NP-MRD: Showing NP-Card for Neoacrimarine C (NP0063211)

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Record Information

Version

2.0

Created at

2022-04-28 07:40:38 UTC

Updated at

2022-04-28 07:40:38 UTC

NP-MRD ID

NP0063211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neoacrimarine C

Description

7,11-Dihydroxy-6-{[(9S,10S)-9-hydroxy-8,8-dimethyl-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-10-yl]oxy}-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-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 C is found in Citrus hassaku and Citrus hybrid ''Yalaha''. Based on a literature review very few articles have been published on 7,11-dihydroxy-6-{[(9S,10S)-9-hydroxy-8,8-dimethyl-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-10-yl]oxy}-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209402D          

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M  END

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M  END


  Mrv1652304282209402D          

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    1.2546    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7378   -0.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8842    0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387   -0.3982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 12 15  1  0  0  0  0
 12 16  1  0  0  0  0
 10 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  9 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
  5 26  1  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
  4 29  1  0  0  0  0
 29 30  2  0  0  0  0
 28 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 27 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 33 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 31 41  1  0  0  0  0
 26 42  1  0  0  0  0
  1 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(O[C@@H]3[C@H](O)C(C)(C)OC4=CC=C5C=CC(=O)OC5=C34)C(O)=CC=C2C(=O)C2=C(O)C=C3OC(C)(C)C=CC3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C33H29NO9/c1-32(2)13-12-16-21(42-32)14-19(36)23-25(16)34(5)26-17(27(23)38)8-9-18(35)29(26)41-30-24-20(43-33(3,4)31(30)39)10-6-15-7-11-22(37)40-28(15)24/h6-14,30-31,35-36,39H,1-5H3/t30-,31-/m0/s1

> <INCHI_KEY>
NQAQWRPJTRYUKE-CONSDPRKSA-N

> <FORMULA>
C33H29NO9

> <MOLECULAR_WEIGHT>
583.593

> <EXACT_MASS>
583.184231518

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
59.764664863967155

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,11-dihydroxy-6-{[(13S,14S)-13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-14-yl]oxy}-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
5.240750899999999

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.10182036815182

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.301696546525093

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7488215175199118

> <JCHEM_POLAR_SURFACE_AREA>
134.99

> <JCHEM_REFRACTIVITY>
158.06389999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,11-dihydroxy-6-{[(13S,14S)-13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-14-yl]oxy}-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-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       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.383  -2.140   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.391  -3.304   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.887  -4.760   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.895  -5.924   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.407  -5.633   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.911  -4.178   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.903  -3.013   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.407  -1.558   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.383  -4.631   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.110  -3.211   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.391  -7.379   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.879  -7.670   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.870  -6.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.375  -5.051   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.366  -3.887   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.854  -4.178   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.846  -3.013   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.350  -5.633   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.358  -6.797   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       5.366   0.188   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.879   4.553   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.342   3.680   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.326   1.934   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.377  -0.488   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.650   0.932   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.358   5.427   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      10.899  -0.743   0.000  0.00  0.00           O+0
CONECT    1    2    6   43                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15   16                                             
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   12                                                            
CONECT   17   10   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19    9   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19                                                       
CONECT   26    5   27   42                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28    4   30                                                  
CONECT   30   29                                                            
CONECT   31   28   32   41                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   27   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39   40                                             
CONECT   38   37   33                                                       
CONECT   39   37                                                            
CONECT   40   37                                                            
CONECT   41   31                                                            
CONECT   42   26                                                            
CONECT   43    1                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₂₉NO₉

Average Mass

583.5930 Da

Monoisotopic Mass

583.18423 Da

IUPAC Name

7,11-dihydroxy-6-{[(13S,14S)-13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-14-yl]oxy}-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

Traditional Name

7,11-dihydroxy-6-{[(13S,14S)-13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-14-yl]oxy}-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one

CAS Registry Number

Not Available

SMILES

CN1C2=C(O[C@@H]3[C@H](O)C(C)(C)OC4=CC=C5C=CC(=O)OC5=C34)C(O)=CC=C2C(=O)C2=C(O)C=C3OC(C)(C)C=CC3=C12

InChI Identifier

InChI=1S/C33H29NO9/c1-32(2)13-12-16-21(42-32)14-19(36)23-25(16)34(5)26-17(27(23)38)8-9-18(35)29(26)41-30-24-20(43-33(3,4)31(30)39)10-6-15-7-11-22(37)40-28(15)24/h6-14,30-31,35-36,39H,1-5H3/t30-,31-/m0/s1

InChI Key

NQAQWRPJTRYUKE-CONSDPRKSA-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 hassaku	Plant	KNApSAcK
Citrus hybrid ''Yalaha''	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
Angular pyranocoumarin
Pyranochromene
Chromenopyridine
2,2-dimethyl-1-benzopyran
Coumarin
Dihydroquinolone
Dihydroquinoline
1-benzopyran
Benzopyran
Chromane
Pyranone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyran
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Secondary alcohol
Lactone
Azacycle
Ether
Oxacycle
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen 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
logP	4.59	ALOGPS
logP	5.24	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	134.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	158.06 m³·mol⁻¹	ChemAxon
Polarizability	59.76 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

163068824

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Neoacrimarine C (NP0063211)

MOL for NP0063211 (Neoacrimarine C)

3D MOL for NP0063211 (Neoacrimarine C)

3D SDF for NP0063211 (Neoacrimarine C)

3D-SDF for NP0063211 (Neoacrimarine C)

PDB for NP0063211 (Neoacrimarine C)

3D PDB for NP0063211 (Neoacrimarine C)

SMILES for NP0063211 (Neoacrimarine C)

INCHI for NP0063211 (Neoacrimarine C)

Structure for NP0063211 (Neoacrimarine C)

3D Structure for NP0063211 (Neoacrimarine C)