NP-MRD: Showing NP-Card for Brackenin (NP0054397)

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Record Information

Version

2.0

Created at

2022-04-28 00:45:38 UTC

Updated at

2022-04-28 00:45:38 UTC

NP-MRD ID

NP0054397

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brackenin

Description

(2R,3S)-1,4-bis(2,4-dihydroxyphenyl)-2,3-bis[(4-hydroxyphenyl)methyl]butane-1,4-dione belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. Brackenin is found in Brackenridgea zanguebarica . Based on a literature review very few articles have been published on (2R,3S)-1,4-bis(2,4-dihydroxyphenyl)-2,3-bis[(4-hydroxyphenyl)methyl]butane-1,4-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202452D          

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M  END

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M  END


  Mrv1652304282202452D          

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M  END
> <DATABASE_ID>
NP0054397

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C[C@H]([C@H](CC2=CC=C(O)C=C2)C(=O)C2=C(O)C=C(O)C=C2)C(=O)C2=CC=C(O)C=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O8/c31-19-5-1-17(2-6-19)13-25(29(37)23-11-9-21(33)15-27(23)35)26(14-18-3-7-20(32)8-4-18)30(38)24-12-10-22(34)16-28(24)36/h1-12,15-16,25-26,31-36H,13-14H2/t25-,26+

> <INCHI_KEY>
BSKPRHTXUTXRJW-WMPKNSHKSA-N

> <FORMULA>
C30H26O8

> <MOLECULAR_WEIGHT>
514.53

> <EXACT_MASS>
514.162767797

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.817709622278194

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-1,4-bis(2,4-dihydroxyphenyl)-2,3-bis[(4-hydroxyphenyl)methyl]butane-1,4-dione

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
6.831321032666667

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.117255335827004

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.541727650362456

> <JCHEM_PKA_STRONGEST_BASIC>
-4.910530774292789

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
141.59760000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.13e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-1,4-bis(2,4-dihydroxyphenyl)-2,3-bis[(4-hydroxyphenyl)methyl]butane-1,4-dione

> <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       5.642   1.244   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.308   0.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.308  -1.066   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.642  -1.836   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.976  -1.066   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.976   0.474   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.642  -3.376   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.498  -2.345   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.976  -4.146   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.383  -4.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.628  -3.867   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.035  -4.493   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.468  -2.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.061  -1.709   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.900  -0.177   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.146   0.728   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.552   0.101   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.713  -1.430   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.120  -2.056   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.985   2.259   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.544  -6.304   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.950  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.196  -6.025   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.603  -6.651   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.764  -8.183   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.518  -9.088   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.111  -8.462   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.171  -8.809   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.730  -5.051   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.323  -4.425   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.077  -5.330   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.670  -4.703   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.509  -3.172   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.755  -2.267   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.162  -2.893   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.102  -2.545   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.802  -1.386   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.642   2.784   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    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   29                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   16                                                            
CONECT   21   10   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25                                                            
CONECT   29    9   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   33                                                            
CONECT   37    3                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₈

Average Mass

514.5300 Da

Monoisotopic Mass

514.16277 Da

IUPAC Name

(2R,3S)-1,4-bis(2,4-dihydroxyphenyl)-2,3-bis[(4-hydroxyphenyl)methyl]butane-1,4-dione

Traditional Name

(2R,3S)-1,4-bis(2,4-dihydroxyphenyl)-2,3-bis[(4-hydroxyphenyl)methyl]butane-1,4-dione

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C[C@H]([C@H](CC2=CC=C(O)C=C2)C(=O)C2=C(O)C=C(O)C=C2)C(=O)C2=CC=C(O)C=C2O)C=C1

InChI Identifier

InChI=1S/C30H26O8/c31-19-5-1-17(2-6-19)13-25(29(37)23-11-9-21(33)15-27(23)35)26(14-18-3-7-20(32)8-4-18)30(38)24-12-10-22(34)16-28(24)36/h1-12,15-16,25-26,31-36H,13-14H2/t25-,26+

InChI Key

BSKPRHTXUTXRJW-WMPKNSHKSA-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
Brackenridgea zanguebarica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane lignans

Alternative Parents

Substituents

Dibenzylbutane lignan skeleton
2'-hydroxy-dihydrochalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Alkyl-phenylketone
Butyrophenone
Phenylketone
Aryl alkyl ketone
Aryl ketone
Benzoyl
Resorcinol
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.28	ALOGPS
logP	6.83	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.54	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	141.6 m³·mol⁻¹	ChemAxon
Polarizability	51.82 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

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

163089640

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Brackenin (NP0054397)

MOL for NP0054397 (Brackenin)

3D MOL for NP0054397 (Brackenin)

3D SDF for NP0054397 (Brackenin)

3D-SDF for NP0054397 (Brackenin)

PDB for NP0054397 (Brackenin)

3D PDB for NP0054397 (Brackenin)

SMILES for NP0054397 (Brackenin)

INCHI for NP0054397 (Brackenin)

Structure for NP0054397 (Brackenin)

3D Structure for NP0054397 (Brackenin)