NP-MRD: Showing NP-Card for 1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one (NP0222161)

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Record Information

Version

2.0

Created at

2022-09-05 23:55:24 UTC

Updated at

2022-09-05 23:55:24 UTC

NP-MRD ID

NP0222161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one

Description

1-Hydroxy-4-[(8R,9R)-8-(2-hydroxypropan-2-yl)-2-oxo-2H,8H,9H-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methyl-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. 1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one is found in Citrus paradisi. Based on a literature review very few articles have been published on 1-hydroxy-4-[(8R,9R)-8-(2-hydroxypropan-2-yl)-2-oxo-2H,8H,9H-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methyl-9,10-dihydroacridin-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062201552D          

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M  END

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  Mrv1652309062201552D          

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    3.2943   -4.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3174   -3.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  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  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 18 28  2  0  0  0  0
 22 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 16 35  2  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
  6 38  1  0  0  0  0
 38 39  2  0  0  0  0
  3 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=O)C3=C(O)C=C(OC)C([C@H]4[C@@H](OC5=CC=C6C=CC(=O)OC6=C45)C(C)(C)O)=C3N(C)C2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C31H29NO9/c1-31(2,36)30-24(23-17(40-30)10-7-14-8-12-20(34)41-28(14)23)22-19(38-5)13-16(33)21-26(22)32(3)25-15(27(21)35)9-11-18(37-4)29(25)39-6/h7-13,24,30,33,36H,1-6H3/t24-,30-/m1/s1

> <INCHI_KEY>
XRRKNHPPSZSNHE-AYWVHJORSA-N

> <FORMULA>
C31H29NO9

> <MOLECULAR_WEIGHT>
559.571

> <EXACT_MASS>
559.184231518

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.37983867667828

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxy-4-[(8R,9R)-8-(2-hydroxypropan-2-yl)-2-oxo-2H,8H,9H-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methyl-9,10-dihydroacridin-9-one

> <JCHEM_LOGP>
4.254300349666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.27592279286075

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.846219496740156

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1155120942478307

> <JCHEM_POLAR_SURFACE_AREA>
123.99000000000002

> <JCHEM_REFRACTIVITY>
150.17839999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-4-[(8R,9R)-8-(2-hydroxypropan-2-yl)-2-oxo-8H,9H-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.582  -7.835   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.106  -9.300   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.136 -10.444   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.643 -10.124   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.118  -8.659   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.625  -8.339   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.101  -6.875   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.070  -5.730   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.546  -4.266   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      12.564  -6.050   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.088  -7.515   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.566  -9.300   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.090  -7.835   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.625  -7.359   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.161  -6.883   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.101  -5.895   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.149  -8.824   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       6.193  -6.855   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   38                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   35                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   35                                                  
CONECT   17   16   18   30                                                  
CONECT   18   17   19   28                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   18   22                                                  
CONECT   29   19   30                                                       
CONECT   30   29   17   31                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   16    9   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    6   39                                                  
CONECT   39   38    3   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₂₉NO₉

Average Mass

559.5710 Da

Monoisotopic Mass

559.18423 Da

IUPAC Name

1-hydroxy-4-[(8R,9R)-8-(2-hydroxypropan-2-yl)-2-oxo-2H,8H,9H-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1-hydroxy-4-[(8R,9R)-8-(2-hydroxypropan-2-yl)-2-oxo-8H,9H-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=O)C3=C(O)C=C(OC)C([C@H]4[C@@H](OC5=CC=C6C=CC(=O)OC6=C45)C(C)(C)O)=C3N(C)C2=C1OC

InChI Identifier

InChI=1S/C31H29NO9/c1-31(2,36)30-24(23-17(40-30)10-7-14-8-12-20(34)41-28(14)23)22-19(38-5)13-16(33)21-26(22)32(3)25-15(27(21)35)9-11-18(37-4)29(25)39-6/h7-13,24,30,33,36H,1-6H3/t24-,30-/m1/s1

InChI Key

XRRKNHPPSZSNHE-AYWVHJORSA-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
Angular furanocoumarin
Furanocoumarin
Dihydroquinolone
Coumarin
Benzopyran
Dihydroquinoline
1-benzopyran
Coumaran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Pyridine
Benzenoid
Vinylogous acid
Heteroaromatic compound
Tertiary alcohol
Vinylogous amide
Lactone
Oxacycle
Ether
Azacycle
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
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	4.25	ChemAxon
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	123.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	150.18 m³·mol⁻¹	ChemAxon
Polarizability	57.38 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

163027316

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one (NP0222161)

MOL for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)

3D MOL for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)

3D SDF for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)

3D-SDF for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)

PDB for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)

3D PDB for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)

SMILES for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)

INCHI for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)

Structure for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)

3D Structure for NP0222161 (1-hydroxy-4-[(8r,9r)-8-(2-hydroxypropan-2-yl)-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl]-3,5,6-trimethoxy-10-methylacridin-9-one)