NP-MRD: Showing NP-Card for 2-O-a-D-Galactopyranuronosyl-L-rhamnose (NP0049574)

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Record Information

Version

2.0

Created at

2022-03-17 21:14:40 UTC

Updated at

2022-03-17 21:14:40 UTC

NP-MRD ID

NP0049574

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-O-a-D-Galactopyranuronosyl-L-rhamnose

Description

2-O-a-D-Galactopyranuronosyl-L-rhamnose, also known as aldobiouronic acid b, 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. 2-O-a-D-Galactopyranuronosyl-L-rhamnose is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-O-a-D-Galactopyranuronosyl-L-rhamnose has been detected, but not quantified in, a few different foods, such as coffee and coffee products, fats and oils, and fruits. 2-O-a-D-Galactopyranuronosyl-L-rhamnose is found in Abies amabilis. This could make 2-O-a-D-galactopyranuronosyl-L-rhamnose a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311402D          

 23 24  0  0  0  0            999 V2000
   -5.2054    2.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765    2.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4909    1.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4909    0.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765    0.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331    0.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041    0.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9199    0.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2054    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2054   -0.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9199   -0.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041   -0.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186   -0.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -0.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -1.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620    0.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475   -0.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765   -0.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4909   -0.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4909   -1.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  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
  4 10  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 19  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
 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>
NP0049574

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(O)C(OC2OC(C(O)C(O)C2O)C(O)=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O11/c1-2-3(13)5(15)9(11(20)21-2)23-12-7(17)4(14)6(16)8(22-12)10(18)19/h2-9,11-17,20H,1H3,(H,18,19)

> <INCHI_KEY>
SILSJWQOMSRYIY-UHFFFAOYSA-N

> <FORMULA>
C12H20O11

> <MOLECULAR_WEIGHT>
340.2806

> <EXACT_MASS>
340.100561482

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
30.911248971815887

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-[(2,4,5-trihydroxy-6-methyloxan-3-yl)oxy]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-2.34

> <JCHEM_LOGP>
-3.3361903589999997

> <ALOGPS_LOGS>
-0.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.273266880790525

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1784639396774574

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6124706570049137

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
66.6604

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.86e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-[(2,4,5-trihydroxy-6-methyloxan-3-yl)oxy]oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  O   UNK     0      -9.717   3.816   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -7.049   3.816   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.383   3.046   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.383   1.506   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.049   0.736   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -3.048   1.506   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.715   0.736   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.381   1.506   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -11.050   1.506   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -9.717   0.736   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.717  -0.804   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -11.050  -1.574   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.381  -1.574   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.715  -0.804   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.048  -1.574   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.048  -3.114   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -5.716   1.506   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.382   0.736   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.382  -0.804   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.716  -1.574   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -7.049  -0.804   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.383  -1.574   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.383  -3.114   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    3                                                            
CONECT    3    1    2    4                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4   21                                                       
CONECT    6    7   18                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    4    9   11                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14    7   13   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18    6   17   19                                                  
CONECT   19   15   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21    5   20   22                                                  
CONECT   22   11   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
6-Deoxy-2-O-a-D-galactopyranuronosyl-L-mannose, 9ci	HMDB
Aldobiouronic acid b	HMDB
3,4,5-Trihydroxy-6-[(2,4,5-trihydroxy-6-methyloxan-3-yl)oxy]oxane-2-carboxylate	Generator

Chemical Formula

C₁₂H₂₀O₁₁

Average Mass

340.2806 Da

Monoisotopic Mass

340.10056 Da

IUPAC Name

3,4,5-trihydroxy-6-[(2,4,5-trihydroxy-6-methyloxan-3-yl)oxy]oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-[(2,4,5-trihydroxy-6-methyloxan-3-yl)oxy]oxane-2-carboxylic acid

CAS Registry Number

6118-79-2

SMILES

CC1OC(O)C(OC2OC(C(O)C(O)C2O)C(O)=O)C(O)C1O

InChI Identifier

InChI=1S/C12H20O11/c1-2-3(13)5(15)9(11(20)21-2)23-12-7(17)4(14)6(16)8(22-12)10(18)19/h2-9,11-17,20H,1H3,(H,18,19)

InChI Key

SILSJWQOMSRYIY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies amabilis	LOTUS Database	35616633
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

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

O-glucuronide
1-o-glucuronide
Disaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Pyran
Hydroxy acid
Oxane
Hemiacetal
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	-2.3	ALOGPS
logP	-3.3	ChemAxon
logS	-0.26	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.66 m³·mol⁻¹	ChemAxon
Polarizability	30.91 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

HMDB0040159

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019866

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

73215065

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-O-a-D-Galactopyranuronosyl-L-rhamnose (NP0049574)

MOL for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)

3D MOL for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)

3D SDF for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)

3D-SDF for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)

PDB for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)

3D PDB for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)

SMILES for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)

INCHI for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)

Structure for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)

3D Structure for NP0049574 (2-O-a-D-Galactopyranuronosyl-L-rhamnose)