NP-MRD: Showing NP-Card for Macrostachyol A (NP0332865)

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Record Information

Version

2.0

Created at

2024-05-01 15:47:16 UTC

Updated at

2025-05-24 00:05:37 UTC

NP-MRD ID

NP0332865

Natural Product DOI

https://doi.org/10.57994/2143

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Macrostachyol A

Description

Macrostachyol A belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Based on a literature review very few articles have been published on Macrostachyol A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01132318242D          

 69 79  0  0  1  0            999 V2000
    3.4904   -0.7832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759   -1.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 67  1  0  0  0  0
  5 68  1  0  0  0  0
 68 69  2  0  0  0  0
  2 69  1  0  0  0  0
M  END


  Mrv2104 01132318242D          

 69 79  0  0  1  0            999 V2000
    3.4904   -0.7832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759   -1.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 18 55  1  0  0  0  0
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 55 56  2  0  0  0  0
 14 56  1  0  0  0  0
 13 57  1  0  0  0  0
 57 58  1  1  0  0  0
 58 59  2  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 61 63  1  0  0  0  0
 63 64  2  0  0  0  0
 58 64  1  0  0  0  0
 57 65  1  0  0  0  0
 12 66  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  2  0  0  0  0
  8 67  1  0  0  0  0
  5 68  1  0  0  0  0
 68 69  2  0  0  0  0
  2 69  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C\C2=CC(O)=C3[C@@H]([C@H](OC3=C2)C2=CC=C(O)C=C2)C2=CC(O)=C3[C@@H]([C@H](OC3=C2)C2=CC=C(O)C=C2)C2=CC(O)=C3[C@@H]([C@H](OC3=C2)C2=CC=C(O)C=C2O)C2=CC(O)=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C56H42O13/c57-34-9-3-27(4-10-34)1-2-28-17-42(64)51-45(18-28)67-54(29-5-11-35(58)12-6-29)48(51)32-21-43(65)52-46(23-32)68-55(30-7-13-36(59)14-8-30)49(52)33-22-44(66)53-47(24-33)69-56(40-16-15-37(60)26-41(40)63)50(53)31-19-38(61)25-39(62)20-31/h1-26,48-50,54-66H/b2-1+/t48-,49-,50-,54+,55+,56+/m0/s1

> <INCHI_KEY>
PEVBAYOVLPTDQL-UXGYSEAKSA-N

> <FORMULA>
C56H42O13

> <MOLECULAR_WEIGHT>
922.939

> <EXACT_MASS>
922.262541412

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
99.6708640527246

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(2S,3S)-2-(2,4-dihydroxyphenyl)-4-hydroxy-6-[(2S,3S)-4-hydroxy-6-[(2S,3S)-4-hydroxy-2-(4-hydroxyphenyl)-6-[(1E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

> <JCHEM_LOGP>
10.773136315666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.866200692608633

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.461670509211903

> <JCHEM_PKA_STRONGEST_BASIC>
-5.511048288859304

> <JCHEM_POLAR_SURFACE_AREA>
229.98999999999995

> <JCHEM_REFRACTIVITY>
257.1883999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2S,3S)-2-(2,4-dihydroxyphenyl)-4-hydroxy-6-[(2S,3S)-4-hydroxy-6-[(2S,3S)-4-hydroxy-2-(4-hydroxyphenyl)-6-[(1E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JAN-23         0                                  
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HETATM    2  C   UNK     0       5.182  -2.232   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.182  -3.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.848  -4.542   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.514  -3.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.181  -4.542   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.181  -6.082   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.153  -6.852   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.153  -8.392   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.487  -9.162   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.487 -10.702   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.820  -8.392   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.285  -8.868   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.761 -10.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.730 -11.477   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.206 -12.942   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.176 -14.086   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.713 -13.262   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.483 -14.595   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.856 -16.002   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.325 -16.163   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.698 -17.570   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.167 -17.731   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.604 -18.816   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.283 -20.322   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.876 -20.949   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.631 -20.044   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.224 -20.670   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.022 -19.765   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.063 -22.202   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.309 -23.107   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.148 -24.638   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.715 -22.480   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.617 -21.092   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.778 -22.624   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.532 -23.529   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.693 -25.061   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.100 -25.687   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.261 -27.219   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -7.346 -24.782   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -7.185 -23.250   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -8.431 -22.345   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -6.761 -20.062   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -6.135 -18.655   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -6.761 -17.248   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -7.989 -14.275   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -9.133 -15.306   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -8.813 -16.812   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -9.958 -17.843   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -11.422 -17.367   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0     -12.567 -18.397   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0     -11.742 -15.860   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -10.598 -14.830   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -8.150 -12.744   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -6.743 -12.117   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -6.267 -10.653   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -5.190  -7.622   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -6.730  -7.622   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -7.500  -8.956   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -9.040  -8.956   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -9.810  -7.622   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0     -11.350  -7.622   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      -9.040  -6.288   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -7.500  -6.288   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      -4.285  -6.376   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      -2.820  -6.852   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      -1.487  -6.082   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       2.514  -2.232   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       3.848  -1.462   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   69                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   68                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   67                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   66                                                  
CONECT   13   12   14   57                                                  
CONECT   14   13   15   56                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   55                                                  
CONECT   19   18   20   46                                                  
CONECT   20   19   21   45                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   44                                                  
CONECT   25   24   26   34                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26                                                       
CONECT   34   25   35   43                                                  
CONECT   35   34   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   35   42                                                  
CONECT   42   41                                                            
CONECT   43   34   44                                                       
CONECT   44   24   43   45                                                  
CONECT   45   44   20                                                       
CONECT   46   19   47   54                                                  
CONECT   47   46   48   53                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   47                                                       
CONECT   54   46   55                                                       
CONECT   55   18   54   56                                                  
CONECT   56   55   14                                                       
CONECT   57   13   58   65                                                  
CONECT   58   57   59   64                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   64                                                       
CONECT   64   63   58                                                       
CONECT   65   57   66                                                       
CONECT   66   12   65   67                                                  
CONECT   67   66    8                                                       
CONECT   68    5   69                                                       
CONECT   69   68    2                                                       
MASTER        0    0    0    0    0    0    0    0   69    0  158    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₆H₄₂O₁₃

Average Mass

922.9390 Da

Monoisotopic Mass

922.26254 Da

IUPAC Name

5-[(2S,3S)-2-(2,4-dihydroxyphenyl)-4-hydroxy-6-[(2S,3S)-4-hydroxy-6-[(2S,3S)-4-hydroxy-2-(4-hydroxyphenyl)-6-[(1E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C\C2=CC(O)=C3[C@@H]([C@H](OC3=C2)C2=CC=C(O)C=C2)C2=CC(O)=C3[C@@H]([C@H](OC3=C2)C2=CC=C(O)C=C2)C2=CC(O)=C3[C@@H]([C@H](OC3=C2)C2=CC=C(O)C=C2O)C2=CC(O)=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C56H42O13/c57-34-9-3-27(4-10-34)1-2-28-17-42(64)51-45(18-28)67-54(29-5-11-35(58)12-6-29)48(51)32-21-43(65)52-46(23-32)68-55(30-7-13-36(59)14-8-30)49(52)33-22-44(66)53-47(24-33)69-56(40-16-15-37(60)26-41(40)63)50(53)31-19-38(61)25-39(62)20-31/h1-26,48-50,54-66H/b2-1+/t48-,49-,50-,54+,55+,56+/m0/s1

InChI Key

PEVBAYOVLPTDQL-UXGYSEAKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	[email protected]	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.17 MHz, C2D6OS, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, C2D6OS, simulated)	[email protected]	University of Geneva	Olivier Kirchhoffer	2025-05-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.17, C2D6OS, simulated)	[email protected]	University of Geneva	Olivier Kirchhoffer	2024-05-01	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Gnetum edule		Not Available
Gnetum edule		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Diterpenoid
Linear 1,7-diphenylheptane skeleton
1-phenylcoumaran
Stilbene
Coumaran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	10.77	ChemAxon
pKa (Strongest Acidic)	8.46	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	229.99 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	257.19 m³·mol⁻¹	ChemAxon
Polarizability	99.67 Å³	ChemAxon
Number of Rings	11	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Macrostachyol A (NP0332865)

MOL for NP0332865 (Macrostachyol A)

3D MOL for NP0332865 (Macrostachyol A)

3D SDF for NP0332865 (Macrostachyol A)

3D-SDF for NP0332865 (Macrostachyol A)

PDB for NP0332865 (Macrostachyol A)

3D PDB for NP0332865 (Macrostachyol A)

SMILES for NP0332865 (Macrostachyol A)

INCHI for NP0332865 (Macrostachyol A)

Structure for NP0332865 (Macrostachyol A)

3D Structure for NP0332865 (Macrostachyol A)