NP-MRD: Showing NP-Card for (+)-Styraxjaponoside A (NP0072372)

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Record Information

Version

2.0

Created at

2022-04-28 17:43:25 UTC

Updated at

2022-04-28 17:43:25 UTC

NP-MRD ID

NP0072372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Styraxjaponoside A

Description

(3S,4R)-4-[(S)-(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]-3-[(S)-hydroxy(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. (+)-Styraxjaponoside A is found in Styrax japonica S.et Z. Based on a literature review very few articles have been published on (3S,4R)-4-[(S)-(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]-3-[(S)-hydroxy(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219432D          

 39 43  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652304282219432D          

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  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 14  1  1  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
  7 25  1  1  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 28  1  0  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  6  0  0  0
 33 36  1  1  0  0  0
 32 37  1  6  0  0  0
 31 38  1  1  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072372

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](O)[C@@H]1[C@H](COC1=O)[C@H](O)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O13/c1-34-16-6-12(3-5-15(16)38-26-24(32)23(31)22(30)18(8-27)39-26)21(29)19-13(9-35-25(19)33)20(28)11-2-4-14-17(7-11)37-10-36-14/h2-7,13,18-24,26-32H,8-10H2,1H3/t13-,18+,19-,20+,21+,22+,23-,24+,26+/m0/s1

> <INCHI_KEY>
NIIFAUHRYCGALG-HLXRISIQSA-N

> <FORMULA>
C26H30O13

> <MOLECULAR_WEIGHT>
550.513

> <EXACT_MASS>
550.168641026

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.082018935730794

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R)-4-[(S)-(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]-3-[(S)-hydroxy(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
-0.34

> <JCHEM_LOGP>
-1.1559734743333325

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.08353412068459

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.185472530918693

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
193.82999999999998

> <JCHEM_REFRACTIVITY>
127.87979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R)-4-[(S)-2H-1,3-benzodioxol-5-yl(hydroxy)methyl]-3-[(S)-hydroxy(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

> <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      12.270   9.919   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.735   9.444   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.055   7.937   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.911   6.907   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.446   7.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.126   8.889   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.302   6.352   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.837   6.828   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.345   6.828   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.821   8.293   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.361   8.293   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.266   9.539   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.925   3.613   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.622   4.846   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      15.520   7.461   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.840   5.955   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.880  10.474   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.344   9.998   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.664   8.492   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      18.129   8.016   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.273   9.046   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.953  10.553   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.489  11.029   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      17.168  12.535   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      20.098  11.583   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      20.738   8.570   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      18.449   6.510   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      19.914   6.034   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   28                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   25                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25    7                                                            
CONECT   26    3   27                                                       
CONECT   27   26                                                            
CONECT   28    2   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   29   35                                                  
CONECT   35   34                                                            
CONECT   36   33                                                            
CONECT   37   32                                                            
CONECT   38   31   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₁₃

Average Mass

550.5130 Da

Monoisotopic Mass

550.16864 Da

IUPAC Name

(3S,4R)-4-[(S)-(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]-3-[(S)-hydroxy(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

Traditional Name

(3S,4R)-4-[(S)-2H-1,3-benzodioxol-5-yl(hydroxy)methyl]-3-[(S)-hydroxy(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](O)[C@@H]1[C@H](COC1=O)[C@H](O)C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C26H30O13/c1-34-16-6-12(3-5-15(16)38-26-24(32)23(31)22(30)18(8-27)39-26)21(29)19-13(9-35-25(19)33)20(28)11-2-4-14-17(7-11)37-10-36-14/h2-7,13,18-24,26-32H,8-10H2,1H3/t13-,18+,19-,20+,21+,22+,23-,24+,26+/m0/s1

InChI Key

NIIFAUHRYCGALG-HLXRISIQSA-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
Styrax japonica S.et Z.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Dibenzylbutyrolactone
Lignan lactone
Tetrahydrofuran lignan
9,9p-epoxylignan
Furanoid lignan
Fatty acyl glycoside
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Benzodioxole
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Alkyl aryl ether
Benzenoid
Fatty acyl
Oxane
Monocyclic benzene moiety
Monosaccharide
Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Ether
Acetal
Carbonyl group
Primary alcohol
Aromatic alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.34	ALOGPS
logP	-1.2	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.19	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	127.88 m³·mol⁻¹	ChemAxon
Polarizability	53.08 Å³	ChemAxon
Number of Rings	5	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

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

163050462

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Styraxjaponoside A (NP0072372)

MOL for NP0072372 ((+)-Styraxjaponoside A)

3D MOL for NP0072372 ((+)-Styraxjaponoside A)

3D SDF for NP0072372 ((+)-Styraxjaponoside A)

3D-SDF for NP0072372 ((+)-Styraxjaponoside A)

PDB for NP0072372 ((+)-Styraxjaponoside A)

3D PDB for NP0072372 ((+)-Styraxjaponoside A)

SMILES for NP0072372 ((+)-Styraxjaponoside A)

INCHI for NP0072372 ((+)-Styraxjaponoside A)

Structure for NP0072372 ((+)-Styraxjaponoside A)

3D Structure for NP0072372 ((+)-Styraxjaponoside A)