NP-MRD: Showing NP-Card for (5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one (NP0279910)

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Record Information

Version

2.0

Created at

2022-09-09 05:28:03 UTC

Updated at

2022-09-09 05:28:03 UTC

NP-MRD ID

NP0279910

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one

Description

Alopecurone C belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one is found in Sophora alopecuroides. Based on a literature review a small amount of articles have been published on Alopecurone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092207282D          

 42 47  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092207282D          

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   -0.5609    0.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 14 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  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
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
 34 42  1  0  0  0  0
  7 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0279910

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2O[C@@H](CC(=O)C2=C(O)C2=C1O[C@@H]([C@H]2C1=CC(O)=CC(O)=C1)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H30O8/c1-17(2)3-12-25-33-29(26(39)16-27(41-33)18-4-8-21(35)9-5-18)31(40)30-28(20-13-23(37)15-24(38)14-20)32(42-34(25)30)19-6-10-22(36)11-7-19/h3-11,13-15,27-28,32,35-38,40H,12,16H2,1-2H3/t27-,28-,32+/m0/s1

> <INCHI_KEY>
OEYSIPNWFNKKRF-ALKXEMMNSA-N

> <FORMULA>
C34H30O8

> <MOLECULAR_WEIGHT>
566.606

> <EXACT_MASS>
566.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
61.2710949790924

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6S,12S)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1,3(7),8-trien-10-one

> <JCHEM_LOGP>
7.121778633333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.0511941312359

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.557224988634436

> <JCHEM_PKA_STRONGEST_BASIC>
-4.644925395244663

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
158.11659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S,12S)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0^{3,7}]trideca-1,3(7),8-trien-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.471  -9.773   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.137  -9.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.197  -9.773   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.137  -7.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -6.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.197  -0.533   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.602  -4.859   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.047  -3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.817  -4.947   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.357  -4.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.127  -3.613   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.667  -3.613   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.357  -2.279   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.817  -2.279   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.602  -2.367   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.077  -0.902   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.584  -0.582   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.060   0.882   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.566   1.203   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.029   2.027   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.523   1.707   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.492   2.851   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.047   0.242   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.864  -0.533   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.531  -5.153   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.199  -5.153   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.199  -6.693   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.533  -7.463   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       7.865  -7.463   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.531  -6.693   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.864  -5.153   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   42                                                  
CONECT    8    7    9   31                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   22                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22   14   11   23                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23                                                       
CONECT   31    8   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   42                                                  
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                                                       
CONECT   42   34    7                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₀O₈

Average Mass

566.6060 Da

Monoisotopic Mass

566.19407 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2O[C@@H](CC(=O)C2=C(O)C2=C1O[C@@H]([C@H]2C1=CC(O)=CC(O)=C1)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C34H30O8/c1-17(2)3-12-25-33-29(26(39)16-27(41-33)18-4-8-21(35)9-5-18)31(40)30-28(20-13-23(37)15-24(38)14-20)32(42-34(25)30)19-6-10-22(36)11-7-19/h3-11,13-15,27-28,32,35-38,40H,12,16H2,1-2H3/t27-,28-,32+/m0/s1

InChI Key

OEYSIPNWFNKKRF-ALKXEMMNSA-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
Sophora alopecuroides	LOTUS Database	35616633

Chemical Taxonomy

Description

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
8-prenylated flavanone
7-prenylated 2-arybenzofuran
8-prenylated flavan
Linear 1,7-diphenylheptane skeleton
Furanoflavonoid or dihydroflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Neolignan skeleton
Flavanone
Hydroxyflavonoid
Flavan
1-phenylcoumaran
Stilbene
Furanochromone
Chromone
Benzopyran
1-benzopyran
Chromane
Coumaran
Benzofuran
Aryl alkyl ketone
Aryl ketone
Resorcinol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00014267

Chemspider ID

59002703

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101915835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one (NP0279910)

MOL for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)

3D MOL for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)

3D SDF for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)

3D-SDF for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)

PDB for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)

3D PDB for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)

SMILES for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)

INCHI for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)

Structure for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)

3D Structure for NP0279910 ((5s,6s,12s)-6-(3,5-dihydroxyphenyl)-8-hydroxy-5,12-bis(4-hydroxyphenyl)-2-(3-methylbut-2-en-1-yl)-4,13-dioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-10-one)