NP-MRD: Showing NP-Card for (-)-Glochidacuminoside A (NP0072106)

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Record Information

Version

2.0

Created at

2022-04-28 17:29:19 UTC

Updated at

2022-04-28 17:29:19 UTC

NP-MRD ID

NP0072106

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Glochidacuminoside A

Description

2-(Beta-D-Glucopyranosyloxy)benzeneacetic acid 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. (-)-Glochidacuminoside A is found in Glochidion acuminatum and Phyllanthus emblica . Based on a literature review very few articles have been published on 2-(beta-D-Glucopyranosyloxy)benzeneacetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    4.8879    0.7195    2.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9388   -0.0470    2.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8732   -0.5647    3.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9077   -0.4597    1.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9915    0.0373    0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681    0.4207   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1581    0.8887   -1.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9951    0.9798   -2.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942    0.5941   -1.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7957    0.1267   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318   -0.2711    0.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6430   -0.3202   -0.3314 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3484    0.8089    0.1093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5745    0.9236   -0.5228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3796    1.9708    0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6823    3.1757    0.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863   -0.3591   -0.7224 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9931   -0.8378   -2.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8183   -1.3761    0.2711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0511   -0.9445    1.5764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327   -1.5966    0.0345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2446   -2.4578   -1.0799 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -1.4871    4.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170   -1.5957    1.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851   -0.2283    2.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091    0.3658    0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0880    1.1952   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    1.3412   -3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811    0.6756   -2.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5289   -0.2820   -1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266    1.3993   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658    2.1322   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4961    1.6930    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2980    3.8971   -0.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -0.2280   -0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2241   -1.7959   -2.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4214   -2.2954    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9933   -0.6477    1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8709   -2.1432    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164   -3.4070   -0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 12 21  1  0
 21 22  1  0
 21 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 14  1  0
  5 10  1  0
 16 34  1  0
 15 32  1  0
 15 33  1  0
 14 31  1  6
 12 30  1  6
  9 29  1  0
  8 28  1  0
  7 27  1  0
  6 26  1  0
  4 24  1  0
  4 25  1  0
  3 23  1  0
 21 39  1  1
 22 40  1  0
 19 37  1  6
 20 38  1  0
 17 35  1  6
 18 36  1  0
M  END


  Mrv1652304282219292D          

 22 23  0  0  1  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  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
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  1  0  0  0
 14 21  1  6  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072106

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=CC=C2CC(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O8/c15-6-9-11(18)12(19)13(20)14(22-9)21-8-4-2-1-3-7(8)5-10(16)17/h1-4,9,11-15,18-20H,5-6H2,(H,16,17)/t9-,11-,12+,13-,14-/m1/s1

> <INCHI_KEY>
XEYDWXMYBFXGFT-RGCYKPLRSA-N

> <FORMULA>
C14H18O8

> <MOLECULAR_WEIGHT>
314.29

> <EXACT_MASS>
314.10016754

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.972788377196512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)acetic acid

> <ALOGPS_LOGP>
-0.83

> <JCHEM_LOGP>
-0.9606393096666661

> <ALOGPS_LOGS>
-1.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.200128787195162

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7330897989169793

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092344868096

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
71.4909

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   14   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
2-(b-D-Glucopyranosyloxy)benzeneacetate	Generator
2-(b-D-Glucopyranosyloxy)benzeneacetic acid	Generator
2-(beta-D-Glucopyranosyloxy)benzeneacetate	Generator
2-(Β-D-glucopyranosyloxy)benzeneacetate	Generator
2-(Β-D-glucopyranosyloxy)benzeneacetic acid	Generator

Chemical Formula

C₁₄H₁₈O₈

Average Mass

314.2900 Da

Monoisotopic Mass

314.10017 Da

IUPAC Name

2-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)acetic acid

Traditional Name

(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)acetic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=CC=C2CC(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C14H18O8/c15-6-9-11(18)12(19)13(20)14(22-9)21-8-4-2-1-3-7(8)5-10(16)17/h1-4,9,11-15,18-20H,5-6H2,(H,16,17)/t9-,11-,12+,13-,14-/m1/s1

InChI Key

XEYDWXMYBFXGFT-RGCYKPLRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Glochidion acuminatum	Plant	KNApSAcK
Phyllanthus emblica	Plant	KNApSAcK

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
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Polyol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
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	-0.83	ALOGPS
logP	-0.96	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.49 m³·mol⁻¹	ChemAxon
Polarizability	29.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

9155134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10979933

PDB ID

Not Available

ChEBI ID

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Good Scents ID

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References

General References

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Showing NP-Card for (-)-Glochidacuminoside A (NP0072106)

MOL for NP0072106 ((-)-Glochidacuminoside A)

3D MOL for NP0072106 ((-)-Glochidacuminoside A)

3D SDF for NP0072106 ((-)-Glochidacuminoside A)

3D-SDF for NP0072106 ((-)-Glochidacuminoside A)

PDB for NP0072106 ((-)-Glochidacuminoside A)

3D PDB for NP0072106 ((-)-Glochidacuminoside A)

SMILES for NP0072106 ((-)-Glochidacuminoside A)

INCHI for NP0072106 ((-)-Glochidacuminoside A)

Structure for NP0072106 ((-)-Glochidacuminoside A)

3D Structure for NP0072106 ((-)-Glochidacuminoside A)