NP-MRD: Showing NP-Card for 2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one (NP0261356)

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Record Information

Version

2.0

Created at

2022-09-08 03:46:44 UTC

Updated at

2022-09-08 03:46:44 UTC

NP-MRD ID

NP0261356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one

Description

Ajanoside belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. 2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one is found in Ajania fruticulosa. Based on a literature review very few articles have been published on Ajanoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082205462D          

 38 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082205462D          

 38 41  0  0  1  0            999 V2000
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 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  1  0  0  0
 18 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  6 34  1  0  0  0  0
  5 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1(OC=C(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)O1)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O13/c1-33-17-7-13(3-5-15(17)27)25(14-4-6-16(28)18(8-14)34-2)36-11-12(23(32)38-25)10-35-24-22(31)21(30)20(29)19(9-26)37-24/h3-8,11,19-22,24,26-31H,9-10H2,1-2H3/t19-,20-,21+,22-,24-/m1/s1

> <INCHI_KEY>
GQNKDXWCGZBLRB-WKKMNAASSA-N

> <FORMULA>
C25H28O13

> <MOLECULAR_WEIGHT>
536.486

> <EXACT_MASS>
536.152990962

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.889306005234545

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,4-dihydro-1,3-dioxin-4-one

> <JCHEM_LOGP>
0.6936664443333338

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.165052223853767

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.564946631214223

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835537473555

> <JCHEM_POLAR_SURFACE_AREA>
193.82999999999998

> <JCHEM_REFRACTIVITY>
126.32410000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.646  -6.209   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.688  -6.979   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.688  -8.519   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.021  -9.289   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.021 -10.829   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.355 -11.599   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.365 -12.779   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.892 -14.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.902 -15.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.385 -15.139   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.605 -16.318   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.141 -13.691   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.658 -13.424   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.185 -11.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.848 -12.512   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.882 -10.152   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.398  -9.885   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.388 -11.065   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.905 -10.797   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.431  -9.350   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.948  -9.083   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.475  -7.635   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.991  -7.368   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.518  -5.921   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.528  -4.741   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.981  -8.548   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.498  -8.280   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.455  -9.995   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.444 -11.175   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.938 -10.262   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.411 -11.709   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.861 -12.512   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.851 -13.691   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.345 -12.779   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.688 -11.599   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.646 -10.829   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.646  -9.289   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.980  -8.519   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7   16   34                                             
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    7                                                       
CONECT   16    6   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30                                                            
CONECT   32   18   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    6                                                       
CONECT   35    5   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₁₃

Average Mass

536.4860 Da

Monoisotopic Mass

536.15299 Da

IUPAC Name

2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,4-dihydro-1,3-dioxin-4-one

Traditional Name

2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1(OC=C(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)O1)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C25H28O13/c1-33-17-7-13(3-5-15(17)27)25(14-4-6-16(28)18(8-14)34-2)36-11-12(23(32)38-25)10-35-24-22(31)21(30)20(29)19(9-26)37-24/h3-8,11,19-22,24,26-31H,9-10H2,1-2H3/t19-,20-,21+,22-,24-/m1/s1

InChI Key

GQNKDXWCGZBLRB-WKKMNAASSA-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
Ajania fruticulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Ketal
Phenol
Monosaccharide
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Primary alcohol
Carbonyl group
Organooxygen compound
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	0.69	ChemAxon
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	193.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	126.32 m³·mol⁻¹	ChemAxon
Polarizability	51.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8567832

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10392390

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one (NP0261356)

MOL for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)

3D MOL for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)

3D SDF for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)

3D-SDF for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)

PDB for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)

3D PDB for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)

SMILES for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)

INCHI for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)

Structure for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)

3D Structure for NP0261356 (2,2-bis(4-hydroxy-3-methoxyphenyl)-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,3-dioxin-4-one)