NP-MRD: Showing NP-Card for (-)-Dalmaisione A (NP0080222)

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Record Information

Version

2.0

Created at

2022-04-29 01:16:35 UTC

Updated at

2022-04-29 01:16:36 UTC

NP-MRD ID

NP0080222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Dalmaisione A

Description

Dalmaisione A 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. (-)-Dalmaisione A is found in Polygala dalmaisiana and Polygala myrtifolia. Based on a literature review very few articles have been published on Dalmaisione A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203162D          

 42 47  0  0  1  0            999 V2000
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292203162D          

 42 47  0  0  1  0            999 V2000
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   -3.0662    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062    1.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5261   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860   -0.8348    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 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
 15 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  6  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  1  0  0  0
 33 36  1  1  0  0  0
 32 37  1  6  0  0  0
 31 38  1  1  0  0  0
 26 39  1  6  0  0  0
 25 40  1  1  0  0  0
 24 41  1  6  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=C3OC(=O)C4=C(OC5=CC=CC=C5C4=O)C3=CC=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O14/c1-10-17(30)20(33)22(35)27(37-10)42-25-21(34)19(32)15(9-29)40-28(25)39-14-8-4-6-12-23(14)41-26(36)16-18(31)11-5-2-3-7-13(11)38-24(12)16/h2-8,10,15,17,19-22,25,27-30,32-35H,9H2,1H3/t10-,15+,17-,19+,20+,21-,22+,25+,27-,28+/m0/s1

> <INCHI_KEY>
UHWGYDZWMICLSK-RPXMHYTLSA-N

> <FORMULA>
C28H28O14

> <MOLECULAR_WEIGHT>
588.518

> <EXACT_MASS>
588.147905582

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
56.889304259314635

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-11,12-dihydro-5,10-dioxatetraphene-11,12-dione

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
-1.093657551666667

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.719916022533258

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.100158944080388

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092580504791

> <JCHEM_POLAR_SURFACE_AREA>
210.89999999999998

> <JCHEM_REFRACTIVITY>
136.52909999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5,10-dioxatetraphene-11,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.366   0.188   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.879   4.553   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.358   5.427   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.342   3.680   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.195   2.807   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.699   1.352   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.211   1.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.219   2.225   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.715   3.680   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.203   3.971   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.699   5.427   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.707   6.591   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.219   6.300   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.228   7.464   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.723   8.919   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.211   9.210   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.203   8.046   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.691   8.337   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -3.707  10.665   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -6.732  10.083   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -7.740   7.173   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.723   4.844   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -6.732   1.934   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.715  -0.394   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -3.707  -1.558   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   41                                                  
CONECT   25   24   26   40                                                  
CONECT   26   25   27   39                                                  
CONECT   27   26   22   28                                                  
CONECT   28   27   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                                                            
CONECT   39   26                                                            
CONECT   40   25                                                            
CONECT   41   24   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₈O₁₄

Average Mass

588.5180 Da

Monoisotopic Mass

588.14791 Da

IUPAC Name

9-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-11,12-dihydro-5,10-dioxatetraphene-11,12-dione

Traditional Name

9-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5,10-dioxatetraphene-11,12-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=C3OC(=O)C4=C(OC5=CC=CC=C5C4=O)C3=CC=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C28H28O14/c1-10-17(30)20(33)22(35)27(37-10)42-25-21(34)19(32)15(9-29)40-28(25)39-14-8-4-6-12-23(14)41-26(36)16-18(31)11-5-2-3-7-13(11)38-24(12)16/h2-8,10,15,17,19-22,25,27-30,32-35H,9H2,1H3/t10-,15+,17-,19+,20+,21-,22+,25+,27-,28+/m0/s1

InChI Key

UHWGYDZWMICLSK-RPXMHYTLSA-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
Polygala dalmaisiana	Plant	KNApSAcK
Polygala myrtifolia	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
Chromone
Coumarin
Disaccharide
O-glycosyl compound
Benzopyran
1-benzopyran
Pyranone
Oxane
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organic oxide
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	0.62	ALOGPS
logP	-1.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	210.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	136.53 m³·mol⁻¹	ChemAxon
Polarizability	56.89 Å³	ChemAxon
Number of Rings	6	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

C00045274

Chemspider ID

9061696

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10886428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Dalmaisione A (NP0080222)

MOL for NP0080222 ((-)-Dalmaisione A)

3D MOL for NP0080222 ((-)-Dalmaisione A)

3D SDF for NP0080222 ((-)-Dalmaisione A)

3D-SDF for NP0080222 ((-)-Dalmaisione A)

PDB for NP0080222 ((-)-Dalmaisione A)

3D PDB for NP0080222 ((-)-Dalmaisione A)

SMILES for NP0080222 ((-)-Dalmaisione A)

INCHI for NP0080222 ((-)-Dalmaisione A)

Structure for NP0080222 ((-)-Dalmaisione A)

3D Structure for NP0080222 ((-)-Dalmaisione A)