NP-MRD: Showing NP-Card for ADP-glucose (NP0044305)

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Record Information

Version

1.0

Created at

2022-02-14 20:48:20 UTC

Updated at

2022-03-10 22:17:52 UTC

NP-MRD ID

NP0044305

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ADP-glucose

Description

ADP-glucose, also known as ADPG or ADP-a-D-glucose, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. ADP-glucose is a strong basic compound (based on its pKa). ADP-glucose exists in all living organisms, ranging from bacteria to humans. In humans, ADP-glucose is involved in ticlopidine metabolism pathway. ADP-glucose is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042000322D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042000322D          

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M  END
> <DATABASE_ID>
NP0044305

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H]3O)C2=NC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/t5-,6-,8-,9-,10+,11-,12-,15-,16-/m1/s1

> <INCHI_KEY>
WFPZSXYXPSUOPY-ROYWQJLOSA-N

> <FORMULA>
C16H25N5O15P2

> <MOLECULAR_WEIGHT>
589.3417

> <EXACT_MASS>
589.082238179

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.68525373620978

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.76

> <JCHEM_LOGP>
-6.7725679530330645

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.107282857130618

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7298676687415737

> <JCHEM_PKA_STRONGEST_BASIC>
3.9931246302818533

> <JCHEM_POLAR_SURFACE_AREA>
311.74999999999994

> <JCHEM_REFRACTIVITY>
117.08579999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adp glucose

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8661.2638662.626   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8664.6038662.611   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8665.5548666.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8666.8878665.312   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0    8668.2208666.080   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0    8669.9258665.106   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0    8671.6308666.084   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0    8672.9628665.320   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8675.6268669.937   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8676.9598670.704   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8675.6268663.780   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8678.2988665.320   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8678.2988668.397   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8670.8578667.424   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8672.3968667.424   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8667.4508667.416   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8668.9898667.416   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8675.6298668.396   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8674.2958667.626   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8674.2958666.085   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8675.6298665.316   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8676.9638666.085   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8676.9638667.626   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8662.9678666.234   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8662.1978663.864   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8663.7378663.864   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8664.2128665.329   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8657.9528666.608   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8656.4468666.288   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0    8655.9708664.823   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0    8657.0008663.679   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0    8658.5078663.999   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0    8658.9838665.463   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0    8660.3898666.090   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0    8660.2298667.621   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0    8658.7228667.941   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0    8655.4158667.432   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0    8661.7238665.319   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   26                                                            
CONECT    3    4   27                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16   17                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   14   15                                             
CONECT    8    7   20                                                       
CONECT    9   10   18                                                       
CONECT   10    9                                                            
CONECT   11   21                                                            
CONECT   12   22                                                            
CONECT   13   23                                                            
CONECT   14    7                                                            
CONECT   15    7                                                            
CONECT   16    5                                                            
CONECT   17    5                                                            
CONECT   18   23   19    9                                                  
CONECT   19   18   20                                                       
CONECT   20   21   19    8                                                  
CONECT   21   20   22   11                                                  
CONECT   22   21   23   12                                                  
CONECT   23   18   22   13                                                  
CONECT   24   27   38                                                       
CONECT   25   26    1   38                                                  
CONECT   26   25   27    2                                                  
CONECT   27   26   24    3                                                  
CONECT   28   29   33   36                                                  
CONECT   29   28   37   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   28   34   32                                                  
CONECT   34   35   33   38                                                  
CONECT   35   36   34                                                       
CONECT   36   35   28                                                       
CONECT   37   29                                                            
CONECT   38   34   25   24                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
Adenosine diphosphate glucose	ChEBI
Adenosine diphosphoglucose	ChEBI
Adenosine pyrophosphateglucose	ChEBI
ADPG	ChEBI
ADPglucose	ChEBI
ADP-alpha-D-Glucose	Kegg
Adenosine diphosphoric acid glucose	Generator
ADP-a-D-Glucose	Generator
ADP-Α-D-glucose	Generator
Adenosine 5'-(trihydrogen diphosphate) glucopyranosyl ester	HMDB
Adenosine 5'-(trihydrogen diphosphate) p'-alpha-delta-glucopyranosyl ester	HMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-D-glucosyl ester	HMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-delta-glucosyl ester	HMDB
Adenosine 5'-diphosphoglucose	HMDB
Adenosine 5'-pyrophosphate a-delta-glucosyl ester	HMDB
Adenosine 5'-pyrophosphate alpha-D-glucosyl ester	HMDB
Adenosine 5'-pyrophosphate alpha-delta-glucosyl ester	HMDB
Adenosine 5'-pyrophosphate glucosyl ester	HMDB
Adenosine 5'-pyrophosphate mono-D-glucosyl ester	HMDB
Adenosine 5'-pyrophosphate mono-delta-glucosyl ester	HMDB
Adenosine diphosphate D-glucose	HMDB
Adenosine pyrophosphate-glucose	HMDB
Adenosine-5'-diphosphate-glucose	HMDB
ADP-D-Glucose	HMDB
ADP Glucose	HMDB
Diphosphate glucose, adenosine	HMDB
Diphosphoglucose, adenosine	HMDB
Glucose, ADP	HMDB
Glucose, adenosine diphosphate	HMDB
Pyrophosphateglucose, adenosine	HMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-alpha-D-glucosyl ester	HMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-α-D-glucosyl ester	HMDB
Adenosine 5’-(trihydrogen pyrophosphate) mono-D-glucosyl ester	HMDB
Adenosine 5’-(trihydrogen pyrophosphate) mono-α-D-glucosyl ester	HMDB
Adenosine 5’-diphosphoglucose	HMDB
Adenosine 5’-pyrophosphate mono-D-glucosyl ester	HMDB
ADP-Glucose	HMDB

Chemical Formula

C₁₆H₂₅N₅O₁₅P₂

Average Mass

589.3417 Da

Monoisotopic Mass

589.08224 Da

IUPAC Name

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

Traditional Name

adp glucose

CAS Registry Number

10128-35-5

SMILES

NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H]3O)C2=NC=N1

InChI Identifier

InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/t5-,6-,8-,9-,10+,11-,12-,15-,16-/m1/s1

InChI Key

WFPZSXYXPSUOPY-ROYWQJLOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	Plant	KNApSAcK
Cannabis sativa	CannabisDB	Not Available
Escherichia coli	Bacteria	KNApSAcK
Oryza sativa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Imidolactam
Alkyl phosphate
Pyrimidine
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Polyol
Oxacycle
Organic oxide
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Amine
Organonitrogen compound
Primary alcohol
Primary amine
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alpha-D-glucoside (CHEBI:15751 )
ADP-aldose (CHEBI:15751 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-6.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	3.99	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	311.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.09 m³·mol⁻¹	ChemAxon
Polarizability	48.69 Å³	ChemAxon
Number of Rings	4	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

HMDB0006557

DrugBank ID

DB01774

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16500

PDB ID

Not Available

ChEBI ID

15751

Good Scents ID

Not Available

References

General References

Munoz FJ, Baroja-Fernandez E, Moran-Zorzano MT, Viale AM, Etxeberria E, Alonso-Casajus N, Pozueta-Romero J: Sucrose synthase controls both intracellular ADP glucose levels and transitory starch biosynthesis in source leaves. Plant Cell Physiol. 2005 Aug;46(8):1366-76. doi: 10.1093/pcp/pci148. Epub 2005 Jun 11. [PubMed:15951568 ]
Li J, Baroja-Fernandez E, Bahaji A, Munoz FJ, Ovecka M, Montero M, Sesma MT, Alonso-Casajus N, Almagro G, Sanchez-Lopez AM, Hidalgo M, Zamarbide M, Pozueta-Romero J: Enhancing sucrose synthase activity results in increased levels of starch and ADP-glucose in maize (Zea mays L.) seed endosperms. Plant Cell Physiol. 2013 Feb;54(2):282-94. doi: 10.1093/pcp/pcs180. Epub 2013 Jan 3. [PubMed:23292602 ]
Rahimpour M, Montero M, Almagro G, Viale AM, Sevilla A, Canovas M, Munoz FJ, Baroja-Fernandez E, Bahaji A, Eydallin G, Dose H, Takeuchi R, Mori H, Pozueta-Romero J: GlgS, described previously as a glycogen synthesis control protein, negatively regulates motility and biofilm formation in Escherichia coli. Biochem J. 2013 Jun 15;452(3):559-73. doi: 10.1042/BJ20130154. [PubMed:23537328 ]
Coello P, Martinez-Barajas E: SnRK1 is differentially regulated in the cotyledon and embryo axe of bean (Phaseolus vulgaris L) seeds. Plant Physiol Biochem. 2014 Jul;80:153-9. doi: 10.1016/j.plaphy.2014.03.033. Epub 2014 Apr 13. [PubMed:24762788 ]
Bahaji A, Baroja-Fernandez E, Sanchez-Lopez AM, Munoz FJ, Li J, Almagro G, Montero M, Pujol P, Galarza R, Kaneko K, Oikawa K, Wada K, Mitsui T, Pozueta-Romero J: HPLC-MS/MS analyses show that the near-Starchless aps1 and pgm leaves accumulate wild type levels of ADPglucose: further evidence for the occurrence of important ADPglucose biosynthetic pathway(s) alternative to the pPGI-pPGM-AGP pathway. PLoS One. 2014 Aug 18;9(8):e104997. doi: 10.1371/journal.pone.0104997. eCollection 2014. [PubMed:25133777 ]

Showing NP-Card for ADP-glucose (NP0044305)

MOL for NP0044305 (ADP-glucose)

3D MOL for NP0044305 (ADP-glucose)

3D SDF for NP0044305 (ADP-glucose)

3D-SDF for NP0044305 (ADP-glucose)

PDB for NP0044305 (ADP-glucose)

3D PDB for NP0044305 (ADP-glucose)

SMILES for NP0044305 (ADP-glucose)

INCHI for NP0044305 (ADP-glucose)

Structure for NP0044305 (ADP-glucose)

3D Structure for NP0044305 (ADP-glucose)