NP-MRD: Showing NP-Card for 4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose (NP0335804)

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Record Information

Version

2.0

Created at

2024-09-11 03:18:58 UTC

Updated at

2024-09-11 03:18:59 UTC

NP-MRD ID

NP0335804

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose

Description

4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose 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. Based on a literature review very few articles have been published on 4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262305512D          

 23 24  0  0  0  0            999 V2000
    1.1180    0.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -0.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110    0.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -0.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7399   -1.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -2.6032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -3.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1180   -3.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1180   -4.6657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -5.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -5.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2614   -3.4282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469   -3.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469   -4.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2614   -5.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -2.6032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110   -2.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110   -1.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -0.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1180   -1.3657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1180   -2.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -2.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -3.4282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4 18  1  0  0  0  0
  6  7  1  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335804

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(O)C(O)C(OC2COC(O)C(O)C2O)OC1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C12H20O11/c1-20-8-5(14)7(16)12(23-9(8)10(17)18)22-3-2-21-11(19)6(15)4(3)13/h3-9,11-16,19H,2H2,1H3,(H,17,18)

> <INCHI_KEY>
SCLWJHZCJVLFST-UHFFFAOYNA-N

> <FORMULA>
C12H20O11

> <MOLECULAR_WEIGHT>
340.281

> <EXACT_MASS>
340.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.667019397960416

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-3-methoxy-6-[(4,5,6-trihydroxyoxan-3-yl)oxy]oxane-2-carboxylic acid

> <JCHEM_LOGP>
-3.10963888

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.269783331462959

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2737867004055485

> <JCHEM_PKA_STRONGEST_BASIC>
-3.679383025321734

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
66.9928

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-3-methoxy-6-[(4,5,6-trihydroxyoxan-3-yl)oxy]oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0       2.087   0.531   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.753  -0.239   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.581   0.531   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.914  -1.779   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.248  -2.549   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.420  -4.859   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.420  -6.399   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.087  -7.169   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.087  -8.709   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.420  -9.479   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.420 -11.019   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.088  -6.399   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.754  -7.169   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.754  -8.709   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.088  -9.479   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.914  -4.859   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.581  -4.089   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.581  -2.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.753  -1.779   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.087  -2.549   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.087  -4.089   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.753  -4.859   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.753  -6.399   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2                                                            
CONECT    4    5   18                                                       
CONECT    5    4                                                            
CONECT    6    7   21                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    7   12   14                                                  
CONECT   14   10   13   15                                                  
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18   22                                                  
CONECT   18    4   17   19                                                  
CONECT   19    2   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21    6   20   22                                                  
CONECT   22   17   21   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
4-O-(4-O-Methyl-a-D-glucopyranuronosyl)-L-arabinose	Generator
4-O-(4-O-Methyl-α-D-glucopyranuronosyl)-L-arabinose	Generator

Chemical Formula

C₁₂H₂₀O₁₁

Average Mass

340.2810 Da

Monoisotopic Mass

340.10056 Da

IUPAC Name

4,5-dihydroxy-3-methoxy-6-[(4,5,6-trihydroxyoxan-3-yl)oxy]oxane-2-carboxylic acid

Traditional Name

4,5-dihydroxy-3-methoxy-6-[(4,5,6-trihydroxyoxan-3-yl)oxy]oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1C(O)C(O)C(OC2COC(O)C(O)C2O)OC1C(O)=O

InChI Identifier

InChI=1/C12H20O11/c1-20-8-5(14)7(16)12(23-9(8)10(17)18)22-3-2-21-11(19)6(15)4(3)13/h3-9,11-16,19H,2H2,1H3,(H,17,18)

InChI Key

SCLWJHZCJVLFST-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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

1-o-glucuronide
O-glucuronide
Disaccharide
Glycosyl compound
O-glycosyl compound
Pyran
Oxane
Hemiacetal
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	-3.1	ChemAxon
pKa (Strongest Acidic)	3.27	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.99 m³·mol⁻¹	ChemAxon
Polarizability	30.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

Showing NP-Card for 4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose (NP0335804)

MOL for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)

3D MOL for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)

3D SDF for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)

3D-SDF for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)

PDB for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)

3D PDB for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)

SMILES for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)

INCHI for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)

Structure for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)

3D Structure for NP0335804 (4-O-(4-O-Methyl-alpha-D-glucopyranuronosyl)-L-arabinose)