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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:50 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029508

Secondary Accession Numbers

HMDB29508

Metabolite Identification

Common Name

Laccaic acid D

Description

Laccaic acid D, also known as flavokermesate or laccaate D, belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Laccaic acid D is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Laccaic acid D.

Structure

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

HMDB0029508
     RDKit          3D
Laccaic acid D
 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.0069   -2.4100   -0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -0.9515    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9765   -0.1515    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3032   -0.7372    0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839   -1.9537    0.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3896    0.1388    0.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563    1.2234    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183    1.9779    0.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    1.8358    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    1.0825    0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241   -0.3049    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098   -1.0383   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6058   -2.2753   -0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9340   -0.3608   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -1.1140   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9612   -2.4829   -0.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2778   -0.4687   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    0.8933   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6508    1.5135   -0.2155 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401    1.6226   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121    1.0027    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600    1.7411    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317    2.9801    0.3061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -2.4845   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1858   -2.9882   -0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5122   -2.8822    0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0058    0.2326   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9370    2.9761    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280    2.9203    0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201   -3.0212   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160   -1.0254   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0057    1.8202   -1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214    2.6894    0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 11  2  1  0
 21 14  1  0
 22 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 20 33  1  0
M  END


  Mrv0541 02241215562D          

 23 25  0  0  0  0            999 V2000
   -1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152   -0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3 16  2  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 19  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 20  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029508

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(C=C(O)C=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O7/c1-5-11-8(4-10(19)12(5)16(22)23)14(20)7-2-6(17)3-9(18)13(7)15(11)21/h2-4,17-19H,1H3,(H,22,23)

> <INCHI_KEY>
DDTNCHWMNZLWKO-UHFFFAOYSA-N

> <FORMULA>
C16H10O7

> <MOLECULAR_WEIGHT>
314.2464

> <EXACT_MASS>
314.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
29.65147765310298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,8-trihydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
3.479014407

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.430351466906881

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2260588045469785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.157683504864875

> <JCHEM_POLAR_SURFACE_AREA>
132.13000000000002

> <JCHEM_REFRACTIVITY>
79.3911

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,8-trihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029508
     RDKit          3D
Laccaic acid D
 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.0069   -2.4100   -0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -0.9515    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9765   -0.1515    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3032   -0.7372    0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839   -1.9537    0.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3896    0.1388    0.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563    1.2234    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183    1.9779    0.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    1.8358    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    1.0825    0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241   -0.3049    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098   -1.0383   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6058   -2.2753   -0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9340   -0.3608   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -1.1140   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9612   -2.4829   -0.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2778   -0.4687   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    0.8933   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6508    1.5135   -0.2155 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401    1.6226   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121    1.0027    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600    1.7411    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317    2.9801    0.3061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -2.4845   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1858   -2.9882   -0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5122   -2.8822    0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0058    0.2326   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9370    2.9761    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280    2.9203    0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201   -3.0212   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160   -1.0254   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0057    1.8202   -1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214    2.6894    0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 11  2  1  0
 21 14  1  0
 22 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 20 33  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      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.335  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.668  -1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.668  -3.080   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.668   3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.668   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.666   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.666  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.001  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.333  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.667  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.335   3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.667   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.667  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.002  -1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.001   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.001   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.333   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.002   0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.667   3.080   0.000  0.00  0.00           O+0
CONECT    1    2    7   14                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2   16                                                       
CONECT    4    2    5    9                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    1    6    8                                                  
CONECT    8    7    9   19                                                  
CONECT    9    4    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14    1   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    3   15   17                                                  
CONECT   17   16                                                            
CONECT   18   19                                                            
CONECT   19    8   18   20                                                  
CONECT   20   11   19   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0029508
HETATM    1  C1  UNL     1      -2.007  -2.410  -0.087  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.832  -0.951   0.095  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.976  -0.151   0.280  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.303  -0.737   0.354  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.484  -1.954   0.241  1.00  0.00           O  
HETATM    6  O2  UNL     1      -5.390   0.139   0.561  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.856   1.223   0.419  1.00  0.00           C  
HETATM    8  O3  UNL     1      -4.018   1.978   0.599  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.647   1.836   0.382  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.521   1.082   0.206  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.624  -0.305   0.064  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.610  -1.038  -0.107  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.606  -2.275  -0.236  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.934  -0.361  -0.134  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.062  -1.114  -0.300  1.00  0.00           C  
HETATM   16  O5  UNL     1       2.961  -2.483  -0.438  1.00  0.00           O  
HETATM   17  C12 UNL     1       4.278  -0.469  -0.323  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.404   0.893  -0.187  1.00  0.00           C  
HETATM   19  O6  UNL     1       5.651   1.514  -0.215  1.00  0.00           O  
HETATM   20  C14 UNL     1       3.240   1.623  -0.021  1.00  0.00           C  
HETATM   21  C15 UNL     1       2.012   1.003   0.005  1.00  0.00           C  
HETATM   22  C16 UNL     1       0.760   1.741   0.179  1.00  0.00           C  
HETATM   23  O7  UNL     1       0.832   2.980   0.306  1.00  0.00           O  
HETATM   24  H1  UNL     1      -2.785  -2.484  -0.928  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.186  -2.988  -0.464  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.512  -2.882   0.794  1.00  0.00           H  
HETATM   27  H4  UNL     1      -6.006   0.233  -0.240  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.937   2.976   0.700  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.628   2.920   0.497  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.820  -3.021  -0.560  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.216  -1.025  -0.453  1.00  0.00           H  
HETATM   32  H9  UNL     1       6.006   1.820  -1.128  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.321   2.689   0.086  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   11
CONECT    3    4    7
CONECT    4    5    5    6
CONECT    6   27
CONECT    7    8    9    9
CONECT    8   28
CONECT    9   10   29
CONECT   10   11   11   22
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   21
CONECT   15   16   17
CONECT   16   30
CONECT   17   18   18   31
CONECT   18   19   20
CONECT   19   32
CONECT   20   21   21   33
CONECT   21   22
CONECT   22   23   23
END

HMDB0029508
     RDKit          3D
Laccaic acid D
 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.0069   -2.4100   -0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -0.9515    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9765   -0.1515    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3032   -0.7372    0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839   -1.9537    0.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3896    0.1388    0.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563    1.2234    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183    1.9779    0.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    1.8358    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    1.0825    0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241   -0.3049    0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098   -1.0383   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6058   -2.2753   -0.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9340   -0.3608   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -1.1140   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9612   -2.4829   -0.4381 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2778   -0.4687   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    0.8933   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6508    1.5135   -0.2155 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401    1.6226   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121    1.0027    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600    1.7411    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317    2.9801    0.3061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -2.4845   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1858   -2.9882   -0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5122   -2.8822    0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0058    0.2326   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9370    2.9761    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280    2.9203    0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201   -3.0212   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160   -1.0254   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0057    1.8202   -1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214    2.6894    0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 11  2  1  0
 21 14  1  0
 22 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9,10-Dihydro-3,6,8-trihydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid	ChEBI
Flavokermesic acid	ChEBI
Xanthokermesic acid	ChEBI
9,10-Dihydro-3,6,8-trihydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylate	Generator
Flavokermesate	Generator
Xanthokermesate	Generator
Laccaate D	Generator
9,10-Dihydro-3,6,8-trihydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid, 9ci	HMDB

Chemical Formula

C₁₆H₁₀O₇

Average Molecular Weight

314.2464

Monoisotopic Molecular Weight

314.042652674

IUPAC Name

3,6,8-trihydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

3,6,8-trihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid

CAS Registry Number

18499-84-8

SMILES

CC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(C=C(O)C=C1O)C2=O

InChI Identifier

InChI=1S/C16H10O7/c1-5-11-8(4-10(19)12(5)16(22)23)14(20)7-2-6(17)3-9(18)13(7)15(11)21/h2-4,17-19H,1H3,(H,22,23)

InChI Key

DDTNCHWMNZLWKO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
Hydroxyanthraquinone
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Salicylic acid or derivatives
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029508)
Cytoplasm (HMDB: HMDB0029508)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029508)

Source

Endogenous

Endogenous (HMDB: HMDB0029508)

Plant

Plant (HMDB: HMDB0029508)

Exogenous

Food

Food (HMDB: HMDB0029508)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Not Available

Role

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	5.5 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	0.25 g/L	ALOGPS
logP	2.08	ALOGPS
logP	3.48	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.23	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.39 m³·mol⁻¹	ChemAxon
Polarizability	29.65 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]+	171.521	31661259
DarkChem	[M-H]-	171.586	31661259
DeepCCS	[M+H]+	169.212	30932474
DeepCCS	[M-H]-	166.854	30932474
DeepCCS	[M-2H]-	200.909	30932474
DeepCCS	[M+Na]+	176.136	30932474
AllCCS	[M+H]+	169.4	32859911
AllCCS	[M+H-H2O]+	166.0	32859911
AllCCS	[M+NH4]+	172.6	32859911
AllCCS	[M+Na]+	173.5	32859911
AllCCS	[M-H]-	170.1	32859911
AllCCS	[M+Na-2H]-	169.3	32859911
AllCCS	[M+HCOO]-	168.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Laccaic acid D	CC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(C=C(O)C=C1O)C2=O	4387.3	Standard polar	33892256
Laccaic acid D	CC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(C=C(O)C=C1O)C2=O	2090.2	Standard non polar	33892256
Laccaic acid D	CC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(C=C(O)C=C1O)C2=O	3103.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Laccaic acid D,1TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O	2968.2	Semi standard non polar	33892256
Laccaic acid D,1TMS,isomer #2	CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O	2922.7	Semi standard non polar	33892256
Laccaic acid D,1TMS,isomer #3	CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1C2=O	2996.9	Semi standard non polar	33892256
Laccaic acid D,1TMS,isomer #4	CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1C2=O	2911.7	Semi standard non polar	33892256
Laccaic acid D,2TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O	2918.8	Semi standard non polar	33892256
Laccaic acid D,2TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1C2=O	2905.7	Semi standard non polar	33892256
Laccaic acid D,2TMS,isomer #3	CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1C2=O	3017.5	Semi standard non polar	33892256
Laccaic acid D,2TMS,isomer #4	CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1C2=O	2877.3	Semi standard non polar	33892256
Laccaic acid D,2TMS,isomer #5	CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1C2=O	2925.8	Semi standard non polar	33892256
Laccaic acid D,2TMS,isomer #6	CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1C2=O	2933.4	Semi standard non polar	33892256
Laccaic acid D,3TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1C2=O	2906.1	Semi standard non polar	33892256
Laccaic acid D,3TMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1C2=O	2956.1	Semi standard non polar	33892256
Laccaic acid D,3TMS,isomer #3	CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1C2=O	2957.0	Semi standard non polar	33892256
Laccaic acid D,3TMS,isomer #4	CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1C2=O	2940.0	Semi standard non polar	33892256
Laccaic acid D,4TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1C2=O	2981.6	Semi standard non polar	33892256
Laccaic acid D,1TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O	3203.1	Semi standard non polar	33892256
Laccaic acid D,1TBDMS,isomer #2	CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O	3164.5	Semi standard non polar	33892256
Laccaic acid D,1TBDMS,isomer #3	CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O	3233.4	Semi standard non polar	33892256
Laccaic acid D,1TBDMS,isomer #4	CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1C2=O	3166.0	Semi standard non polar	33892256
Laccaic acid D,2TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O	3367.4	Semi standard non polar	33892256
Laccaic acid D,2TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1C2=O	3367.4	Semi standard non polar	33892256
Laccaic acid D,2TBDMS,isomer #3	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O	3444.6	Semi standard non polar	33892256
Laccaic acid D,2TBDMS,isomer #4	CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1C2=O	3363.6	Semi standard non polar	33892256
Laccaic acid D,2TBDMS,isomer #5	CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O	3417.5	Semi standard non polar	33892256
Laccaic acid D,2TBDMS,isomer #6	CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O	3429.3	Semi standard non polar	33892256
Laccaic acid D,3TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1C2=O	3529.2	Semi standard non polar	33892256
Laccaic acid D,3TBDMS,isomer #2	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O	3609.5	Semi standard non polar	33892256
Laccaic acid D,3TBDMS,isomer #3	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O	3617.0	Semi standard non polar	33892256
Laccaic acid D,3TBDMS,isomer #4	CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O	3597.4	Semi standard non polar	33892256
Laccaic acid D,4TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1C2=O	3775.7	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 - Laccaic acid D GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ds-0491000000-1358b194a0c9351ccb98	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laccaic acid D GC-MS (4 TMS) - 70eV, Positive	splash10-05tr-2202190000-65c1b7258bee80c66ba9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laccaic acid D GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laccaic acid D 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 - Laccaic acid D 10V, Positive-QTOF	splash10-014i-0049000000-ffd6441f57a0b87b0922	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 20V, Positive-QTOF	splash10-00kb-0094000000-b793451cac47f1a57676	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 40V, Positive-QTOF	splash10-0a4i-2590000000-cdace83113f5c43ec5dd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 10V, Negative-QTOF	splash10-03xr-0069000000-d71f14e1a742275501af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 20V, Negative-QTOF	splash10-014i-0091000000-c72b244aa19ca6d9de13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 40V, Negative-QTOF	splash10-016r-0290000000-fcfd0ee63ab61408da2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 10V, Negative-QTOF	splash10-03xr-0098000000-65fbab827b8177985dbf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 20V, Negative-QTOF	splash10-014i-0091000000-e73d5be536d73183f918	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 40V, Negative-QTOF	splash10-00or-0090000000-f99d06f1f8a3e9b7d4b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 10V, Positive-QTOF	splash10-00kb-0095000000-9e34f0b963f3809e8c16	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 20V, Positive-QTOF	splash10-0002-0090000000-e32a154b20754d0f2984	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laccaic acid D 40V, Positive-QTOF	splash10-004i-0290000000-75ccc2ef75c2baf21011	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

FDB000643

KNApSAcK ID

C00051186

Chemspider ID

8058979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9883304

PDB ID

Not Available

ChEBI ID

90194

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810061

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 Laccaic acid D (HMDB0029508)

MOL for HMDB0029508 (Laccaic acid D)

3D MOL for HMDB0029508 (Laccaic acid D)

3D SDF for HMDB0029508 (Laccaic acid D)

3D-SDF for HMDB0029508 (Laccaic acid D)

PDB for HMDB0029508 (Laccaic acid D)

3D PDB for HMDB0029508 (Laccaic acid D)

SMILES for HMDB0029508 (Laccaic acid D)

INCHI for HMDB0029508 (Laccaic acid D)

Structure for HMDB0029508 (Laccaic acid D)

3D Structure for HMDB0029508 (Laccaic acid D)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra