NP-MRD: Showing NP-Card for Dalpanin (NP0054108)

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Record Information

Version

2.0

Created at

2022-04-28 00:34:06 UTC

Updated at

2022-04-28 00:34:06 UTC

NP-MRD ID

NP0054108

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dalpanin

Description

(3S)-5,7-dihydroxy-3-[(2S)-6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-4-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. Dalpanin is found in Dalbergia paniculata . Based on a literature review very few articles have been published on (3S)-5,7-dihydroxy-3-[(2S)-6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202342D          

 38 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282202342D          

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 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  6  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 24 36  1  0  0  0  0
  3 37  1  0  0  0  0
  1 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054108

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H]1CC2=CC([C@H]3COC4=C([C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(O)=CC(O)=C4C3=O)=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O12/c1-26(2,35)17-4-9-3-10(12(28)6-15(9)37-17)11-8-36-24-18(20(11)31)13(29)5-14(30)19(24)25-23(34)22(33)21(32)16(7-27)38-25/h3,5-6,11,16-17,21-23,25,27-30,32-35H,4,7-8H2,1-2H3/t11-,16-,17+,21-,22+,23-,25+/m1/s1

> <INCHI_KEY>
FBAPMDCZDDOJRF-IKCRZDEGSA-N

> <FORMULA>
C26H30O12

> <MOLECULAR_WEIGHT>
534.514

> <EXACT_MASS>
534.173726406

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.51040963650652

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5,7-dihydroxy-3-[(2S)-6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
0.14

> <JCHEM_LOGP>
-0.08062879933333386

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.118280591464444

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.441311757664866

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1063772201343935

> <JCHEM_POLAR_SURFACE_AREA>
206.6

> <JCHEM_REFRACTIVITY>
129.5871

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5,7-dihydroxy-3-[(2S)-6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydro-1-benzopyran-4-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      16.790   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.456   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.123   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.123   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.456   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.790   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.124   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.457   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.791   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.791   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.457   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.124   4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.457   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      20.791   1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      22.125   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      22.125   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      19.457   8.470   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      15.456   4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.123   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.789   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.789   6.160   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.455   6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.323   4.326   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.418   3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.323   1.834   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.878   3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.338   3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.878   4.620   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.878   1.540   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      12.789   1.540   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      12.789   9.240   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      18.124   9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16    9                                                            
CONECT   17    8                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20    4   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24   28                                                  
CONECT   24   23   25   36                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   24                                                            
CONECT   37    3                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₁₂

Average Mass

534.5140 Da

Monoisotopic Mass

534.17373 Da

IUPAC Name

(3S)-5,7-dihydroxy-3-[(2S)-6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(3S)-5,7-dihydroxy-3-[(2S)-6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1CC2=CC([C@H]3COC4=C([C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(O)=CC(O)=C4C3=O)=C(O)C=C2O1

InChI Identifier

InChI=1S/C26H30O12/c1-26(2,35)17-4-9-3-10(12(28)6-15(9)37-17)11-8-36-24-18(20(11)31)13(29)5-14(30)19(24)25-23(34)22(33)21(32)16(7-27)38-25/h3,5-6,11,16-17,21-23,25,27-30,32-35H,4,7-8H2,1-2H3/t11-,16-,17+,21-,22+,23-,25+/m1/s1

InChI Key

FBAPMDCZDDOJRF-IKCRZDEGSA-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
Dalbergia paniculata	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
3'-prenylated isoflavanone
Isoflavonoid-8-c-glycoside
Isoflavonoid c-glycoside
Hydroxyisoflavonoid
Isoflavanone
Isoflavanol
Isoflavonoid
Isoflavonoid skeleton
Isoflavan
Phenolic glycoside
Glycosyl compound
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
Chromane
Coumaran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	0.14	ALOGPS
logP	-0.081	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.44	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	129.59 m³·mol⁻¹	ChemAxon
Polarizability	53.51 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	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

162822813

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Dalpanin (NP0054108)

MOL for NP0054108 (Dalpanin)

3D MOL for NP0054108 (Dalpanin)

3D SDF for NP0054108 (Dalpanin)

3D-SDF for NP0054108 (Dalpanin)

PDB for NP0054108 (Dalpanin)

3D PDB for NP0054108 (Dalpanin)

SMILES for NP0054108 (Dalpanin)

INCHI for NP0054108 (Dalpanin)

Structure for NP0054108 (Dalpanin)

3D Structure for NP0054108 (Dalpanin)