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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:41 UTC

Update Date

2022-03-07 02:52:07 UTC

HMDB ID

HMDB0029324

Secondary Accession Numbers

HMDB29324

Metabolite Identification

Common Name

Citpressine II

Description

Citpressine II 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. Based on a literature review very few articles have been published on Citpressine II.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0029324
     RDKit          3D
Citpressine II
 40 42  0  0  0  0  0  0  0  0999 V2000
    5.0930   -0.7699   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0329   -0.9090   -0.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8264   -0.7054    0.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413   -0.8343    1.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624   -0.6384    2.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -0.7709    3.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.3010    1.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2649   -0.1278    2.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614   -0.2614    3.4959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615    0.1881    1.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171    0.3438    2.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964    0.6492    1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1824    0.7910    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208    1.0940   -0.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5456    1.2680    0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    0.6263   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    0.7738   -1.8505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -0.4252   -2.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.3275    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586    0.1577   -0.5263 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576    0.3981   -1.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -0.1647    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022   -0.3690   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6412    0.2151   -2.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1364   -0.8472   -2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072   -1.6241   -2.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350   -1.0994    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -1.0144    4.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0221    0.2285    3.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1329    0.7819    2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7725    0.3815    0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3581    1.3711   -0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4606    2.1646    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4991   -0.4615   -2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9930   -1.3149   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235   -0.4139   -3.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174    0.8068   -2.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4966   -2.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1267    1.2694   -2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -0.2874   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23  3  1  0
 22  7  1  0
 19 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 23 40  1  0
M  END


  Mrv0541 02241210522D          

 23 25  0  0  0  0            999 V2000
   -1.7733    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0308   -0.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0308    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.2067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5158   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733   -1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0308   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -2.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -2.6808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5158   -2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158   -0.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0308    2.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    2.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 21  1  0  0  0  0
  3  4  2  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  2  0  0  0  0
 10 11  1  0  0  0  0
 10 18  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029324

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO5/c1-18-11-7-9(21-2)8-12(19)14(11)16(20)10-5-6-13(22-3)17(23-4)15(10)18/h5-8,19H,1-4H3

> <INCHI_KEY>
CHCYJKZBXNSGCG-UHFFFAOYSA-N

> <FORMULA>
C17H17NO5

> <MOLECULAR_WEIGHT>
315.3206

> <EXACT_MASS>
315.110672659

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
32.66379001421376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-3,5,6-trimethoxy-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.996375759666666

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.034219926297245

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6112587911556546

> <JCHEM_POLAR_SURFACE_AREA>
68.23

> <JCHEM_REFRACTIVITY>
85.3289

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-3,5,6-trimethoxy-10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029324
     RDKit          3D
Citpressine II
 40 42  0  0  0  0  0  0  0  0999 V2000
    5.0930   -0.7699   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0329   -0.9090   -0.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8264   -0.7054    0.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413   -0.8343    1.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624   -0.6384    2.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -0.7709    3.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.3010    1.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2649   -0.1278    2.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614   -0.2614    3.4959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615    0.1881    1.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171    0.3438    2.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964    0.6492    1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1824    0.7910    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208    1.0940   -0.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5456    1.2680    0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    0.6263   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    0.7738   -1.8505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -0.4252   -2.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.3275    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586    0.1577   -0.5263 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576    0.3981   -1.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -0.1647    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022   -0.3690   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6412    0.2151   -2.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1364   -0.8472   -2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072   -1.6241   -2.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350   -1.0994    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -1.0144    4.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0221    0.2285    3.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1329    0.7819    2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7725    0.3815    0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3581    1.3711   -0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4606    2.1646    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4991   -0.4615   -2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9930   -1.3149   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235   -0.4139   -3.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174    0.8068   -2.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4966   -2.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1267    1.2694   -2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -0.2874   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23  3  1  0
 22  7  1  0
 19 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 23 40  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.310   1.924   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.310   0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.924  -0.386   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.692   0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.692   1.924   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.924   2.694   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.078   0.384   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.692  -0.386   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.692  -1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.078  -2.694   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.310  -1.924   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.696  -2.694   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.310  -2.694   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.924  -1.924   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.692  -2.694   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.692  -4.234   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.692  -5.004   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.078  -4.234   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.310  -5.004   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.696  -4.234   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.696  -0.386   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.924   4.234   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.692   5.004   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   22                                                  
CONECT    7    8                                                            
CONECT    8    4    7    9                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14    3   13   15                                                  
CONECT   15    9   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   10   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    2                                                            
CONECT   22    6   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0029324
HETATM    1  C1  UNL     1       5.093  -0.770  -1.831  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.033  -0.909  -0.425  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.826  -0.705   0.245  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.741  -0.834   1.611  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.562  -0.638   2.290  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.480  -0.771   3.677  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.442  -0.301   1.549  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.265  -0.128   2.248  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.261  -0.261   3.496  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.861   0.188   1.525  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.017   0.344   2.236  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.196   0.649   1.587  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.182   0.791   0.217  1.00  0.00           C  
HETATM   14  O4  UNL     1      -4.321   1.094  -0.500  1.00  0.00           O  
HETATM   15  C11 UNL     1      -5.546   1.268   0.170  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.981   0.626  -0.496  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.047   0.774  -1.851  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.391  -0.425  -2.581  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.802   0.327   0.132  1.00  0.00           C  
HETATM   20  N1  UNL     1       0.359   0.158  -0.526  1.00  0.00           N  
HETATM   21  C15 UNL     1       0.458   0.398  -1.943  1.00  0.00           C  
HETATM   22  C16 UNL     1       1.509  -0.165   0.164  1.00  0.00           C  
HETATM   23  C17 UNL     1       2.702  -0.369  -0.482  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.641   0.215  -2.112  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.136  -0.847  -2.189  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.507  -1.624  -2.255  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.635  -1.099   2.170  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.276  -1.014   4.241  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.022   0.228   3.327  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.133   0.782   2.113  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.773   0.382   0.799  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.358   1.371  -0.561  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.461   2.165   0.807  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.499  -0.462  -2.618  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.993  -1.315  -2.052  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.923  -0.414  -3.582  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.517   0.807  -2.152  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.444  -0.497  -2.577  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.127   1.269  -2.316  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.744  -0.287  -1.556  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   27
CONECT    5    6    7    7
CONECT    6   28
CONECT    7    8   22
CONECT    8    9    9   10
CONECT   10   11   11   19
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   16
CONECT   14   15
CONECT   15   31   32   33
CONECT   16   17   19   19
CONECT   17   18
CONECT   18   34   35   36
CONECT   19   20
CONECT   20   21   22
CONECT   21   37   38   39
CONECT   22   23   23
CONECT   23   40
END

HMDB0029324
     RDKit          3D
Citpressine II
 40 42  0  0  0  0  0  0  0  0999 V2000
    5.0930   -0.7699   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0329   -0.9090   -0.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8264   -0.7054    0.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413   -0.8343    1.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624   -0.6384    2.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4803   -0.7709    3.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -0.3010    1.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2649   -0.1278    2.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614   -0.2614    3.4959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615    0.1881    1.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171    0.3438    2.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964    0.6492    1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1824    0.7910    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3208    1.0940   -0.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5456    1.2680    0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    0.6263   -0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    0.7738   -1.8505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -0.4252   -2.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    0.3275    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586    0.1577   -0.5263 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576    0.3981   -1.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -0.1647    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022   -0.3690   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6412    0.2151   -2.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1364   -0.8472   -2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072   -1.6241   -2.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350   -1.0994    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -1.0144    4.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0221    0.2285    3.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1329    0.7819    2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7725    0.3815    0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3581    1.3711   -0.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4606    2.1646    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4991   -0.4615   -2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9930   -1.3149   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235   -0.4139   -3.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174    0.8068   -2.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4966   -2.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1267    1.2694   -2.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -0.2874   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23  3  1  0
 22  7  1  0
 19 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 23 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Hydroxy-3,5,6-trimethoxy-10-methylacridone	HMDB

Chemical Formula

C₁₇H₁₇NO₅

Average Molecular Weight

315.3206

Monoisotopic Molecular Weight

315.110672659

IUPAC Name

1-hydroxy-3,5,6-trimethoxy-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1-hydroxy-3,5,6-trimethoxy-10-methylacridin-9-one

CAS Registry Number

81525-59-9

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC)=C(OC)C=C1

InChI Identifier

InChI=1S/C17H17NO5/c1-18-11-7-9(21-2)8-12(19)14(11)16(20)10-5-6-13(22-3)17(23-4)15(10)18/h5-8,19H,1-4H3

InChI Key

CHCYJKZBXNSGCG-UHFFFAOYSA-N

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
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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029324)
Cytoplasm (HMDB: HMDB0029324)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029324)

Source

Endogenous

Endogenous (HMDB: HMDB0029324)

Plant

Plant (HMDB: HMDB0029324)

Exogenous

Food

Food (HMDB: HMDB0029324)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Exogenous (HMDB: HMDB0029324)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	168 - 170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18.33 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	2.39	ALOGPS
logP	3	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.03	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.33 m³·mol⁻¹	ChemAxon
Polarizability	32.66 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.788	31661259
DarkChem	[M-H]-	175.293	31661259
DeepCCS	[M+H]+	176.563	30932474
DeepCCS	[M-H]-	174.205	30932474
DeepCCS	[M-2H]-	208.458	30932474
DeepCCS	[M+Na]+	183.685	30932474
AllCCS	[M+H]+	171.8	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	175.0	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	177.7	32859911
AllCCS	[M+Na-2H]-	177.3	32859911
AllCCS	[M+HCOO]-	176.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.99 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6039 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.21 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1931.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	227.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	130.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	416.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	395.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	173.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	750.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	334.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1122.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	312.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	509.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	458.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	30.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citpressine II	COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC)=C(OC)C=C1	3829.6	Standard polar	33892256
Citpressine II	COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC)=C(OC)C=C1	2627.7	Standard non polar	33892256
Citpressine II	COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC)=C(OC)C=C1	3143.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citpressine II,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=C(OC)C(OC)=C3N(C)C2=C1	3012.8	Semi standard non polar	33892256
Citpressine II,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C(OC)C(OC)=C3N(C)C2=C1	3199.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Citpressine II GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0192000000-f923154a770ffbe2277f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citpressine II GC-MS (1 TMS) - 70eV, Positive	splash10-00di-1019000000-0008a863737a55addb0a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citpressine II GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citpressine II GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 10V, Positive-QTOF	splash10-014i-0009000000-856067abfa60f0563695	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 20V, Positive-QTOF	splash10-014i-0029000000-91c412bb71cf8011492f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 40V, Positive-QTOF	splash10-05nr-0190000000-15f6b007c75fd3759209	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 10V, Negative-QTOF	splash10-03di-0009000000-2291160fd84f263b6f26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 20V, Negative-QTOF	splash10-03di-0029000000-1db0b9eeed2590610bc8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 40V, Negative-QTOF	splash10-004r-1980000000-ec79694899fae071730a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 10V, Positive-QTOF	splash10-014i-0009000000-429ba89e84cbd8f21250	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 20V, Positive-QTOF	splash10-014i-0009000000-429ba89e84cbd8f21250	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 40V, Positive-QTOF	splash10-0g5c-0190000000-c99057f5f39ff23c093a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 10V, Negative-QTOF	splash10-03di-0009000000-a36aafc9dc49db71788f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 20V, Negative-QTOF	splash10-03di-0009000000-a36aafc9dc49db71788f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citpressine II 40V, Negative-QTOF	splash10-0zn9-0190000000-893ff862ecafacdf3f64	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000385

KNApSAcK ID

C00052241

Chemspider ID

4592126

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5494828

PDB ID

Not Available

ChEBI ID

172546

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1808391

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Citpressine II (HMDB0029324)

MOL for HMDB0029324 (Citpressine II)

3D MOL for HMDB0029324 (Citpressine II)

3D SDF for HMDB0029324 (Citpressine II)

3D-SDF for HMDB0029324 (Citpressine II)

PDB for HMDB0029324 (Citpressine II)

3D PDB for HMDB0029324 (Citpressine II)

SMILES for HMDB0029324 (Citpressine II)

INCHI for HMDB0029324 (Citpressine II)

Structure for HMDB0029324 (Citpressine II)

3D Structure for HMDB0029324 (Citpressine II)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra