NP-MRD: Showing NP-Card for (2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one (NP0266012)

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Record Information

Version

2.0

Created at

2022-09-08 10:12:27 UTC

Updated at

2022-09-08 10:12:27 UTC

NP-MRD ID

NP0266012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one

Description

(2R)-9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-2,3,5,10-tetrahydro-1,4-dioxa-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. (2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one is found in Citrus paradisi. Based on a literature review very few articles have been published on (2R)-9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-2,3,5,10-tetrahydro-1,4-dioxa-5-azatetraphen-10-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082212122D          

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 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 26 37  2  0  0  0  0
 31 37  1  0  0  0  0
 22 38  1  0  0  0  0
 13 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266012

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=CC=C4O[C@@](C)(COC4=C3N(C)C2=C1)\C=C\C1=C2OC(=O)C=CC2=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H23NO8/c1-29(11-10-17-20(31)7-4-15-5-9-23(33)37-27(15)17)14-36-28-22(38-29)8-6-18-25(28)30(2)19-12-16(35-3)13-21(32)24(19)26(18)34/h4-13,31-32H,14H2,1-3H3/b11-10+/t29-/m1/s1

> <INCHI_KEY>
AEXHLHGCDOTWGS-WBKPCLEFSA-N

> <FORMULA>
C29H23NO8

> <MOLECULAR_WEIGHT>
513.502

> <EXACT_MASS>
513.142366705

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
53.5911897520216

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-2,3,5,10-tetrahydro-1,4-dioxa-5-azatetraphen-10-one

> <JCHEM_LOGP>
5.0061318230000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.872429024771982

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.762591145367277

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4497291804372265

> <JCHEM_POLAR_SURFACE_AREA>
114.76000000000002

> <JCHEM_REFRACTIVITY>
140.07100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3H-1,4-dioxa-5-azatetraphen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.769 -17.519   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.780 -16.339   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.306 -14.892   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.823 -14.625   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.350 -13.178   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.866 -12.910   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.360 -11.998   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.886 -10.551   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.403 -10.283   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.896  -9.371   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.423  -7.924   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.433  -6.744   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.917  -7.012   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.390  -8.459   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.380  -9.639   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       8.853 -11.086   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       7.337 -11.353   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.843 -12.265   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.316 -13.712   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.873  -8.726   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.883  -7.547   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.410  -6.099   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.894  -5.832   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.410  -4.559   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.744  -3.789   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.744  -2.249   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.410  -1.479   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.077  -2.249   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.410   0.061   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.744   0.831   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.078   0.061   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.411   0.831   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.745   0.061   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.745  -1.479   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.079  -2.249   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      10.411  -2.249   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.078  -1.479   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.927  -5.832   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   38                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    7   19                                                  
CONECT   19   18    3                                                       
CONECT   20   14   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   38                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   37                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   26   31                                                  
CONECT   38   22   13                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₃NO₈

Average Mass

513.5020 Da

Monoisotopic Mass

513.14237 Da

IUPAC Name

(2R)-9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-2,3,5,10-tetrahydro-1,4-dioxa-5-azatetraphen-10-one

Traditional Name

(2R)-9-hydroxy-2-[(E)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3H-1,4-dioxa-5-azatetraphen-10-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=CC=C4O[C@@](C)(COC4=C3N(C)C2=C1)\C=C\C1=C2OC(=O)C=CC2=CC=C1O

InChI Identifier

InChI=1S/C29H23NO8/c1-29(11-10-17-20(31)7-4-15-5-9-23(33)37-27(15)17)14-36-28-22(38-29)8-6-18-25(28)30(2)19-12-16(35-3)13-21(32)24(19)26(18)34/h4-13,31-32H,14H2,1-3H3/b11-10+/t29-/m1/s1

InChI Key

AEXHLHGCDOTWGS-WBKPCLEFSA-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
Citrus paradisi	LOTUS Database	35616633

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
7-hydroxycoumarin
Hydroxycoumarin
Coumarin
Dihydroquinolone
Benzo-1,4-dioxane
Benzodioxane
Benzopyran
Dihydroquinoline
1-benzopyran
Anisole
Styrene
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Para-dioxin
Pyridine
Vinylogous acid
Vinylogous amide
Heteroaromatic compound
Lactone
Azacycle
Ether
Oxacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	5.01	ChemAxon
pKa (Strongest Acidic)	7.76	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	140.07 m³·mol⁻¹	ChemAxon
Polarizability	53.59 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	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

163188888

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one (NP0266012)

MOL for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)

3D MOL for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)

3D SDF for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)

3D-SDF for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)

PDB for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)

3D PDB for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)

SMILES for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)

INCHI for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)

Structure for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)

3D Structure for NP0266012 ((2r)-9-hydroxy-2-[(1e)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-7-methoxy-2,5-dimethyl-3h-1,4-dioxa-5-azatetraphen-10-one)