NP-MRD: Showing NP-Card for 4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid (NP0238121)

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Record Information

Version

2.0

Created at

2022-09-06 21:27:11 UTC

Updated at

2022-09-06 21:27:11 UTC

NP-MRD ID

NP0238121

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid

Description

4,5-Bis(acetyloxy)-2-methoxy-3-[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic 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. 4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid is found in Peltophorum dubium. Based on a literature review very few articles have been published on 4,5-bis(acetyloxy)-2-methoxy-3-[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062223272D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062223272D          

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   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  2  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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  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 13  2  0  0  0  0
  9 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
 16 18  2  0  0  0  0
 14 19  2  0  0  0  0
  3 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
 20 38  1  0  0  0  0
 38 39  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0238121

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=C(OC(C)=O)C(OC(C)=O)=C1[C@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O16/c1-10(27)36-9-18-22(39-13(4)30)24(40-14(5)31)25(41-15(6)32)23(42-18)19-20(35-7)16(26(33)34)8-17(37-11(2)28)21(19)38-12(3)29/h8,18,22-25H,9H2,1-7H3,(H,33,34)/t18-,22-,23-,24+,25+/m1/s1

> <INCHI_KEY>
LYLJPRYWMSIMRQ-LTWLMLOISA-N

> <FORMULA>
C26H30O16

> <MOLECULAR_WEIGHT>
598.51

> <EXACT_MASS>
598.153384886

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.61472444451135

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-bis(acetyloxy)-2-methoxy-3-[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid

> <JCHEM_LOGP>
-0.30513985666666676

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.563737774572212

> <JCHEM_PKA_STRONGEST_BASIC>
-4.165638259522894

> <JCHEM_POLAR_SURFACE_AREA>
213.55999999999997

> <JCHEM_REFRACTIVITY>
131.76650000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,5-bis(acetyloxy)-2-methoxy-3-[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14    3   20                                                  
CONECT   20   19   21   38                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33   20   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

View in JSmol

Synonyms

Value	Source
4,5-Bis(acetyloxy)-2-methoxy-3-[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoate	Generator

Chemical Formula

C₂₆H₃₀O₁₆

Average Mass

598.5100 Da

Monoisotopic Mass

598.15338 Da

IUPAC Name

4,5-bis(acetyloxy)-2-methoxy-3-[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid

Traditional Name

4,5-bis(acetyloxy)-2-methoxy-3-[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C=C(OC(C)=O)C(OC(C)=O)=C1[C@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C26H30O16/c1-10(27)36-9-18-22(39-13(4)30)24(40-14(5)31)25(41-15(6)32)23(42-18)19-20(35-7)16(26(33)34)8-17(37-11(2)28)21(19)38-12(3)29/h8,18,22-25H,9H2,1-7H3,(H,33,34)/t18-,22-,23-,24+,25+/m1/s1

InChI Key

LYLJPRYWMSIMRQ-LTWLMLOISA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Peltophorum dubium	LOTUS Database	35616633

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
C-glycosyl compound
O-methoxybenzoic acid or derivatives
Phenol ester
Benzoic acid or derivatives
Benzoic acid
Methoxybenzene
Benzoyl
Phenoxy compound
Anisole
Phenol ether
Alkyl aryl ether
Monosaccharide
Monocyclic benzene moiety
Oxane
Benzenoid
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	-0.31	ChemAxon
pKa (Strongest Acidic)	3.56	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	213.56 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	131.77 m³·mol⁻¹	ChemAxon
Polarizability	55.61 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

163024083

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid (NP0238121)

MOL for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)

3D MOL for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)

3D SDF for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)

3D-SDF for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)

PDB for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)

3D PDB for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)

SMILES for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)

INCHI for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)

Structure for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)

3D Structure for NP0238121 (4,5-bis(acetyloxy)-2-methoxy-3-[(2r,3s,4r,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]benzoic acid)