NP-MRD: Showing NP-Card for Ribose-1-arsenate (NP0092009)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 18:54:38 UTC

Updated at

2022-05-11 18:54:38 UTC

NP-MRD ID

NP0092009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ribose-1-arsenate

Description

Ribose-1-arsenate belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. The pathway starts with the reduction of arsenate to arsenite. Ribose-1-arsenate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ribose-1-arsenate is an intermediate in arsenate detoxification I pathway. In this process,arsenate can be conjugate to ribose by the enzyme purine nucleoside phosphorylase (PNP), which accepts arsenate as an alternative substrate to its normal substrate, phosphate. Ribose-1-arsenate exists in all living organisms, ranging from bacteria to humans. Ribose-1-arsenate can be biosynthesized from arsenate; which is catalyzed by the enzyme purine nucleoside phosphorylase. In humans, ribose-1-arsenate is involved in arsenate detoxification. Arsenic detoxification in most mammals involves alternative steps of reduction and oxidative methylation. Outside of the human body, Ribose-1-arsenate has been detected, but not quantified in, several different foods, such as cascade huckleberries, pomegranates, sapodilla, squashberries, and lindens. This could make ribose-1-arsenate a potential biomarker for the consumption of these foods. The end metabolites are methylarsonate,cacodylate, and dimethylarsinous acid,which are less reactive than arsenate and arsenite, and are excreted in the urine. The ribose-1-arsenate thus formed is converted to arsenite in the presence of dihydrolipoate, in a process that has not been fully characterized yet.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241203542D          

 14 14  0  0  0  0            999 V2000
   11.7223  -10.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4674   -9.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9518   -8.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4674   -8.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6827   -8.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2616   -8.2803    0.0000 As  0  0  0  0  0  0  0  0  0  0  0  0
   11.1702  -10.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7767   -8.8423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7223   -7.3902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9260   -7.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5972   -9.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5079   -8.6160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6827   -9.2548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0152   -7.9447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  3  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 14  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0092009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(O[As](O)(O)=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C5H11AsO8/c7-1-2-3(8)4(9)5(13-2)14-6(10,11)12/h2-5,7-9H,1H2,(H2,10,11,12)

> <INCHI_KEY>
RYJJOMQPAAUFBF-UHFFFAOYSA-N

> <FORMULA>
C5H11AsO8

> <MOLECULAR_WEIGHT>
274.0576

> <EXACT_MASS>
273.966988745

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
19.49923026237424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}arsonic acid

> <ALOGPS_LOGP>
-1.94

> <JCHEM_LOGP>
-2.5046

> <ALOGPS_LOGS>
-0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.93490792265432

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8394227440880986

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981146014940057

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
35.318599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxyarsonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      21.882 -19.216   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.406 -17.752   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.310 -16.506   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.406 -15.260   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.941 -15.736   0.000  0.00  0.00           C+0
HETATM    6 As   UNK     0      17.288 -15.457   0.000  0.00  0.00          As+0
HETATM    7  O   UNK     0      20.851 -20.360   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      23.850 -16.506   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      21.882 -13.795   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      16.662 -14.050   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      17.915 -16.863   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      15.881 -16.083   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      19.941 -17.276   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      18.695 -14.830   0.000  0.00  0.00           O+0
CONECT    1    7    2                                                       
CONECT    2    1    3   13                                                  
CONECT    3    2    8    4                                                  
CONECT    4    3    9    5                                                  
CONECT    5    4   13   14                                                  
CONECT    6   14   10   11   12                                             
CONECT    7    1                                                            
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    2    5                                                       
CONECT   14    5    6                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Ribose-1-arsenic acid	Generator

Chemical Formula

C₅H₁₁AsO₈

Average Mass

274.0576 Da

Monoisotopic Mass

273.96699 Da

IUPAC Name

{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}arsonic acid

Traditional Name

[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxyarsonic acid

CAS Registry Number

Not Available

SMILES

OCC1OC(O[As](O)(O)=O)C(O)C1O

InChI Identifier

InChI=1S/C5H11AsO8/c7-1-2-3(8)4(9)5(13-2)14-6(10,11)12/h2-5,7-9H,1H2,(H2,10,11,12)

InChI Key

RYJJOMQPAAUFBF-UHFFFAOYSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentoses

Alternative Parents

Substituents

Pentose monosaccharide
Organic arsenate
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organic metalloid salt
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic salt
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-1.9	ALOGPS
logP	-2.5	ChemAxon
logS	-0.33	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	35.32 m³·mol⁻¹	ChemAxon
Polarizability	19.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012285

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028915

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

RIBOSE-1-ARSENATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25201247

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ribose-1-arsenate (NP0092009)

MOL for NP0092009 (Ribose-1-arsenate)

3D MOL for NP0092009 (Ribose-1-arsenate)

3D SDF for NP0092009 (Ribose-1-arsenate)

3D-SDF for NP0092009 (Ribose-1-arsenate)

PDB for NP0092009 (Ribose-1-arsenate)

3D PDB for NP0092009 (Ribose-1-arsenate)

SMILES for NP0092009 (Ribose-1-arsenate)

INCHI for NP0092009 (Ribose-1-arsenate)

Structure for NP0092009 (Ribose-1-arsenate)

3D Structure for NP0092009 (Ribose-1-arsenate)