NP-MRD: Showing NP-Card for D-Erythroascorbic acid 1'-a-D-glucoside (NP0047685)

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Record Information

Version

2.0

Created at

2022-03-17 20:44:15 UTC

Updated at

2022-03-17 20:44:15 UTC

NP-MRD ID

NP0047685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

D-Erythroascorbic acid 1'-a-D-glucoside

Description

D-Erythroascorbic acid 1'-a-D-glucoside belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. D-Erythroascorbic acid 1'-a-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, D-Erythroascorbic acid 1'-a-D-glucoside has been detected, but not quantified in, mushrooms. D-Erythroascorbic acid 1'-a-D-glucoside is found in Sclerotinia sclerotiorum. This could make D-erythroascorbic acid 1'-a-D-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307142D          

 21 22  0  0  0  0            999 V2000
    6.2895    3.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810    4.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6764    3.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964    4.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8480    4.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2349    5.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    4.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4502    4.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2787    4.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0742    3.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6326    4.9413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.5286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4064    6.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0231    4.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8372    5.5355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315    2.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4941    3.9216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    3.4340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8918    3.6245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  1  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  2  0  0  0  0
 19  2  1  0  0  0  0
 19 11  1  0  0  0  0
 20  4  1  0  0  0  0
 20 10  1  0  0  0  0
 21  3  1  0  0  0  0
 21 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCC2OC(=O)C(O)=C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O10/c12-1-3-5(13)7(15)9(17)11(21-3)19-2-4-6(14)8(16)10(18)20-4/h3-5,7,9,11-17H,1-2H2

> <INCHI_KEY>
VMBZDIQDNQIPAL-UHFFFAOYSA-N

> <FORMULA>
C11H16O10

> <MOLECULAR_WEIGHT>
308.2387

> <EXACT_MASS>
308.074346732

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
27.731535981225594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydroxy-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
-2.34

> <JCHEM_LOGP>
-3.0540595793333334

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.051114873550075

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.452430439078072

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834237611594

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
63.48290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.94e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5H-furan-2-one

> <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  C   UNK     0      11.740   6.211   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.378   8.351   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.596   7.242   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.913   7.875   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.916   8.748   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   8.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.772   9.778   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.421   7.875   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.307   9.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.897   6.410   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.987   7.796   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.205   6.687   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      12.381   9.224   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667  10.320   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.092  11.285   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.043   8.351   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.163  10.333   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.992   5.164   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.522   7.320   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.437   6.410   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.131   6.766   0.000  0.00  0.00           O+0
CONECT    1    3   12                                                       
CONECT    2    4   19                                                       
CONECT    3    1    5   21                                                  
CONECT    4    2    6   20                                                  
CONECT    5    3    7   13                                                  
CONECT    6    4    8   14                                                  
CONECT    7    5    9   15                                                  
CONECT    8    6   10   16                                                  
CONECT    9    7   11   17                                                  
CONECT   10    8   18   20                                                  
CONECT   11    9   19   21                                                  
CONECT   12    1                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19    2   11                                                       
CONECT   20    4   10                                                       
CONECT   21    3   11                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
D-Erythroascorbate 1'-a-D-glucoside	Generator

Chemical Formula

C₁₁H₁₆O₁₀

Average Mass

308.2387 Da

Monoisotopic Mass

308.07435 Da

IUPAC Name

3,4-dihydroxy-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,5-dihydrofuran-2-one

Traditional Name

3,4-dihydroxy-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5H-furan-2-one

CAS Registry Number

174339-86-7

SMILES

OCC1OC(OCC2OC(=O)C(O)=C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C11H16O10/c12-1-3-5(13)7(15)9(17)11(21-3)19-2-4-6(14)8(16)10(18)20-4/h3-5,7,9,11-17H,1-2H2

InChI Key

VMBZDIQDNQIPAL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Sclerotinia sclerotiorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
2-furanone
Monosaccharide
Oxane
Dihydrofuran
Vinylogous acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Enediol
Carboxylic acid ester
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Carbonyl group
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	-2.3	ALOGPS
logP	-3.1	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	63.48 m³·mol⁻¹	ChemAxon
Polarizability	27.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033627

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011716

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

131751466

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for D-Erythroascorbic acid 1'-a-D-glucoside (NP0047685)

MOL for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)

3D MOL for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)

3D SDF for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)

3D-SDF for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)

PDB for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)

3D PDB for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)

SMILES for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)

INCHI for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)

Structure for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)

3D Structure for NP0047685 (D-Erythroascorbic acid 1'-a-D-glucoside)