Showing Compound P1,P4-bis(5'-guanosyl) tetraphosphate (FDB031082)

Record Information

Version

1.0

Creation date

2015-05-07 20:58:27 UTC

Update date

2019-11-26 03:22:08 UTC

Primary ID

FDB031082

Secondary Accession Numbers

FDB022564

Chemical Information

FooDB Name

P1,P4-bis(5'-guanosyl) tetraphosphate

Description

P(1),p(4)-bis(5'-guanosyl) tetraphosphate, also known as gp4g or gppppg, is a member of the class of compounds known as (5'->5')-dinucleotides (5'->5')-dinucleotides are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. P(1),p(4)-bis(5'-guanosyl) tetraphosphate is soluble (in water) and an extremely strong acidic compound (based on its pKa). P(1),p(4)-bis(5'-guanosyl) tetraphosphate can be found in a number of food items such as allium (onion), pasta, rocket salad (sspecies), and vanilla, which makes p(1),p(4)-bis(5'-guanosyl) tetraphosphate a potential biomarker for the consumption of these food products. P(1),p(4)-bis(5'-guanosyl) tetraphosphate exists in all living species, ranging from bacteria to humans. In humans, p(1),p(4)-bis(5'-guanosyl) tetraphosphate is involved in few metabolic pathways, which include azathioprine action pathway, mercaptopurine action pathway, purine metabolism, and thioguanine action pathway. P(1),p(4)-bis(5'-guanosyl) tetraphosphate is also involved in several metabolic disorders, some of which include lesch-nyhan syndrome (LNS), myoadenylate deaminase deficiency, mitochondrial DNA depletion syndrome, and xanthine dehydrogenase deficiency (xanthinuria).

CAS Number

4130-19-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(PPG)2	ChEBI
[5-(2-Amino-6-hydroxy-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[[[[5-(2-amino-6-hydroxy-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-phosphinic acid	HMDB
Bis(5'-guanosyl) tetraphosphate	ChEBI
Bis(5'-guanosyl) tetraphosphoric acid	Generator
Bis(guanylyl) diphosphate	ChEBI
Bis(guanylyl) diphosphoric acid	Generator
Diguanosine tetraphosphoric acid	Generator
g(5')P4(5')g	ChEBI
GP4g	ChEBI
GPPPPG	ChEBI

Showing 1 to 10 of 13 entries

Predicted Properties

Property	Value	Source
Water Solubility	11 g/L	ALOGPS
logP	-0.18	ALOGPS
logP	-5.9	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	0.5	ChemAxon
pKa (Strongest Basic)	1.6	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	465.33 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	168.95 m³·mol⁻¹	ChemAxon
Polarizability	68.35 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

C20H28N10O21P4

IUPAC name

{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid

InChI Identifier

InChI=1S/C20H28N10O21P4/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(47-17)1-45-52(37,38)49-54(41,42)51-55(43,44)50-53(39,40)46-2-6-10(32)12(34)18(48-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1

InChI Key

OLGWXCQXRSSQPO-MHARETSRSA-N

Isomeric SMILES

NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=C(N)NC4=O)[C@@H](O)[C@H]2O)C(=O)N1

Average Molecular Weight

868.3858

Monoisotopic Molecular Weight

868.038094056

Classification

Description

Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

(5'->5')-dinucleotides

Sub Class

Not Available

Direct Parent

(5'->5')-dinucleotides

Alternative Parents

Substituents

(5'->5')-dinucleotide
Purine ribonucleoside polyphosphate
Purine nucleotide sugar
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Imidazopyrimidine
Purine
Pyrimidone
Monoalkyl phosphate
Aminopyrimidine
Pyrimidine
Alkyl phosphate
Phosphoric acid ester
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Tetrahydrofuran
Vinylogous amide
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Organic nitrogen compound
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanosine 5'-phosphate (CHEBI:15883 )
purine ribonucleoside 5'-tetraphosphate (CHEBI:15883 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Animal

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
EI-MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0910110030-a6bd659122b84da65d3f	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-c04b5e08bc949915c2fd	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0900000000-de8f07c2ed0e9f17f0ee	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-0700011090-f69c78a4b50e25f0eb5c	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900010000-b766f54c386c57ea4bcd	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-2915010000-506add7a25f1233ab648	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000020-b1759ae61121c874c253	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000020-ad098ec0ac59f44f6bc6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-0900100000-91fc747e55e03728ef79	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000090-cb93d23c88ced7dae5b0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gb9-0400020390-175e627e05080096994a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pbc-0510390050-039fd4c9138a3432cc17	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

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

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound P1,P4-bis(5'-guanosyl) tetraphosphate (FDB031082)

Structure for FDB031082 (P1,P4-bis(5'-guanosyl) tetraphosphate)