Structure for CFc000000896 (Diadenosine triphosphate)