NP-MRD: Showing NP-Card for 1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one (NP0293022)

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Record Information

Version

2.0

Created at

2022-09-10 00:49:24 UTC

Updated at

2022-09-10 00:49:24 UTC

NP-MRD ID

NP0293022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one

Description

Neoacrimarine F 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 F is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Neoacrimarine F has been detected, but not quantified in, citrus. 1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one is found in Citrus aurantium. This could make neoacrimarine F a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305432D          

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M  END

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  Mrv0541 05061305432D          

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 29  1  1  0  0  0  0
 29  2  1  0  0  0  0
 29 28  1  0  0  0  0
 30  3  1  0  0  0  0
 30 16  1  0  0  0  0
 30 23  1  0  0  0  0
 31 17  1  0  0  0  0
 32 18  1  0  0  0  0
 33 20  2  0  0  0  0
 34 24  2  0  0  0  0
 35 28  1  0  0  0  0
 36  4  1  0  0  0  0
 36 14  1  0  0  0  0
 37 20  1  0  0  0  0
 37 25  1  0  0  0  0
 38 26  1  0  0  0  0
 38 27  1  0  0  0  0
 39 19  1  0  0  0  0
 39 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0293022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC2C(O)C(C)(C)OC3=C2C2=C(C=CC(=O)O2)C=C3)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H25NO9/c1-29(2)28(35)27(22-19(39-29)9-5-13-6-10-20(33)37-25(13)22)38-26-17(31)8-7-15-23(26)30(3)16-11-14(36-4)12-18(32)21(16)24(15)34/h5-12,27-28,31-32,35H,1-4H3

> <INCHI_KEY>
VMABFFUJXPHEJX-UHFFFAOYSA-N

> <FORMULA>
C29H25NO9

> <MOLECULAR_WEIGHT>
531.5101

> <EXACT_MASS>
531.152931403

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
52.591141295873626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,6-dihydroxy-5-({13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-14-yl}oxy)-3-methoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
4.182456232333333

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.087961892840186

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.405711756697702

> <JCHEM_PKA_STRONGEST_BASIC>
-3.650656410481965

> <JCHEM_POLAR_SURFACE_AREA>
134.99

> <JCHEM_REFRACTIVITY>
140.13369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,6-dihydroxy-5-({13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-14-yl}oxy)-3-methoxy-10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      14.008  -4.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.008  -2.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.438  -7.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.818 -13.186   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.208  -1.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.898  -2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.058 -10.518   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.828  -9.185   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748  -1.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.128  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.898 -10.518   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.898 -13.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.438  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.128 -11.852   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.518 -10.518   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.438 -10.518   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.058  -7.851   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.438 -13.186   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.518  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.898  -5.184   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.208 -11.852   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.748  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748  -9.185   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.748 -11.852   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.208  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.518  -7.851   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.518  -5.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.058  -5.184   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.828  -3.850   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       8.208  -9.185   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0      12.828  -6.517   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.208 -14.519   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.128  -6.517   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      10.518 -13.186   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      13.465  -5.810   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.588 -11.852   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       7.438  -5.184   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       9.748  -6.517   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      12.058  -2.516   0.000  0.00  0.00           O+0
CONECT    1   29                                                            
CONECT    2   29                                                            
CONECT    3   30                                                            
CONECT    4   36                                                            
CONECT    5    9   13                                                       
CONECT    6   10   13                                                       
CONECT    7    8   15                                                       
CONECT    8    7   17                                                       
CONECT    9    5   19                                                       
CONECT   10    6   20                                                       
CONECT   11   14   16                                                       
CONECT   12   14   18                                                       
CONECT   13    5    6   25                                                  
CONECT   14   11   12   36                                                  
CONECT   15    7   23   24                                                  
CONECT   16   11   21   30                                                  
CONECT   17    8   26   31                                                  
CONECT   18   12   21   32                                                  
CONECT   19    9   22   39                                                  
CONECT   20   10   33   37                                                  
CONECT   21   16   18   24                                                  
CONECT   22   19   25   27                                                  
CONECT   23   15   26   30                                                  
CONECT   24   15   21   34                                                  
CONECT   25   13   22   37                                                  
CONECT   26   17   23   38                                                  
CONECT   27   22   28   38                                                  
CONECT   28   27   29   35                                                  
CONECT   29    1    2   28   39                                             
CONECT   30    3   16   23                                                  
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   20                                                            
CONECT   34   24                                                            
CONECT   35   28                                                            
CONECT   36    4   14                                                       
CONECT   37   20   25                                                       
CONECT   38   26   27                                                       
CONECT   39   19   29                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
(+)-Neoacrimarine-F	HMDB

Chemical Formula

C₂₉H₂₅NO₉

Average Mass

531.5101 Da

Monoisotopic Mass

531.15293 Da

IUPAC Name

1,6-dihydroxy-5-({13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-14-yl}oxy)-3-methoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1,6-dihydroxy-5-({13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-14-yl}oxy)-3-methoxy-10-methylacridin-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC2C(O)C(C)(C)OC3=C2C2=C(C=CC(=O)O2)C=C3)=C(O)C=C1

InChI Identifier

InChI=1S/C29H25NO9/c1-29(2)28(35)27(22-19(39-29)9-5-13-6-10-20(33)37-25(13)22)38-26-17(31)8-7-15-23(26)30(3)16-11-14(36-4)12-18(32)21(16)24(15)34/h5-12,27-28,31-32,35H,1-4H3

InChI Key

VMABFFUJXPHEJX-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, 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 aurantium	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
Pyranocoumarin
Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Coumarin
Dihydroquinolone
Chromane
Benzopyran
Dihydroquinoline
1-benzopyran
Anisole
Pyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Pyridine
Pyran
Vinylogous acid
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Lactone
Oxacycle
Azacycle
Ether
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Alcohol
Organic nitrogen compound
Organic oxygen 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	3.88	ALOGPS
logP	4.18	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.41	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	3	ChemAxon
Refractivity	140.13 m³·mol⁻¹	ChemAxon
Polarizability	52.59 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

HMDB0031112

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003120

KNApSAcK ID

C00024224

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

131751137

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one (NP0293022)

MOL for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)

3D MOL for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)

3D SDF for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)

3D-SDF for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)

PDB for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)

3D PDB for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)

SMILES for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)

INCHI for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)

Structure for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)

3D Structure for NP0293022 (1,6-dihydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)