NP-MRD: Showing NP-Card for dalmaisione d (NP0182685)

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Record Information

Version

2.0

Created at

2022-09-03 21:27:03 UTC

Updated at

2022-09-03 21:27:03 UTC

NP-MRD ID

NP0182685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dalmaisione d

Description

Dalmaisione D belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). dalmaisione d is found in Polygala myrtifolia. dalmaisione d was first documented in 2008 (PMID: 18193886). Based on a literature review very few articles have been published on Dalmaisione D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223272D          

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M  END

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  5 10  1  0  0  0  0
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 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
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1O[C@@H](OCC2O[C@@H](OC3=CC=CC=C3\C=C3/OC4=CC=CC=C4C3=O)C(O)[C@@H](O)[C@@H]2O)C(O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O13/c28-10-17-20(30)22(32)24(34)26(39-17)36-11-18-21(31)23(33)25(35)27(40-18)38-14-7-3-1-5-12(14)9-16-19(29)13-6-2-4-8-15(13)37-16/h1-9,17-18,20-28,30-35H,10-11H2/b16-9-/t17?,18?,20-,21-,22+,23+,24?,25?,26-,27-/m1/s1

> <INCHI_KEY>
QKEXFCYHIQKPSV-TXXDBYDDSA-N

> <FORMULA>
C27H30O13

> <MOLECULAR_WEIGHT>
562.524

> <EXACT_MASS>
562.168641026

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.80551457866546

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-2-[(2-{[(2S,4S,5S)-3,4,5-trihydroxy-6-({[(2R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)methylidene]-2,3-dihydro-1-benzofuran-3-one

> <JCHEM_LOGP>
-1.1401947443333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.428116418385454

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.905284459374387

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
133.58490000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
dalmaisione D

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.400   1.365   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.630   2.698   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.090   2.698   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.320   1.365   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.220   1.365   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.990   2.698   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.220   4.032   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.990   5.366   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.220   6.699   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.990   8.033   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.220   9.367   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.320   9.367   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.090  10.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.630  10.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.400  12.034   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.320  12.034   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.090  13.368   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.220  12.034   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.990  13.368   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.990  10.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.530  10.700   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.530   5.366   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.300   6.699   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.300   4.032   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.840   4.032   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.530   2.698   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.300   1.365   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28   14   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   12   33                                                  
CONECT   33   32                                                            
CONECT   34    3   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35    2                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₁₃

Average Mass

562.5240 Da

Monoisotopic Mass

562.16864 Da

IUPAC Name

(2Z)-2-[(2-{[(2S,4S,5S)-3,4,5-trihydroxy-6-({[(2R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)methylidene]-2,3-dihydro-1-benzofuran-3-one

Traditional Name

dalmaisione D

CAS Registry Number

Not Available

SMILES

OCC1O[C@@H](OCC2O[C@@H](OC3=CC=CC=C3\C=C3/OC4=CC=CC=C4C3=O)C(O)[C@@H](O)[C@@H]2O)C(O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H30O13/c28-10-17-20(30)22(32)24(34)26(39-17)36-11-18-21(31)23(33)25(35)27(40-18)38-14-7-3-1-5-12(14)9-16-19(29)13-6-2-4-8-15(13)37-16/h1-9,17-18,20-28,30-35H,10-11H2/b16-9-/t17?,18?,20-,21-,22+,23+,24?,25?,26-,27-/m1/s1

InChI Key

QKEXFCYHIQKPSV-TXXDBYDDSA-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
Polygala myrtifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Phenolic glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzofuran
Coumaran
Phenoxy compound
Phenol ether
Aryl ketone
Benzenoid
Monocyclic benzene moiety
Oxane
Secondary alcohol
Ketone
Organoheterocyclic compound
Acetal
Polyol
Oxacycle
Organic oxide
Organic oxygen compound
Primary alcohol
Aldehyde
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Aurone flavonoids (LMPK12130022 )

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	-1.1	ChemAxon
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	133.58 m³·mol⁻¹	ChemAxon
Polarizability	55.81 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

C00014663

Chemspider ID

24846166

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607755

PDB ID

Not Available

ChEBI ID

187783

Good Scents ID

Not Available

References

General References

Harkat H, Blanc A, Weibel JM, Pale P: Versatile and expeditious synthesis of aurones via Au I-catalyzed cyclization. J Org Chem. 2008 Feb 15;73(4):1620-3. doi: 10.1021/jo702197b. Epub 2008 Jan 15. [PubMed:18193886 ]
LOTUS database [Link]

Showing NP-Card for dalmaisione d (NP0182685)

MOL for NP0182685 (dalmaisione d)

3D MOL for NP0182685 (dalmaisione d)

3D SDF for NP0182685 (dalmaisione d)

3D-SDF for NP0182685 (dalmaisione d)

PDB for NP0182685 (dalmaisione d)

3D PDB for NP0182685 (dalmaisione d)

SMILES for NP0182685 (dalmaisione d)

INCHI for NP0182685 (dalmaisione d)

Structure for NP0182685 (dalmaisione d)

3D Structure for NP0182685 (dalmaisione d)