NP-MRD: Showing NP-Card for Citrusinine I (NP0045902)

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Record Information

Version

2.0

Created at

2022-03-17 19:45:07 UTC

Updated at

2022-03-17 19:45:07 UTC

NP-MRD ID

NP0045902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citrusinine I

Description

Citrusinine I 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. Citrusinine I is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Citrusinine I is found, on average, in the highest concentration within sweet oranges. Citrusinine I has also been detected, but not quantified in, citrus. Citrusinine I is found in Atalantia buxifolia, Atalantia monophylla , Atalantia wightii, Citrus aurantium, Citrus hybrid ''Yalaha'', Citrus japonica, Citrus limonia , Citrus grandis , Citrus nobilis , Citrus sinensis, Citrus sinensis var.brasiliensis , Severinia buxifolia and Swinglea glutinosa. This could make citrusinine I a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305112D          

 22 24  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  2  0  0  0  0
 16 14  1  0  0  0  0
 17  1  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 20 15  2  0  0  0  0
 21  2  1  0  0  0  0
 21 11  1  0  0  0  0
 22  3  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C(C(O)=C1)C(=O)C1=C(N2C)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15NO5/c1-17-13-8(5-4-6-9(13)18)15(20)12-10(19)7-11(21-2)16(22-3)14(12)17/h4-7,18-19H,1-3H3

> <INCHI_KEY>
UTEAJHNFBCLZHN-UHFFFAOYSA-N

> <FORMULA>
C16H15NO5

> <MOLECULAR_WEIGHT>
301.294

> <EXACT_MASS>
301.095022595

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.23122656326995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-dihydroxy-3,4-dimethoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.8504817036666665

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.512757700894333

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.126281061705196

> <JCHEM_PKA_STRONGEST_BASIC>
-4.122950473480768

> <JCHEM_POLAR_SURFACE_AREA>
79.23

> <JCHEM_REFRACTIVITY>
80.8466

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-dihydroxy-3,4-dimethoxy-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       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4    9                                                       
CONECT    7   10   11                                                       
CONECT    8    5   13   15                                                  
CONECT    9    6   13   18                                                  
CONECT   10    7   12   19                                                  
CONECT   11    7   16   21                                                  
CONECT   12   10   14   15                                                  
CONECT   13    8    9   17                                                  
CONECT   14   12   16   17                                                  
CONECT   15    8   12   20                                                  
CONECT   16   11   14   22                                                  
CONECT   17    1   13   14                                                  
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   15                                                            
CONECT   21    2   11                                                       
CONECT   22    3   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
1,5-Dihydroxy-3,4-dimethoxy-10-methyl-9(10H)-acridinone	HMDB
1,5-Dihydroxy-3,4-dimethoxy-10-methylacridone	HMDB
Citrusinine-I	HMDB
Citrusinine I	MeSH

Chemical Formula

C₁₆H₁₅NO₅

Average Mass

301.2940 Da

Monoisotopic Mass

301.09502 Da

IUPAC Name

1,5-dihydroxy-3,4-dimethoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1,5-dihydroxy-3,4-dimethoxy-10-methylacridin-9-one

CAS Registry Number

86680-32-2

SMILES

COC1=C(OC)C2=C(C(O)=C1)C(=O)C1=C(N2C)C(O)=CC=C1

InChI Identifier

InChI=1S/C16H15NO5/c1-17-13-8(5-4-6-9(13)18)15(20)12-10(19)7-11(21-2)16(22-3)14(12)17/h4-7,18-19H,1-3H3

InChI Key

UTEAJHNFBCLZHN-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, 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
Atalantia buxifolia	LOTUS Database	35616633
Atalantia monophylla	Plant	KNApSAcK
Atalantia wightii	Plant	KNApSAcK
Citrus aurantium	LOTUS Database	35616633
Citrus hybrid ''Yalaha''	Plant	KNApSAcK
Citrus japonica	LOTUS Database	35616633
Citrus limonia	Plant	KNApSAcK
Citrus maxima	Plant	KNApSAcK
Citrus nobilis	Plant	KNApSAcK
Citrus sinensis	LOTUS Database	35616633
Citrus sinensis var.brasiliensis	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Severinia buxifolia	Plant	KNApSAcK
Swinglea glutinosa	-	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
Dihydroquinolone
8-hydroxyquinoline
Dihydroquinoline
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous acid
Vinylogous amide
Ether
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen 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	2.49	ALOGPS
logP	2.85	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.85 m³·mol⁻¹	ChemAxon
Polarizability	30.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030374

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002223

KNApSAcK ID

C00024249

Chemspider ID

4589521

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5487772

PDB ID

Not Available

ChEBI ID

542878

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Citrusinine I (NP0045902)

MOL for NP0045902 (Citrusinine I)

3D MOL for NP0045902 (Citrusinine I)

3D SDF for NP0045902 (Citrusinine I)

3D-SDF for NP0045902 (Citrusinine I)

PDB for NP0045902 (Citrusinine I)

3D PDB for NP0045902 (Citrusinine I)

SMILES for NP0045902 (Citrusinine I)

INCHI for NP0045902 (Citrusinine I)

Structure for NP0045902 (Citrusinine I)

3D Structure for NP0045902 (Citrusinine I)