NP-MRD: Showing NP-Card for Orsellinic acid 2-O-beta-D-glucoside (NP0047084)

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Record Information

Version

2.0

Created at

2022-03-17 20:34:22 UTC

Updated at

2022-03-17 20:34:22 UTC

NP-MRD ID

NP0047084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Orsellinic acid 2-O-beta-D-glucoside

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223322D          

 23 24  0  0  0  0            999 V2000
    0.1625   -3.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0770   -2.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -0.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467   -0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467   -1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -2.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768   -3.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -1.7728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0770   -0.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8308   -0.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6536    0.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4317    0.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0526    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952    1.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171    1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962    1.1668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5890   -0.7180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308    0.3623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172    1.9778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9608    2.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5816    3.0557    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 10  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC(OC2OC(CO)C(O)C(O)C2O)=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O9/c1-5-2-6(16)3-7(9(5)13(20)21)22-14-12(19)11(18)10(17)8(4-15)23-14/h2-3,8,10-12,14-19H,4H2,1H3,(H,20,21)

> <INCHI_KEY>
AQLSLUZPCXWYQZ-UHFFFAOYSA-N

> <FORMULA>
C14H18O9

> <MOLECULAR_WEIGHT>
330.2873

> <EXACT_MASS>
330.095082174

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
30.855629420747107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.7309486233333335

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.7993655269292

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8579145388678238

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923463070615

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
74.4616

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-2-methyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic 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       0.303  -5.704   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.144  -4.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.133  -3.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.133  -1.713   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.570  -0.914   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.007  -1.713   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.007  -3.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.570  -4.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.570  -5.704   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.580  -3.309   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.144  -0.914   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.284  -0.914   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.220   0.672   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.673   0.172   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.831   1.177   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.538   2.683   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.085   3.183   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.926   2.178   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.966  -1.340   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.284   0.676   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.699   3.692   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.793   4.693   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.952   5.704   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8                                                            
CONECT   10    2                                                            
CONECT   11    4   13                                                       
CONECT   12    6                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   22                                                  
CONECT   18   13   17                                                       
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   17   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
Orsellinate 2-O-b-D-glucoside	Generator
Orsellinate 2-O-beta-D-glucoside	Generator
Orsellinate 2-O-β-D-glucoside	Generator
Orsellinic acid 2-O-b-D-glucoside	Generator
Orsellinic acid 2-O-β-D-glucoside	Generator

Chemical Formula

C₁₄H₁₈O₉

Average Mass

330.2873 Da

Monoisotopic Mass

330.09508 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(OC2OC(CO)C(O)C(O)C2O)=C1C(O)=O

InChI Identifier

InChI=1S/C14H18O9/c1-5-2-6(16)3-7(9(5)13(20)21)22-14-12(19)11(18)10(17)8(4-15)23-14/h2-3,8,10-12,14-19H,4H2,1H3,(H,20,21)

InChI Key

AQLSLUZPCXWYQZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Syzygium aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
M-cresol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Toluene
Sugar acid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-0.65	ALOGPS
logP	-0.73	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.46 m³·mol⁻¹	ChemAxon
Polarizability	30.86 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007220

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 Orsellinic acid 2-O-beta-D-glucoside (NP0047084)

MOL for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)

3D MOL for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)

3D SDF for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)

3D-SDF for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)

PDB for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)

3D PDB for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)

SMILES for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)

INCHI for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)

Structure for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)

3D Structure for NP0047084 (Orsellinic acid 2-O-beta-D-glucoside)