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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:55:27 UTC

Update Date

2022-03-07 02:55:50 UTC

HMDB ID

HMDB0038599

Secondary Accession Numbers

HMDB38599

Metabolite Identification

Common Name

Acrimarine H

Description

Acrimarine H 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. Acrimarine H has been detected, but not quantified in, citrus. This could make acrimarine H a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Acrimarine H.

Structure

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


  Mrv0541 01291301242D          

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M  END

HMDB0038599
     RDKit          3D
Acrimarine H
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M  END


  Mrv0541 01291301242D          

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 29 33  2  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  0  0  0  0
 18 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038599

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(O)C2=C(C=C1OC)N(C)C1=C(C=CC=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H27NO7/c1-15(2)11-19(18-12-16-9-10-25(33)38-22(16)14-23(18)36-4)26-24(37-5)13-20-27(30(26)35)29(34)17-7-6-8-21(32)28(17)31(20)3/h6-14,19,32,35H,1-5H3

> <INCHI_KEY>
LUTVFOXEXBZKQE-UHFFFAOYSA-N

> <FORMULA>
C30H27NO7

> <MOLECULAR_WEIGHT>
513.5379

> <EXACT_MASS>
513.178752223

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
54.398787617101966

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,5-dihydroxy-3-methoxy-2-[1-(7-methoxy-2-oxo-2H-chromen-6-yl)-3-methylbut-2-en-1-yl]-10-methyl-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
4.91

> <JCHEM_LOGP>
5.809985571333332

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.893809210236087

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.082886335312189

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0643090100423955

> <JCHEM_POLAR_SURFACE_AREA>
105.53000000000002

> <JCHEM_REFRACTIVITY>
145.2236

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-dihydroxy-3-methoxy-2-[1-(7-methoxy-2-oxochromen-6-yl)-3-methylbut-2-en-1-yl]-10-methylacridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038599
     RDKit          3D
Acrimarine H
 65 69  0  0  0  0  0  0  0  0999 V2000
   -1.8413   -0.2210    3.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589   -0.3714    2.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3864    0.5389    1.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847    1.5840    2.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7265    2.5178    1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002    3.5264    1.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0116    4.4167    1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6539    5.3793    1.5837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0074    4.3825   -0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3254    3.3599   -0.9601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924    2.4394   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9824    1.3776   -0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353    0.4353    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -0.6466   -0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831   -1.9369   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -2.7426   -0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0988   -2.4252   -2.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3968   -4.0325   -0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488   -0.5850   -0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5444   -1.7183   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707   -2.9707    0.0132 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221   -4.1558    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9373   -1.7107    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146   -0.5198   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.6319   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5085    0.6389   -0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2543    1.7344   -0.7861 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5470    1.8050   -0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    2.8870   -0.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9185    1.8262   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    3.0141   -0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802    3.0678   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417    1.9171    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9887    0.6923    0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172   -0.4471    0.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6318    0.6581    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9610   -0.5240    0.1322 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334   -1.6975    0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713   -0.4546    4.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823   -0.8759    4.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088    0.8030    4.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586    1.7150    3.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5165    5.1247   -0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2544    3.2334   -2.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651    1.3300   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -0.6150   -1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -2.2081    0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -3.0796   -2.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4984   -1.3800   -2.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1853   -2.4778   -2.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -3.8956    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2579   -4.3783   -0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5800   -4.7793   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376   -4.9763    0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1193   -4.0949    1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3390   -4.3340   -0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058   -2.6549    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0623    2.6652   -0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0289    3.9034   -0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5070    4.0128   -0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186    1.9016    0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7130   -0.3785    0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199   -1.6603    1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691   -2.5726    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -1.9987   -0.3736 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
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 14 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 25 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 36 37  1  0
 37 38  1  0
 13  3  1  0
 26 19  1  0
 36 30  1  0
 11  5  2  0
 37 24  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  4 42  1  0
  9 43  1  0
 10 44  1  0
 12 45  1  0
 14 46  1  0
 15 47  1  0
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 27 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 35 62  1  0
 38 63  1  0
 38 64  1  0
 38 65  1  0
M  END

HEADER    PROTEIN                                 29-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JAN-13         0                                  
HETATM    1  C   UNK     0      -7.187  -9.313   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.520 -10.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.520 -11.623   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.187 -12.393   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.853 -11.623   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.853 -10.083   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.519  -9.313   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -4.519 -12.393   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -3.186 -11.623   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.186 -10.083   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.852  -9.313   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.852 -12.393   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.518 -11.623   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.518 -10.083   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.815  -9.313   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.149  -7.003   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.815  -7.773   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.149 -10.083   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.187 -13.933   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.519 -13.933   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.519  -7.773   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.852  -7.773   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.815 -12.393   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.149 -11.623   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.815  -4.693   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.518  -5.463   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.518  -7.003   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.149  -5.463   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.518  -2.383   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.852  -3.153   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.852  -4.693   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.815  -3.153   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.518  -0.843   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.483  -7.773   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.816  -7.003   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.689 -10.083   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.459 -11.417   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.459  -8.750   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10   21                                                  
CONECT    8    5    9   20                                                  
CONECT    9    8   10   12                                                  
CONECT   10    7   11    9                                                  
CONECT   11   10   14   22                                                  
CONECT   12    9   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   11   15                                                  
CONECT   15   14   17   18                                                  
CONECT   16   28   17   34                                                  
CONECT   17   15   16   27                                                  
CONECT   18   15   36                                                       
CONECT   19    4                                                            
CONECT   20    8                                                            
CONECT   21    7                                                            
CONECT   22   11                                                            
CONECT   23   13   24                                                       
CONECT   24   23                                                            
CONECT   25   28   26   32                                                  
CONECT   26   27   31   25                                                  
CONECT   27   17   26                                                       
CONECT   28   16   25                                                       
CONECT   29   30   32   33                                                  
CONECT   30   29   31                                                       
CONECT   31   26   30                                                       
CONECT   32   25   29                                                       
CONECT   33   29                                                            
CONECT   34   16   35                                                       
CONECT   35   34                                                            
CONECT   36   18   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

COMPND    HMDB0038599
HETATM    1  C1  UNL     1      -1.841  -0.221   3.703  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.759  -0.371   2.319  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.386   0.539   1.474  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.085   1.584   2.034  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.726   2.518   1.248  1.00  0.00           C  
HETATM    6  O2  UNL     1      -4.400   3.526   1.781  1.00  0.00           O  
HETATM    7  C5  UNL     1      -5.012   4.417   1.039  1.00  0.00           C  
HETATM    8  O3  UNL     1      -5.654   5.379   1.584  1.00  0.00           O  
HETATM    9  C6  UNL     1      -5.007   4.382  -0.339  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.325   3.360  -0.960  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.692   2.439  -0.126  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.982   1.378  -0.647  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.335   0.435   0.110  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.616  -0.647  -0.559  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.183  -1.937  -0.087  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.856  -2.743  -0.894  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.099  -2.425  -2.330  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.397  -4.033  -0.352  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.149  -0.585  -0.389  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.544  -1.718  -0.113  1.00  0.00           C  
HETATM   21  O4  UNL     1      -0.071  -2.971   0.013  1.00  0.00           O  
HETATM   22  C18 UNL     1       0.622  -4.156   0.298  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.937  -1.711   0.066  1.00  0.00           C  
HETATM   24  C20 UNL     1       2.615  -0.520  -0.043  1.00  0.00           C  
HETATM   25  C21 UNL     1       1.879   0.632  -0.328  1.00  0.00           C  
HETATM   26  C22 UNL     1       0.509   0.639  -0.506  1.00  0.00           C  
HETATM   27  O5  UNL     1      -0.254   1.734  -0.786  1.00  0.00           O  
HETATM   28  C23 UNL     1       2.547   1.805  -0.435  1.00  0.00           C  
HETATM   29  O6  UNL     1       2.005   2.887  -0.683  1.00  0.00           O  
HETATM   30  C24 UNL     1       3.919   1.826  -0.261  1.00  0.00           C  
HETATM   31  C25 UNL     1       4.623   3.014  -0.365  1.00  0.00           C  
HETATM   32  C26 UNL     1       5.980   3.068  -0.198  1.00  0.00           C  
HETATM   33  C27 UNL     1       6.642   1.917   0.076  1.00  0.00           C  
HETATM   34  C28 UNL     1       5.989   0.692   0.194  1.00  0.00           C  
HETATM   35  O7  UNL     1       6.717  -0.447   0.474  1.00  0.00           O  
HETATM   36  C29 UNL     1       4.632   0.658   0.024  1.00  0.00           C  
HETATM   37  N1  UNL     1       3.961  -0.524   0.132  1.00  0.00           N  
HETATM   38  C30 UNL     1       4.733  -1.698   0.430  1.00  0.00           C  
HETATM   39  H1  UNL     1      -2.871  -0.455   4.105  1.00  0.00           H  
HETATM   40  H2  UNL     1      -1.082  -0.876   4.217  1.00  0.00           H  
HETATM   41  H3  UNL     1      -1.609   0.803   4.073  1.00  0.00           H  
HETATM   42  H4  UNL     1      -3.159   1.715   3.117  1.00  0.00           H  
HETATM   43  H5  UNL     1      -5.516   5.125  -0.937  1.00  0.00           H  
HETATM   44  H6  UNL     1      -4.254   3.233  -2.027  1.00  0.00           H  
HETATM   45  H7  UNL     1      -2.965   1.330  -1.747  1.00  0.00           H  
HETATM   46  H8  UNL     1      -1.785  -0.615  -1.671  1.00  0.00           H  
HETATM   47  H9  UNL     1      -2.036  -2.208   0.947  1.00  0.00           H  
HETATM   48  H10 UNL     1      -3.899  -3.080  -2.722  1.00  0.00           H  
HETATM   49  H11 UNL     1      -3.498  -1.380  -2.454  1.00  0.00           H  
HETATM   50  H12 UNL     1      -2.185  -2.478  -2.948  1.00  0.00           H  
HETATM   51  H13 UNL     1      -3.687  -3.896   0.693  1.00  0.00           H  
HETATM   52  H14 UNL     1      -4.258  -4.378  -0.965  1.00  0.00           H  
HETATM   53  H15 UNL     1      -2.580  -4.779  -0.496  1.00  0.00           H  
HETATM   54  H16 UNL     1      -0.138  -4.976   0.279  1.00  0.00           H  
HETATM   55  H17 UNL     1       1.119  -4.095   1.290  1.00  0.00           H  
HETATM   56  H18 UNL     1       1.339  -4.334  -0.537  1.00  0.00           H  
HETATM   57  H19 UNL     1       2.406  -2.655   0.280  1.00  0.00           H  
HETATM   58  H20 UNL     1      -0.062   2.665  -0.915  1.00  0.00           H  
HETATM   59  H21 UNL     1       4.029   3.903  -0.589  1.00  0.00           H  
HETATM   60  H22 UNL     1       6.507   4.013  -0.286  1.00  0.00           H  
HETATM   61  H23 UNL     1       7.719   1.902   0.218  1.00  0.00           H  
HETATM   62  H24 UNL     1       7.713  -0.378   0.598  1.00  0.00           H  
HETATM   63  H25 UNL     1       5.220  -1.660   1.456  1.00  0.00           H  
HETATM   64  H26 UNL     1       4.069  -2.573   0.531  1.00  0.00           H  
HETATM   65  H27 UNL     1       5.443  -1.999  -0.374  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   42
CONECT    5    6   11   11
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   43
CONECT   10   11   44
CONECT   11   12
CONECT   12   13   13   45
CONECT   13   14
CONECT   14   15   19   46
CONECT   15   16   16   47
CONECT   16   17   18
CONECT   17   48   49   50
CONECT   18   51   52   53
CONECT   19   20   20   26
CONECT   20   21   23
CONECT   21   22
CONECT   22   54   55   56
CONECT   23   24   24   57
CONECT   24   25   37
CONECT   25   26   26   28
CONECT   26   27
CONECT   27   58
CONECT   28   29   29   30
CONECT   30   31   31   36
CONECT   31   32   59
CONECT   32   33   33   60
CONECT   33   34   61
CONECT   34   35   36   36
CONECT   35   62
CONECT   36   37
CONECT   37   38
CONECT   38   63   64   65
END

HMDB0038599
     RDKit          3D
Acrimarine H
 65 69  0  0  0  0  0  0  0  0999 V2000
   -1.8413   -0.2210    3.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589   -0.3714    2.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3864    0.5389    1.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847    1.5840    2.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7265    2.5178    1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4002    3.5264    1.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0116    4.4167    1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6539    5.3793    1.5837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0074    4.3825   -0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3254    3.3599   -0.9601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6924    2.4394   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9824    1.3776   -0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3353    0.4353    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -0.6466   -0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831   -1.9369   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -2.7426   -0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0988   -2.4252   -2.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3968   -4.0325   -0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488   -0.5850   -0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5444   -1.7183   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707   -2.9707    0.0132 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221   -4.1558    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9373   -1.7107    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146   -0.5198   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.6319   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5085    0.6389   -0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2543    1.7344   -0.7861 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5470    1.8050   -0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    2.8870   -0.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9185    1.8262   -0.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    3.0141   -0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802    3.0678   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417    1.9171    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9887    0.6923    0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7172   -0.4471    0.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6318    0.6581    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9610   -0.5240    0.1322 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334   -1.6975    0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713   -0.4546    4.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823   -0.8759    4.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088    0.8030    4.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586    1.7150    3.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5165    5.1247   -0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2544    3.2334   -2.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651    1.3300   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -0.6150   -1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -2.2081    0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -3.0796   -2.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4984   -1.3800   -2.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1853   -2.4778   -2.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -3.8956    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2579   -4.3783   -0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5800   -4.7793   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376   -4.9763    0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1193   -4.0949    1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3390   -4.3340   -0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058   -2.6549    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0623    2.6652   -0.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0289    3.9034   -0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5070    4.0128   -0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186    1.9016    0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7130   -0.3785    0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199   -1.6603    1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691   -2.5726    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -1.9987   -0.3736 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
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 14 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 25 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 36 37  1  0
 37 38  1  0
 13  3  1  0
 26 19  1  0
 36 30  1  0
 11  5  2  0
 37 24  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  4 42  1  0
  9 43  1  0
 10 44  1  0
 12 45  1  0
 14 46  1  0
 15 47  1  0
 17 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 27 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 35 62  1  0
 38 63  1  0
 38 64  1  0
 38 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₀H₂₇NO₇

Average Molecular Weight

513.5379

Monoisotopic Molecular Weight

513.178752223

IUPAC Name

1,5-dihydroxy-3-methoxy-2-[1-(7-methoxy-2-oxo-2H-chromen-6-yl)-3-methylbut-2-en-1-yl]-10-methyl-9,10-dihydroacridin-9-one

Traditional Name

1,5-dihydroxy-3-methoxy-2-[1-(7-methoxy-2-oxochromen-6-yl)-3-methylbut-2-en-1-yl]-10-methylacridin-9-one

CAS Registry Number

132185-44-5

SMILES

COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(O)C2=C(C=C1OC)N(C)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C30H27NO7/c1-15(2)11-19(18-12-16-9-10-25(33)38-22(16)14-23(18)36-4)26-24(37-5)13-20-27(30(26)35)29(34)17-7-6-8-21(32)28(17)31(20)3/h6-14,19,32,35H,1-5H3

InChI Key

LUTVFOXEXBZKQE-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
Coumarin
Dihydroquinolone
8-hydroxyquinoline
Benzopyran
Dihydroquinoline
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Lactone
Azacycle
Oxacycle
Ether
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0032 g/L	ALOGPS
logP	4.91	ALOGPS
logP	5.81	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	145.22 m³·mol⁻¹	ChemAxon
Polarizability	54.4 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	217.448	31661259
DarkChem	[M-H]-	216.742	31661259
DeepCCS	[M+H]+	219.515	30932474
DeepCCS	[M-H]-	217.119	30932474
DeepCCS	[M-2H]-	250.002	30932474
DeepCCS	[M+Na]+	225.427	30932474
AllCCS	[M+H]+	224.0	32859911
AllCCS	[M+H-H2O]+	221.8	32859911
AllCCS	[M+NH4]+	226.0	32859911
AllCCS	[M+Na]+	226.5	32859911
AllCCS	[M-H]-	216.8	32859911
AllCCS	[M+Na-2H]-	217.4	32859911
AllCCS	[M+HCOO]-	218.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acrimarine H	COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(O)C2=C(C=C1OC)N(C)C1=C(C=CC=C1O)C2=O	5723.4	Standard polar	33892256
Acrimarine H	COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(O)C2=C(C=C1OC)N(C)C1=C(C=CC=C1O)C2=O	3592.0	Standard non polar	33892256
Acrimarine H	COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(O)C2=C(C=C1OC)N(C)C1=C(C=CC=C1O)C2=O	4741.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acrimarine H,1TMS,isomer #1	COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(OC)C=C2C(=C1O[Si](C)(C)C)C(=O)C1=CC=CC(O)=C1N2C	4479.7	Semi standard non polar	33892256
Acrimarine H,1TMS,isomer #2	COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(OC)C=C2C(=C1O)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1N2C	4454.6	Semi standard non polar	33892256
Acrimarine H,2TMS,isomer #1	COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(OC)C=C2C(=C1O[Si](C)(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1N2C	4308.2	Semi standard non polar	33892256
Acrimarine H,1TBDMS,isomer #1	COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(OC)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(O)=C1N2C	4712.7	Semi standard non polar	33892256
Acrimarine H,1TBDMS,isomer #2	COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(OC)C=C2C(=C1O)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N2C	4676.5	Semi standard non polar	33892256
Acrimarine H,2TBDMS,isomer #1	COC1=CC2=C(C=CC(=O)O2)C=C1C(C=C(C)C)C1=C(OC)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N2C	4734.1	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 - Acrimarine H GC-MS (Non-derivatized) - 70eV, Positive	splash10-001d-1011900000-e839175325a4fd90e454	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acrimarine H GC-MS (2 TMS) - 70eV, Positive	splash10-0006-1010119000-750db9a50ffd8bb17a0b	2017-10-06	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 - Acrimarine H 10V, Positive-QTOF	splash10-03di-0010490000-3a66be1eab717bb7e86c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 20V, Positive-QTOF	splash10-03di-0011940000-32f7f13a72bc045d0193	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 40V, Positive-QTOF	splash10-014l-0020900000-b4a17cb9bbf5f82d3a1d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 10V, Negative-QTOF	splash10-03di-0000290000-68ee79832474e1fb89e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 20V, Negative-QTOF	splash10-03k9-0250950000-97e8bec2c2deeba7e2e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 40V, Negative-QTOF	splash10-00us-1950800000-7edc9920f403d55d5ba6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 10V, Positive-QTOF	splash10-03di-0221090000-c916af325d0a33e4a3e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 20V, Positive-QTOF	splash10-00di-0390620000-e4f5acd77482646db875	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 40V, Positive-QTOF	splash10-00ej-0490800000-d3454c35961d01774374	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 10V, Negative-QTOF	splash10-03di-0000090000-d99c863fb45ff818592f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 20V, Negative-QTOF	splash10-03di-0236890000-e375dc0adf394053b99f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acrimarine H 40V, Negative-QTOF	splash10-03fr-0690640000-90882dc3d51b20610904	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB017990

KNApSAcK ID

C00052184

Chemspider ID

10395150

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14702537

PDB ID

Not Available

ChEBI ID

142252

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Acrimarine H (HMDB0038599)

MOL for HMDB0038599 (Acrimarine H)

3D MOL for HMDB0038599 (Acrimarine H)

3D SDF for HMDB0038599 (Acrimarine H)

3D-SDF for HMDB0038599 (Acrimarine H)

PDB for HMDB0038599 (Acrimarine H)

3D PDB for HMDB0038599 (Acrimarine H)

SMILES for HMDB0038599 (Acrimarine H)

INCHI for HMDB0038599 (Acrimarine H)

Structure for HMDB0038599 (Acrimarine H)

3D Structure for HMDB0038599 (Acrimarine H)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra