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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:55 UTC

Update Date

2022-03-07 02:53:01 UTC

HMDB ID

HMDB0031533

Secondary Accession Numbers

HMDB31533

Metabolite Identification

Common Name

Rhamnalpinogenin

Description

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

Structure

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

HMDB0031533
     RDKit          3D
Rhamnalpinogenin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.0597   -2.8584    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8280   -1.4920    0.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6358   -0.8449    0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441   -1.5240    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -0.8741   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296    0.5122    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335    1.2414    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815    2.7108    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284    0.5575    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    1.2203    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9611    0.4844    0.1961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    2.5439    0.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507    1.2134   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622    2.4504    0.0058 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    0.4873   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382    1.1640   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159    2.5064   -0.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481    0.4281   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7324   -0.9368   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9251   -1.6780   -0.3560 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5107   -1.5636   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -0.8775   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341   -1.5785   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568   -2.8468   -0.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128   -3.0654    0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2903   -3.2611   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004   -3.4261    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4085   -2.6081   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276    2.9329    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313    3.2076   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    3.2104    0.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7968    2.9275   -0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0583    3.2788   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6785    0.9665   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3904   -1.9638    0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638   -2.6445   -0.2572 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  9  3  1  0
 22 15  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 12 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 21 36  1  0
M  END


  Mrv0541 05061305592D          

 24 26  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  8  2  0  0  0  0
 14 10  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 18  7  1  0  0  0  0
 19 10  1  0  0  0  0
 20 15  2  0  0  0  0
 21 16  2  0  0  0  0
 22 17  2  0  0  0  0
 23 17  1  0  0  0  0
 24  2  1  0  0  0  0
 24 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031533

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=C(O)C=C3O)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O7/c1-6-12-9(5-11(24-2)13(6)17(22)23)15(20)8-3-7(18)4-10(19)14(8)16(12)21/h3-5,18-19H,1-2H3,(H,22,23)

> <INCHI_KEY>
QEHCRDXGPIFLOF-UHFFFAOYSA-N

> <FORMULA>
C17H12O7

> <MOLECULAR_WEIGHT>
328.273

> <EXACT_MASS>
328.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
31.709545778085193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
2.974908463

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.4309466418254475

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.164108942168368

> <JCHEM_PKA_STRONGEST_BASIC>
-4.157686154377562

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
83.87339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.12e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031533
     RDKit          3D
Rhamnalpinogenin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.0597   -2.8584    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8280   -1.4920    0.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6358   -0.8449    0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441   -1.5240    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -0.8741   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296    0.5122    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335    1.2414    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815    2.7108    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284    0.5575    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    1.2203    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9611    0.4844    0.1961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    2.5439    0.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507    1.2134   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622    2.4504    0.0058 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    0.4873   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382    1.1640   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159    2.5064   -0.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481    0.4281   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7324   -0.9368   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9251   -1.6780   -0.3560 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5107   -1.5636   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -0.8775   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341   -1.5785   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568   -2.8468   -0.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128   -3.0654    0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2903   -3.2611   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004   -3.4261    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4085   -2.6081   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276    2.9329    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313    3.2076   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    3.2104    0.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7968    2.9275   -0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0583    3.2788   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6785    0.9665   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3904   -1.9638    0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638   -2.6445   -0.2572 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  9  3  1  0
 22 15  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 12 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 21 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   24                                                            
CONECT    3    7    8                                                       
CONECT    4    7   10                                                       
CONECT    5    9   11                                                       
CONECT    6    1   12   13                                                  
CONECT    7    3    4   18                                                  
CONECT    8    3   14   15                                                  
CONECT    9    5   12   15                                                  
CONECT   10    4   14   19                                                  
CONECT   11    5   13   24                                                  
CONECT   12    6    9   16                                                  
CONECT   13    6   11   17                                                  
CONECT   14    8   10   16                                                  
CONECT   15    8    9   20                                                  
CONECT   16   12   14   21                                                  
CONECT   17   13   22   23                                                  
CONECT   18    7                                                            
CONECT   19   10                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   17                                                            
CONECT   24    2   11                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0031533
HETATM    1  C1  UNL     1      -4.060  -2.858   0.089  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.828  -1.492   0.118  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.636  -0.845   0.086  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.444  -1.524   0.015  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.231  -0.874  -0.019  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.230   0.512   0.021  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.433   1.241   0.095  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.381   2.711   0.173  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.628   0.557   0.125  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.882   1.220   0.177  1.00  0.00           C  
HETATM   11  O2  UNL     1      -4.961   0.484   0.196  1.00  0.00           O  
HETATM   12  O3  UNL     1      -4.219   2.544   0.211  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.051   1.213  -0.026  1.00  0.00           C  
HETATM   14  O4  UNL     1       1.062   2.450   0.006  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.341   0.487  -0.112  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.538   1.164  -0.155  1.00  0.00           C  
HETATM   17  O5  UNL     1       3.616   2.506  -0.121  1.00  0.00           O  
HETATM   18  C13 UNL     1       4.748   0.428  -0.237  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.732  -0.937  -0.274  1.00  0.00           C  
HETATM   20  O6  UNL     1       5.925  -1.678  -0.356  1.00  0.00           O  
HETATM   21  C15 UNL     1       3.511  -1.564  -0.229  1.00  0.00           C  
HETATM   22  C16 UNL     1       2.309  -0.877  -0.149  1.00  0.00           C  
HETATM   23  C17 UNL     1       1.034  -1.579  -0.104  1.00  0.00           C  
HETATM   24  O7  UNL     1       1.057  -2.847  -0.140  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.913  -3.065   0.802  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.290  -3.261  -0.916  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.200  -3.426   0.513  1.00  0.00           H  
HETATM   28  H4  UNL     1      -1.409  -2.608  -0.017  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.728   2.933   1.087  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.931   3.208  -0.709  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.314   3.210   0.492  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.797   2.927  -0.543  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.058   3.279  -0.071  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.679   0.967  -0.270  1.00  0.00           H  
HETATM   35  H11 UNL     1       6.390  -1.964   0.499  1.00  0.00           H  
HETATM   36  H12 UNL     1       3.464  -2.645  -0.257  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   28
CONECT    5    6    6   23
CONECT    6    7   13
CONECT    7    8    9    9
CONECT    8   29   30   31
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   32
CONECT   13   14   14   15
CONECT   15   16   16   22
CONECT   16   17   18
CONECT   17   33
CONECT   18   19   19   34
CONECT   19   20   21
CONECT   20   35
CONECT   21   22   22   36
CONECT   22   23
CONECT   23   24   24
END

HMDB0031533
     RDKit          3D
Rhamnalpinogenin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.0597   -2.8584    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8280   -1.4920    0.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6358   -0.8449    0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441   -1.5240    0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -0.8741   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296    0.5122    0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335    1.2414    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815    2.7108    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284    0.5575    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    1.2203    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9611    0.4844    0.1961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    2.5439    0.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0507    1.2134   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622    2.4504    0.0058 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    0.4873   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382    1.1640   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159    2.5064   -0.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481    0.4281   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7324   -0.9368   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9251   -1.6780   -0.3560 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5107   -1.5636   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3094   -0.8775   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341   -1.5785   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568   -2.8468   -0.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9128   -3.0654    0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2903   -3.2611   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004   -3.4261    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4085   -2.6081   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276    2.9329    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313    3.2076   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    3.2104    0.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7968    2.9275   -0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0583    3.2788   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6785    0.9665   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3904   -1.9638    0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638   -2.6445   -0.2572 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  9  3  1  0
 22 15  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 12 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 21 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,8-Dihydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid	HMDB
6,8-Dihydroxy-3-methoxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate	HMDB

Chemical Formula

C₁₇H₁₂O₇

Average Molecular Weight

328.273

Monoisotopic Molecular Weight

328.058302738

IUPAC Name

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

Traditional Name

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

CAS Registry Number

95796-47-7

SMILES

COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=C(O)C=C3O)C(=O)C2=C1

InChI Identifier

InChI=1S/C17H12O7/c1-6-12-9(5-11(24-2)13(6)17(22)23)15(20)8-3-7(18)4-10(19)14(8)16(12)21/h3-5,18-19H,1-2H3,(H,22,23)

InChI Key

QEHCRDXGPIFLOF-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 or derivatives
2-naphthalenecarboxylic acid
O-methoxybenzoic acid or derivatives
Anisole
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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: HMDB0031533)
Cytoplasm (HMDB: HMDB0031533)

Source

Endogenous

Endogenous (HMDB: HMDB0031533)

Exogenous

Food

Food (HMDB: HMDB0031533)

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	15.74 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	0.081 g/L	ALOGPS
logP	2.13	ALOGPS
logP	2.97	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.87 m³·mol⁻¹	ChemAxon
Polarizability	31.71 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]+	177.755	31661259
DarkChem	[M-H]-	174.322	31661259
DeepCCS	[M+H]+	185.05	30932474
DeepCCS	[M-H]-	182.692	30932474
DeepCCS	[M-2H]-	216.217	30932474
DeepCCS	[M+Na]+	191.445	30932474
AllCCS	[M+H]+	173.2	32859911
AllCCS	[M+H-H2O]+	169.9	32859911
AllCCS	[M+NH4]+	176.3	32859911
AllCCS	[M+Na]+	177.1	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	174.6	32859911
AllCCS	[M+HCOO]-	174.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rhamnalpinogenin	COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=C(O)C=C3O)C(=O)C2=C1	4504.9	Standard polar	33892256
Rhamnalpinogenin	COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=C(O)C=C3O)C(=O)C2=C1	2403.8	Standard non polar	33892256
Rhamnalpinogenin	COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=C(O)C=C3O)C(=O)C2=C1	3262.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rhamnalpinogenin,1TMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O)C=C(O)C=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C	2953.1	Semi standard non polar	33892256
Rhamnalpinogenin,1TMS,isomer #2	COC1=CC2=C(C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C2=O)C(C)=C1C(=O)O	2978.7	Semi standard non polar	33892256
Rhamnalpinogenin,1TMS,isomer #3	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3C2=O)C(C)=C1C(=O)O	2908.3	Semi standard non polar	33892256
Rhamnalpinogenin,2TMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C	2908.1	Semi standard non polar	33892256
Rhamnalpinogenin,2TMS,isomer #2	COC1=CC2=C(C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C	2976.7	Semi standard non polar	33892256
Rhamnalpinogenin,2TMS,isomer #3	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3C2=O)C(C)=C1C(=O)O	2952.7	Semi standard non polar	33892256
Rhamnalpinogenin,3TMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C	2957.3	Semi standard non polar	33892256
Rhamnalpinogenin,1TBDMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O)C=C(O)C=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3171.0	Semi standard non polar	33892256
Rhamnalpinogenin,1TBDMS,isomer #2	COC1=CC2=C(C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3C2=O)C(C)=C1C(=O)O	3215.6	Semi standard non polar	33892256
Rhamnalpinogenin,1TBDMS,isomer #3	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3C2=O)C(C)=C1C(=O)O	3160.7	Semi standard non polar	33892256
Rhamnalpinogenin,2TBDMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3336.1	Semi standard non polar	33892256
Rhamnalpinogenin,2TBDMS,isomer #2	COC1=CC2=C(C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3400.9	Semi standard non polar	33892256
Rhamnalpinogenin,2TBDMS,isomer #3	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3C2=O)C(C)=C1C(=O)O	3406.6	Semi standard non polar	33892256
Rhamnalpinogenin,3TBDMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3583.9	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 - Rhamnalpinogenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-0967000000-c1cb66fda64073d4d0f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnalpinogenin GC-MS (3 TMS) - 70eV, Positive	splash10-06fr-3560790000-13440f92db542a8ea03f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnalpinogenin 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 - Rhamnalpinogenin 10V, Positive-QTOF	splash10-004i-0019000000-3cc9d942131325d102bf	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 20V, Positive-QTOF	splash10-03fr-0039000000-1e5eb7720452c59264df	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 40V, Positive-QTOF	splash10-0pb9-1491000000-17f1821f33c6b885122a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 10V, Negative-QTOF	splash10-0059-0069000000-e21e7b9f54be4ca44bcd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 20V, Negative-QTOF	splash10-001i-0091000000-bc0e017b20813744c0f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 40V, Negative-QTOF	splash10-0ue9-0190000000-37101b326c3a989f5e56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 10V, Negative-QTOF	splash10-004i-0039000000-77107316314ae7f19725	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 20V, Negative-QTOF	splash10-0059-0089000000-cf3299401111918fdeb0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 40V, Negative-QTOF	splash10-0ue9-0090000000-3d3a781b1169bb1353d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 10V, Positive-QTOF	splash10-03fr-0009000000-c429850adea3680fd087	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 20V, Positive-QTOF	splash10-03di-0029000000-39e8f52d44f1ad113eb7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnalpinogenin 40V, Positive-QTOF	splash10-004l-0190000000-7253bc698d08cf30495e	2021-09-23	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

FDB008140

KNApSAcK ID

C00057696

Chemspider ID

30776906

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91476522

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1827041

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 Rhamnalpinogenin (HMDB0031533)

MOL for HMDB0031533 (Rhamnalpinogenin)

3D MOL for HMDB0031533 (Rhamnalpinogenin)

3D SDF for HMDB0031533 (Rhamnalpinogenin)

3D-SDF for HMDB0031533 (Rhamnalpinogenin)

PDB for HMDB0031533 (Rhamnalpinogenin)

3D PDB for HMDB0031533 (Rhamnalpinogenin)

SMILES for HMDB0031533 (Rhamnalpinogenin)

INCHI for HMDB0031533 (Rhamnalpinogenin)

Structure for HMDB0031533 (Rhamnalpinogenin)

3D Structure for HMDB0031533 (Rhamnalpinogenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra