NP-MRD: Showing NP-Card for Junosidine (NP0083561)

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Record Information

Version

2.0

Created at

2022-04-29 04:34:01 UTC

Updated at

2022-04-29 04:34:01 UTC

NP-MRD ID

NP0083561

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Junosidine

Description

Junosidine 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. Junosidine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Junosidine has been detected, but not quantified in, citrus. Junosidine is found in Citrus junos . This could make junosidine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -5.5111   -0.7827    1.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1876   -0.5948    1.3203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646    0.0013    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0617    0.4117   -0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8418    1.0068   -1.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    1.2136   -2.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    0.8052   -1.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494    1.0234   -2.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0383    1.5671   -3.2239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1770    0.6185   -1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1148    0.8098   -1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    1.4122   -3.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1931    0.4100   -1.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0416   -0.1930    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7261   -0.3788    0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649    0.0177   -0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014   -0.1970    0.3818 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8376   -0.8013    1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6783    0.1931   -0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1120   -0.6011    0.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4346   -0.4402    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145   -1.8500    0.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2479    0.3513    1.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5810    0.2047   -0.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5703    0.5916   -1.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0341    0.1976    1.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0951   -1.4459    1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4726   -1.2239    2.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0427    0.2337   -0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7089    1.3112   -2.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3982    1.6796   -3.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1071    1.6282   -3.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5850   -0.8454    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -1.0975    2.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988   -1.7831    1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500   -0.0467    2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0584   -2.3801    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3454   -2.3972   -0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0087   -1.7905   -0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267    1.3771    1.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2737    0.4591    1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3045   -0.1375    2.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750    0.3914   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042    1.0710   -2.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 19  2  0
 19 17  1  0
 17 18  1  0
 17 16  1  0
 16 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 25  1  0
 25 24  2  0
 24 21  1  0
 21 22  1  0
 21 23  1  0
 21 20  1  0
 20 14  1  0
 14 15  2  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  7 19  1  0
 15 16  1  0
 14 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 12 32  1  0
 25 44  1  0
 24 43  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
 15 33  1  0
  6 31  1  0
  5 30  1  0
  4 29  1  0
M  END


  Mrv1652309272007252D          

 25 28  0  0  0  0            999 V2000
 9998.9567 9998.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.529810001.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.678210001.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.956710001.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3823 9998.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.331710000.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.801610000.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.381810000.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3817 9998.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.529910000.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.815410000.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8153 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5298 9998.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.956110000.5743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.241610000.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2416 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9561 9998.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6706 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.670610000.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.807610000.5743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.093110000.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0931 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8076 9998.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5221 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.522110000.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 10  2  1  0  0  0  0
  9  5  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 21 22  1  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
 20 21  1  0  0  0  0
 20 25  1  0  0  0  0
 25  7  1  0  0  0  0
 25  6  1  0  0  0  0
 21  8  2  0  0  0  0
  9 22  2  0  0  0  0
 14  4  1  0  0  0  0
  1 17  2  0  0  0  0
  8 19  1  0  0  0  0
 18  9  1  0  0  0  0
 15 10  2  0  0  0  0
 13 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0083561

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO4/c1-20(2)9-8-11-15(25-20)10-13-16(18(11)22)19(23)12-6-5-7-14(24-4)17(12)21(13)3/h5-10,22H,1-4H3

> <INCHI_KEY>
AUWXWUDANKEVNS-UHFFFAOYSA-N

> <FORMULA>
C20H19NO4

> <MOLECULAR_WEIGHT>
337.3692

> <EXACT_MASS>
337.131408101

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.44602726982549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-10-methoxy-2,2,11-trimethyl-6,11-dihydro-2H-1-oxa-11-azatetracen-6-one

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.212341692999999

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.695617464133832

> <JCHEM_PKA_STRONGEST_BASIC>
-4.589741933676475

> <JCHEM_POLAR_SURFACE_AREA>
59.0

> <JCHEM_REFRACTIVITY>
96.79589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-10-methoxy-2,2,11-trimethyl-1-oxa-11-azatetracen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8664.7198663.107   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8662.0568669.291   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8660.4668670.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.7198669.291   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8667.3808663.107   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8672.8868666.708   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.8968668.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.3798667.738   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.3798664.658   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.0568667.738   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.7228666.968   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8660.7228665.429   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.0568664.658   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8664.7188667.739   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8663.3848666.969   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.3848665.429   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.7188664.659   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.0528665.429   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.0528666.969   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8670.0418667.739   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8668.7078666.969   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.7078665.429   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.0418664.659   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.3758665.429   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.3758666.969   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    3   10                                                       
CONECT    3    2                                                            
CONECT    4   14                                                            
CONECT    5    9                                                            
CONECT    6   25                                                            
CONECT    7   25                                                            
CONECT    8   21   19                                                       
CONECT    9    5   22   18                                                  
CONECT   10   11    2   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   16                                                       
CONECT   14   15   19    4                                                  
CONECT   15   16   14   10                                                  
CONECT   16   15   17   13                                                  
CONECT   17   16   18    1                                                  
CONECT   18   17   19    9                                                  
CONECT   19   18   14    8                                                  
CONECT   20   21   25                                                       
CONECT   21   22   20    8                                                  
CONECT   22   21   23    9                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20    7    6                                             
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
2,11-Dihydro-5-hydroxy-10-methoxy-2,2,11-trimethyl-6H-pyrano[3,2-b]acridin-6-one, 9ci	HMDB

Chemical Formula

C₂₀H₁₉NO₄

Average Mass

337.3692 Da

Monoisotopic Mass

337.13141 Da

IUPAC Name

5-hydroxy-10-methoxy-2,2,11-trimethyl-6,11-dihydro-2H-1-oxa-11-azatetracen-6-one

Traditional Name

5-hydroxy-10-methoxy-2,2,11-trimethyl-1-oxa-11-azatetracen-6-one

CAS Registry Number

Not Available

SMILES

COC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C1

InChI Identifier

InChI=1S/C20H19NO4/c1-20(2)9-8-11-15(25-20)10-13-16(18(11)22)19(23)12-6-5-7-14(24-4)17(12)21(13)3/h5-10,22H,1-4H3

InChI Key

AUWXWUDANKEVNS-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
Citrus junos	Plant	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
Chromenopyridine
2,2-dimethyl-1-benzopyran
Dihydroquinolone
Benzopyran
Dihydroquinoline
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Oxacycle
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen 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	3.64	ALOGPS
logP	4.21	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.8 m³·mol⁻¹	ChemAxon
Polarizability	36.45 Å³	ChemAxon
Number of Rings	4	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

HMDB0029827

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001039

KNApSAcK ID

Not Available

Chemspider ID

9834814

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11660079

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Junosidine (NP0083561)

MOL for NP0083561 (Junosidine)

3D MOL for NP0083561 (Junosidine)

3D SDF for NP0083561 (Junosidine)

3D-SDF for NP0083561 (Junosidine)

PDB for NP0083561 (Junosidine)

3D PDB for NP0083561 (Junosidine)

SMILES for NP0083561 (Junosidine)

INCHI for NP0083561 (Junosidine)

Structure for NP0083561 (Junosidine)

3D Structure for NP0083561 (Junosidine)