Showing Compound Diadenosine triphosphate (FDB022454)

Record Information

Version

1.0

Creation date

2011-09-21 00:14:17 UTC

Update date

2015-07-21 06:57:13 UTC

Primary ID

FDB022454

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Diadenosine triphosphate

Description

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) [HMDB]

CAS Number

56432-02-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
5'Ap3a	HMDB
Adenosine (5')trio(5')adenosine	HMDB
Adenosine (5')triphospho(5')adenosine	HMDB
Adenosine 5'-triate 5'-adenosine	HMDB
Adenosine 5'-triphosphate 5'-adenosine	HMDB
Adenosine(3)triate adenosine	HMDB
Adenosine(3)triphosphate adenosine	HMDB
Adenosine(5')trio(5')adenosine	HMDB
Adenosine(5')triphospho(5')adenosine	HMDB
adenosine(5')triphospho(5')adenosine	hmdb

Showing 1 to 10 of 28 entries

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

Chemical Formula

C20H27N10O16P3

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

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

Isomeric 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

Average Molecular Weight

756.4071

Monoisotopic Molecular Weight

756.081934402

Classification

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 )

Ontology

Physiological effect

Health effect:

Health condition:

Hemodialysis

Disposition

Biological location:

Biofluid and excreta:

Blood

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Diadenosine triphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-1211090100-8dd4ac3e3f704ce81480	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TBDMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TBDMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TBDMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diadenosine triphosphate, TBDMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0910100300-a4645b9f9e4bff03904a	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-9d576618c3405dd82c62	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-d874a1705ef911a68a3f	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a59-0700110900-6003bb661e58b16c00f0	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900100000-cc9f72dc9a076e69680c	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001r-1940100000-375a011d350537091bbb	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000900-6de9f94edaaf63b06abb	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1302302900-67b889b6aeb6c6b75d7f	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0600901100-01ba1d8c1675b37b46f0	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0100000900-f690574ac6b3670ec7c6	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0300003900-7ccaa7c6ba1c635f1660	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0901010000-452975aa0aa202f669c0	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C06197

Pubchem Compound ID

14464643

Pubchem Substance ID

Not Available

ChEBI ID

27775

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01155

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Diadenosine triphosphate (FDB022454)

Structure for FDB022454 (Diadenosine triphosphate)