NP-MRD: Showing NP-Card for (-)-Acrimarine D (NP0083376)

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Record Information

Version

2.0

Created at

2022-04-29 04:26:46 UTC

Updated at

2022-04-29 04:26:46 UTC

NP-MRD ID

NP0083376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Acrimarine D

Description

Acrimarine D 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. (-)-Acrimarine D is found in Citrus aurantium and Citrus funadoka. Based on a literature review very few articles have been published on Acrimarine D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206262D          

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M  END

     RDKit          3D

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  Mrv1652304292206262D          

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 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  2  0  0  0  0
 10 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  9 37  1  0  0  0  0
 37 38  2  0  0  0  0
  4 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083376

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=O)C3=C(NC2=C1OC)C(C(C=C(C)C)C1=C(OC)C=C2OC(=O)C=CC2=C1)=C(OC)C=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C31H29NO8/c1-15(2)11-19(18-12-16-7-10-25(34)40-22(16)14-23(18)37-4)26-24(38-5)13-20(33)27-29(26)32-28-17(30(27)35)8-9-21(36-3)31(28)39-6/h7-14,19,33H,1-6H3,(H,32,35)

> <INCHI_KEY>
CSICEUBOWFUIAN-UHFFFAOYSA-N

> <FORMULA>
C31H29NO8

> <MOLECULAR_WEIGHT>
543.572

> <EXACT_MASS>
543.189316898

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
56.99581692111556

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxy-3,5,6-trimethoxy-4-[1-(7-methoxy-2-oxo-2H-chromen-6-yl)-3-methylbut-2-en-1-yl]-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
6.874532295999999

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.63883389102989

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.812614451734825

> <JCHEM_PKA_STRONGEST_BASIC>
-4.282230934443699

> <JCHEM_POLAR_SURFACE_AREA>
112.55000000000001

> <JCHEM_REFRACTIVITY>
151.2724

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-3,5,6-trimethoxy-4-[1-(7-methoxy-2-oxochromen-6-yl)-3-methylbut-2-en-1-yl]-10H-acridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -6.883  -4.034   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.550  -4.804   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.216  -4.034   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.882  -4.804   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.548  -4.034   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.215  -4.804   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.119  -4.034   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.119  -2.494   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.215  -6.344   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.119  -7.114   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.625  -6.794   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.656  -7.938   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.180  -9.403   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.210 -10.547   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.162  -7.618   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.638  -6.153   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.144  -5.833   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.607  -5.009   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.101  -5.329   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.071  -4.185   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.547  -2.720   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.516  -1.576   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.010  -1.896   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.021  -0.751   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.992  -0.111   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.962   1.034   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.437   2.498   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.498   0.209   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.529  -0.935   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.053  -2.400   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.083  -3.544   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.590  -3.224   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.643  -8.579   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.863  -8.899   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.894  -7.754   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.339 -10.363   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.548  -7.114   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.882  -6.344   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.216  -7.114   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.550  -6.344   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   38                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   37                                                  
CONECT   10    9   11   33                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   11   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   21   31                                                  
CONECT   31   30   18   32                                                  
CONECT   32   31                                                            
CONECT   33   10   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    9   38                                                       
CONECT   38   37    4   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39    2                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₂₉NO₈

Average Mass

543.5720 Da

Monoisotopic Mass

543.18932 Da

IUPAC Name

1-hydroxy-3,5,6-trimethoxy-4-[1-(7-methoxy-2-oxo-2H-chromen-6-yl)-3-methylbut-2-en-1-yl]-9,10-dihydroacridin-9-one

Traditional Name

1-hydroxy-3,5,6-trimethoxy-4-[1-(7-methoxy-2-oxochromen-6-yl)-3-methylbut-2-en-1-yl]-10H-acridin-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=O)C3=C(NC2=C1OC)C(C(C=C(C)C)C1=C(OC)C=C2OC(=O)C=CC2=C1)=C(OC)C=C3O

InChI Identifier

InChI=1S/C31H29NO8/c1-15(2)11-19(18-12-16-7-10-25(34)40-22(16)14-23(18)37-4)26-24(38-5)13-20(33)27-29(26)32-28-17(30(27)35)8-9-21(36-3)31(28)39-6/h7-14,19,33H,1-6H3,(H,32,35)

InChI Key

CSICEUBOWFUIAN-UHFFFAOYSA-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 funadoka	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
Coumarin
Dihydroquinolone
Benzopyran
Dihydroquinoline
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Lactone
Azacycle
Oxacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen 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	5.2	ALOGPS
logP	6.87	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	8.81	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	112.55 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	151.27 m³·mol⁻¹	ChemAxon
Polarizability	57 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052051

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

14886045

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Acrimarine D (NP0083376)

MOL for NP0083376 ((-)-Acrimarine D)

3D MOL for NP0083376 ((-)-Acrimarine D)

3D SDF for NP0083376 ((-)-Acrimarine D)

3D-SDF for NP0083376 ((-)-Acrimarine D)

PDB for NP0083376 ((-)-Acrimarine D)

3D PDB for NP0083376 ((-)-Acrimarine D)

SMILES for NP0083376 ((-)-Acrimarine D)

INCHI for NP0083376 ((-)-Acrimarine D)

Structure for NP0083376 ((-)-Acrimarine D)

3D Structure for NP0083376 ((-)-Acrimarine D)