NP-MRD: Showing NP-Card for (R)-Pantothenic acid 4'-O-b-D-glucoside (NP0047802)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:13 UTC

Updated at

2022-03-17 20:46:13 UTC

NP-MRD ID

NP0047802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-Pantothenic acid 4'-O-b-D-glucoside

Description

(R)-Pantothenic acid 4'-O-b-D-glucoside belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol (R)-Pantothenic acid 4'-O-b-D-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (R)-Pantothenic acid 4'-O-b-D-glucoside has been detected, but not quantified in, garden tomato. This could make (R)-pantothenic acid 4'-O-b-D-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241220052D          

 26 26  0  0  0  0            999 V2000
    4.2703   -0.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938    0.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420   -0.5820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091    1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    1.3585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    1.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515   -0.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503   -1.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1738   -1.9797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703   -0.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714    0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703    0.9702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -0.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    1.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8538    0.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110    1.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549    1.9797    0.0000 C   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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  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
 18 19  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv0541 02241220052D          

 26 26  0  0  0  0            999 V2000
    4.2703   -0.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938    0.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420   -0.5820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091    1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    1.3585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503    1.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515   -0.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503   -0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9503   -1.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1738   -1.9797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703   -0.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714    0.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703    0.9702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557   -0.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    1.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8538    0.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110    1.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549    1.9797    0.0000 C   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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  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
 18 19  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(COC1OC(CO)C(O)C(O)C1O)C(O)C(=O)NCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H27NO10/c1-15(2,12(23)13(24)16-4-3-8(18)19)6-25-14-11(22)10(21)9(20)7(5-17)26-14/h7,9-12,14,17,20-23H,3-6H2,1-2H3,(H,16,24)(H,18,19)

> <INCHI_KEY>
GMURXYJSTRMISD-UHFFFAOYSA-N

> <FORMULA>
C15H27NO10

> <MOLECULAR_WEIGHT>
381.3756

> <EXACT_MASS>
381.163496089

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
36.901764013465794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-hydroxy-3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanamido)propanoic acid

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-3.126210752333333

> <ALOGPS_LOGS>
-0.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.085294377753897

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.212405387065977

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834130970276

> <JCHEM_POLAR_SURFACE_AREA>
186.01

> <JCHEM_REFRACTIVITY>
83.9244

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.66e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-hydroxy-3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanamido)propanoic 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  O   UNK     0       7.971  -1.086   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.522  -0.362   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.522   1.376   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.217  -1.086   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.768  -0.362   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.318  -1.086   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.884   3.116   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.333   2.536   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.203   1.086   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.507   1.811   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.507   3.261   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.203  -0.362   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.507  -1.086   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.507  -2.536   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.058  -3.695   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -7.971  -1.086   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.667  -0.362   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.667   1.086   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.971   1.811   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.291  -1.376   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.869  -0.362   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.869   1.376   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.318   2.101   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.594   0.941   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.581   2.101   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.289   3.695   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   21                                                       
CONECT    7    8   25                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   13   16   18                                                  
CONECT   18   10   17   19                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21    6   20   22                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25    7   22   24   26                                             
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

Value	Source
(R)-Pantothenate 4'-O-b-D-glucoside	Generator
3-[(1,2-Dihydroxy-3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butylidene)amino]propanoate	Generator

Chemical Formula

C₁₅H₂₇NO₁₀

Average Mass

381.3756 Da

Monoisotopic Mass

381.16350 Da

IUPAC Name

3-(2-hydroxy-3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanamido)propanoic acid

Traditional Name

3-(2-hydroxy-3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanamido)propanoic acid

CAS Registry Number

29493-59-2

SMILES

CC(C)(COC1OC(CO)C(O)C(O)C1O)C(O)C(=O)NCCC(O)=O

InChI Identifier

InChI=1S/C15H27NO10/c1-15(2,12(23)13(24)16-4-3-8(18)19)6-25-14-11(22)10(21)9(20)7(5-17)26-14/h7,9-12,14,17,20-23H,3-6H2,1-2H3,(H,16,24)(H,18,19)

InChI Key

GMURXYJSTRMISD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solanum lycopersicum	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 fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Secondary alcohol
Acetal
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Polyol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Primary alcohol
Organic oxygen compound
Organopnictogen compound
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	-1.7	ALOGPS
logP	-3.1	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.01 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	83.92 m³·mol⁻¹	ChemAxon
Polarizability	36.9 Å³	ChemAxon
Number of Rings	1	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

HMDB0033965

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012194

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

14132229

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (R)-Pantothenic acid 4'-O-b-D-glucoside (NP0047802)

MOL for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)

3D MOL for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)

3D SDF for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)

3D-SDF for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)

PDB for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)

3D PDB for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)

SMILES for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)

INCHI for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)

Structure for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)

3D Structure for NP0047802 ((R)-Pantothenic acid 4'-O-b-D-glucoside)