NP-MRD: Showing NP-Card for (-)-Neoacrimarine E (NP0066619)

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Record Information

Version

2.0

Created at

2022-04-28 10:51:08 UTC

Updated at

2022-04-28 10:51:08 UTC

NP-MRD ID

NP0066619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Neoacrimarine E

Description

1-Hydroxy-4-[(4S)-5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-4-yl]-3,5,6-trimethoxy-9,10-dihydroacridin-9-one belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. (-)-Neoacrimarine E is found in Citrus aurantium, Citrus hybrids, Citrus paradisi , Citrus paradisii x Citrus tangerina and Citrus tangerina . Based on a literature review very few articles have been published on 1-hydroxy-4-[(4S)-5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-4-yl]-3,5,6-trimethoxy-9,10-dihydroacridin-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212512D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282212512D          

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    3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207    3.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334    3.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4862    1.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  2  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 21 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
 29 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 28 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 34 38  1  0  0  0  0
 38 39  1  0  0  0  0
 24 40  1  0  0  0  0
 22 41  1  0  0  0  0
 41 42  1  0  0  0  0
 18 43  1  0  0  0  0
 18 44  1  0  0  0  0
  8 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=O)C3=C(O)C=C(OC)C([C@@H]4CC(C)(C)OC5=C4C(O)=C4C=CC(=O)OC4=C5C(C)(C)C=C)=C3NC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C35H35NO9/c1-9-34(2,3)26-31-17(11-13-22(38)44-31)30(40)24-18(15-35(4,5)45-33(24)26)23-21(42-7)14-19(37)25-28(23)36-27-16(29(25)39)10-12-20(41-6)32(27)43-8/h9-14,18,37,40H,1,15H2,2-8H3,(H,36,39)/t18-/m0/s1

> <INCHI_KEY>
XFTQVQSYVLDGDM-SFHVURJKSA-N

> <FORMULA>
C35H35NO9

> <MOLECULAR_WEIGHT>
613.663

> <EXACT_MASS>
613.231181711

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
64.77002496592816

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxy-4-[(4S)-5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-4-yl]-3,5,6-trimethoxy-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
5.95

> <JCHEM_LOGP>
7.709645788666666

> <ALOGPS_LOGS>
-5.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.97645298446512

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.386093603046867

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2955763698693055

> <JCHEM_POLAR_SURFACE_AREA>
132.78

> <JCHEM_REFRACTIVITY>
169.2891

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-4-[(4S)-5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-8-oxo-3H,4H-pyrano[3,2-g]chromen-4-yl]-3,5,6-trimethoxy-10H-acridin-9-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      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.670   6.930   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.876   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.796   8.470   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.519   7.466   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.796   6.214   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      10.241   2.604   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   45                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13   14   16                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   12                                                            
CONECT   17   10   18                                                       
CONECT   18   17   19   43   44                                             
CONECT   19   18   20                                                       
CONECT   20   19    9   21                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   41                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   40                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   38                                                  
CONECT   35   34   28   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   34   39                                                       
CONECT   39   38                                                            
CONECT   40   24                                                            
CONECT   41   22   42                                                       
CONECT   42   41                                                            
CONECT   43   18                                                            
CONECT   44   18                                                            
CONECT   45    8                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₃₅NO₉

Average Mass

613.6630 Da

Monoisotopic Mass

613.23118 Da

IUPAC Name

1-hydroxy-4-[(4S)-5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-4-yl]-3,5,6-trimethoxy-9,10-dihydroacridin-9-one

Traditional Name

1-hydroxy-4-[(4S)-5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-8-oxo-3H,4H-pyrano[3,2-g]chromen-4-yl]-3,5,6-trimethoxy-10H-acridin-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=O)C3=C(O)C=C(OC)C([C@@H]4CC(C)(C)OC5=C4C(O)=C4C=CC(=O)OC4=C5C(C)(C)C=C)=C3NC2=C1OC

InChI Identifier

InChI=1S/C35H35NO9/c1-9-34(2,3)26-31-17(11-13-22(38)44-31)30(40)24-18(15-35(4,5)45-33(24)26)23-21(42-7)14-19(37)25-28(23)36-27-16(29(25)39)10-12-20(41-6)32(27)43-8/h9-14,18,37,40H,1,15H2,2-8H3,(H,36,39)/t18-/m0/s1

InChI Key

XFTQVQSYVLDGDM-SFHVURJKSA-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
Citrus aurantium	LOTUS Database	35616633
Citrus hybrids	Plant	KNApSAcK
Citrus paradisi	Plant	KNApSAcK
Citrus paradisii x Citrus tangerina	Plant	KNApSAcK
Citrus tangerina	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Pyranocoumarin
Linear pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Coumarin
Dihydroquinolone
Chromane
Benzopyran
Dihydroquinoline
1-benzopyran
Anisole
Pyranone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyridine
Pyran
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Lactone
Oxacycle
Azacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
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	5.95	ALOGPS
logP	7.71	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	7.39	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	132.78 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	169.29 m³·mol⁻¹	ChemAxon
Polarizability	64.77 Å³	ChemAxon
Number of Rings	6	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

163017887

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Neoacrimarine E (NP0066619)

MOL for NP0066619 ((-)-Neoacrimarine E)

3D MOL for NP0066619 ((-)-Neoacrimarine E)

3D SDF for NP0066619 ((-)-Neoacrimarine E)

3D-SDF for NP0066619 ((-)-Neoacrimarine E)

PDB for NP0066619 ((-)-Neoacrimarine E)

3D PDB for NP0066619 ((-)-Neoacrimarine E)

SMILES for NP0066619 ((-)-Neoacrimarine E)

INCHI for NP0066619 ((-)-Neoacrimarine E)

Structure for NP0066619 ((-)-Neoacrimarine E)

3D Structure for NP0066619 ((-)-Neoacrimarine E)