NP-MRD: Showing NP-Card for 1-hydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one (NP0281932)

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Record Information

Version

2.0

Created at

2022-09-09 08:33:57 UTC

Updated at

2022-09-09 08:33:57 UTC

NP-MRD ID

NP0281932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-hydroxy-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 G belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Neoacrimarine G is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Neoacrimarine G has been detected, but not quantified in, citrus. 1-hydroxy-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 paradisi. This could make neoacrimarine g a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305452D          

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  Mrv0541 05061305452D          

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 35 15  1  0  0  0  0
 36 20  1  0  0  0  0
 36 27  1  0  0  0  0
 37 21  1  0  0  0  0
 37 26  1  0  0  0  0
 38 19  1  0  0  0  0
 38 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281932

> <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)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H25NO8/c1-29(2)28(34)27(23-19(38-29)10-8-14-9-11-21(32)37-26(14)23)36-20-7-5-6-16-24(20)30(3)17-12-15(35-4)13-18(31)22(17)25(16)33/h5-13,27-28,31,34H,1-4H3

> <INCHI_KEY>
MNOCITGIWBOSNH-UHFFFAOYSA-N

> <FORMULA>
C29H25NO8

> <MOLECULAR_WEIGHT>
515.5107

> <EXACT_MASS>
515.158016781

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
51.67871366542944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxy-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>
3.93

> <JCHEM_LOGP>
4.486021554

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.828898662339551

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.029598946310424

> <JCHEM_PKA_STRONGEST_BASIC>
-3.031482971822874

> <JCHEM_POLAR_SURFACE_AREA>
114.76000000000002

> <JCHEM_REFRACTIVITY>
138.15279999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-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       8.673  -4.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673  -2.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -7.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.516 -13.186   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494  -9.185   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724 -10.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724  -7.851   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.564 -10.518   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564 -13.186   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.206 -11.852   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184 -10.518   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104 -10.518   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104 -13.186   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.184  -7.851   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.874 -11.852   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -9.185   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414 -11.852   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       2.874  -9.185   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       2.874 -14.519   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.184 -13.186   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       7.494  -6.517   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.746 -11.852   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       4.414  -6.517   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.104  -5.184   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       6.724  -2.516   0.000  0.00  0.00           O+0
CONECT    1   29                                                            
CONECT    2   29                                                            
CONECT    3   30                                                            
CONECT    4   35                                                            
CONECT    5    6    7                                                       
CONECT    6    5   16                                                       
CONECT    7    5   20                                                       
CONECT    8   10   14                                                       
CONECT    9   11   14                                                       
CONECT   10    8   19                                                       
CONECT   11    9   21                                                       
CONECT   12   15   17                                                       
CONECT   13   15   18                                                       
CONECT   14    8    9   26                                                  
CONECT   15   12   13   35                                                  
CONECT   16    6   24   25                                                  
CONECT   17   12   22   30                                                  
CONECT   18   13   22   31                                                  
CONECT   19   10   23   38                                                  
CONECT   20    7   24   36                                                  
CONECT   21   11   32   37                                                  
CONECT   22   17   18   25                                                  
CONECT   23   19   26   27                                                  
CONECT   24   16   20   30                                                  
CONECT   25   16   22   33                                                  
CONECT   26   14   23   37                                                  
CONECT   27   23   28   36                                                  
CONECT   28   27   29   34                                                  
CONECT   29    1    2   28   38                                             
CONECT   30    3   17   24                                                  
CONECT   31   18                                                            
CONECT   32   21                                                            
CONECT   33   25                                                            
CONECT   34   28                                                            
CONECT   35    4   15                                                       
CONECT   36   20   27                                                       
CONECT   37   21   26                                                       
CONECT   38   19   29                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
(+)-Neoacrimarine-g	HMDB

Chemical Formula

C₂₉H₂₅NO₈

Average Mass

515.5107 Da

Monoisotopic Mass

515.15802 Da

IUPAC Name

1-hydroxy-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-hydroxy-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)=CC=C1

InChI Identifier

InChI=1S/C29H25NO8/c1-29(2)28(34)27(23-19(38-29)10-8-14-9-11-21(32)37-26(14)23)36-20-7-5-6-16-24(20)30(3)17-12-15(35-4)13-18(31)22(17)25(16)33/h5-13,27-28,31,34H,1-4H3

InChI Key

MNOCITGIWBOSNH-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 paradisi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.93	ALOGPS
logP	4.49	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	10.03	ChemAxon
pKa (Strongest Basic)	-3	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	138.15 m³·mol⁻¹	ChemAxon
Polarizability	51.68 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

HMDB0031135

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003146

KNApSAcK ID

C00024225

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

131751141

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-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one (NP0281932)

MOL for NP0281932 (1-hydroxy-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 NP0281932 (1-hydroxy-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 NP0281932 (1-hydroxy-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 NP0281932 (1-hydroxy-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 NP0281932 (1-hydroxy-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 NP0281932 (1-hydroxy-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 NP0281932 (1-hydroxy-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 NP0281932 (1-hydroxy-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 NP0281932 (1-hydroxy-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 NP0281932 (1-hydroxy-5-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-3-methoxy-10-methylacridin-9-one)