NP-MRD: Showing NP-Card for 6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0271077)

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Record Information

Version

2.0

Created at

2022-09-08 17:14:41 UTC

Updated at

2022-09-08 17:14:41 UTC

NP-MRD ID

NP0271077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Description

4-[(6-Carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. 6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid is found in Rhizobium leguminosarum. 4-[(6-Carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161516202D          

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 38 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004161516202D          

 40 42  0  0  0  0            999 V2000
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    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098   -0.2428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -0.7315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 22 36  1  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  0  0  0  0
 19 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(OC1OC(C(O)C(O)C1O)C(O)=O)C1OC(O)(CC(OC2OC(C(O)C(O)C2O)C(O)=O)C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O20/c21-2-4(37-18-11(28)7(24)9(26)14(39-18)16(31)32)12-5(22)3(1-20(35,40-12)19(33)34)36-17-10(27)6(23)8(25)13(38-17)15(29)30/h3-14,17-18,21-28,35H,1-2H2,(H,29,30)(H,31,32)(H,33,34)

> <INCHI_KEY>
BWYSMVCAOJRVCX-UHFFFAOYSA-N

> <FORMULA>
C20H30O20

> <MOLECULAR_WEIGHT>
590.44

> <EXACT_MASS>
590.133043366

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.08456741939294

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(1-{6-carboxy-4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,6-dihydroxyoxan-2-yl}-2-hydroxyethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
-1.99

> <JCHEM_LOGP>
-5.546689598666667

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.9922734926308094

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4103337810453627

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9483816667067053

> <JCHEM_POLAR_SURFACE_AREA>
340.12

> <JCHEM_REFRACTIVITY>
111.279

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.67e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(1-{6-carboxy-4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,6-dihydroxyoxan-2-yl}-2-hydroxyethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.851  -3.347   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.861  -1.633   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.872  -0.453   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       7.378  -1.365   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12                                                            
CONECT   14    7   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    3   18   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   38                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   36                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31                                                            
CONECT   33   26   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   22   17   37                                                  
CONECT   37   36                                                            
CONECT   38   19   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Value	Source
4-[(6-Carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₀H₃₀O₂₀

Average Mass

590.4400 Da

Monoisotopic Mass

590.13304 Da

IUPAC Name

6-(1-{6-carboxy-4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,6-dihydroxyoxan-2-yl}-2-hydroxyethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-(1-{6-carboxy-4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,6-dihydroxyoxan-2-yl}-2-hydroxyethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OCC(OC1OC(C(O)C(O)C1O)C(O)=O)C1OC(O)(CC(OC2OC(C(O)C(O)C2O)C(O)=O)C1O)C(O)=O

InChI Identifier

InChI=1S/C20H30O20/c21-2-4(37-18-11(28)7(24)9(26)14(39-18)16(31)32)12-5(22)3(1-20(35,40-12)19(33)34)36-17-10(27)6(23)8(25)13(38-17)15(29)30/h3-14,17-18,21-28,35H,1-2H2,(H,29,30)(H,31,32)(H,33,34)

InChI Key

BWYSMVCAOJRVCX-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Rhizobium leguminosarum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

C-glucuronide
1-o-glucuronide
O-glucuronide
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Pyran
Oxane
Hemiacetal
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Alcohol
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Organic oxide
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	-2	ALOGPS
logP	-5.5	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	2.41	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	340.12 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	111.28 m³·mol⁻¹	ChemAxon
Polarizability	51.08 Å³	ChemAxon
Number of Rings	3	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0271077)

MOL for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for NP0271077 (6-[(2-carboxy-6-{1-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-hydroxyethyl}-2,5-dihydroxyoxan-4-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)