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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:01:14 UTC

Update Date

2022-03-07 02:54:01 UTC

HMDB ID

HMDB0034218

Secondary Accession Numbers

HMDB34218

Metabolite Identification

Common Name

Chrysoobtusin

Description

Chrysoobtusin belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Chrysoobtusin has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make chrysoobtusin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Chrysoobtusin.

Structure

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


  Mrv0541 05061307392D          

 26 28  0  0  0  0            999 V2000
    5.7158    0.8250    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
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    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
    2.1434    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22 16  2  0  0  0  0
 23  2  1  0  0  0  0
 23 11  1  0  0  0  0
 24  3  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25 18  1  0  0  0  0
 26  5  1  0  0  0  0
 26 19  1  0  0  0  0
M  END

HMDB0034218
     RDKit          3D
Chrysoobtusin
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.6850   -2.7404   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5379   -1.4427   -0.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -0.9070    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -1.6584   -0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8972   -1.1407   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    0.1207    0.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563    0.8264    0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7046    2.0938    1.3959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477    3.2758    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452    0.3610    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664    1.0671    1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9814    1.9336    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880    0.7099    0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975    1.8511    1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7456   -0.1054    0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -1.3767   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7357   -2.1112   -0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0035   -1.6111   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155   -2.3725   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204   -0.3489    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3648    0.2209    0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0106    0.4042    0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1328    1.6733    1.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    2.7840    0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2864   -1.9051   -0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340   -3.0496   -0.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355   -3.4198    0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7034   -3.1196   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2769   -2.7486   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2552   -2.6586   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    3.6810    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643    4.0355    1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3023    3.0137   -0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9971    2.9775    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0564    1.5911    0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803    1.8390   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061   -3.1047   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8979   -1.7122   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8057   -2.6556    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9987   -3.2378   -1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1838   -0.3146    0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1990    3.0649   -0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308    2.5350   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204    3.6816    0.6880 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
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  2  0
 10  3  1  0
 22 15  1  0
 25  5  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 21 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
M  END


  Mrv0541 05061307392D          

 26 28  0  0  0  0            999 V2000
    5.7158    0.8250    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
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    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
    2.1434    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22 16  2  0  0  0  0
 23  2  1  0  0  0  0
 23 11  1  0  0  0  0
 24  3  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25 18  1  0  0  0  0
 26  5  1  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034218

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O7/c1-8-6-9-12(18(25-4)14(8)20)16(22)13-10(15(9)21)7-11(23-2)17(24-3)19(13)26-5/h6-7,20H,1-5H3

> <INCHI_KEY>
ZMDXTRSTKHTSCE-UHFFFAOYSA-N

> <FORMULA>
C19H18O7

> <MOLECULAR_WEIGHT>
358.342

> <EXACT_MASS>
358.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
36.60717922087847

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1,6,7,8-tetramethoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.497877079666666

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.290916806815265

> <JCHEM_PKA_STRONGEST_BASIC>
-4.352133169477481

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
94.0259

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-1,6,7,8-tetramethoxy-3-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034218
     RDKit          3D
Chrysoobtusin
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.6850   -2.7404   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5379   -1.4427   -0.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -0.9070    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -1.6584   -0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8972   -1.1407   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    0.1207    0.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563    0.8264    0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7046    2.0938    1.3959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477    3.2758    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452    0.3610    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664    1.0671    1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9814    1.9336    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880    0.7099    0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975    1.8511    1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7456   -0.1054    0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -1.3767   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7357   -2.1112   -0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0035   -1.6111   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155   -2.3725   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204   -0.3489    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3648    0.2209    0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0106    0.4042    0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1328    1.6733    1.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    2.7840    0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2864   -1.9051   -0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340   -3.0496   -0.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355   -3.4198    0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7034   -3.1196   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2769   -2.7486   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2552   -2.6586   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    3.6810    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643    4.0355    1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3023    3.0137   -0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9971    2.9775    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0564    1.5911    0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803    1.8390   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061   -3.1047   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8979   -1.7122   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8057   -2.6556    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9987   -3.2378   -1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1838   -0.3146    0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1990    3.0649   -0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308    2.5350   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204    3.6816    0.6880 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
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  2  0
 10  3  1  0
 22 15  1  0
 25  5  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 21 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  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      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   26                                                            
CONECT    6    8    9                                                       
CONECT    7   10   11                                                       
CONECT    8    1    6   14                                                  
CONECT    9    6   12   15                                                  
CONECT   10    7   13   15                                                  
CONECT   11    7   17   23                                                  
CONECT   12    9   16   18                                                  
CONECT   13   10   16   19                                                  
CONECT   14    8   18   20                                                  
CONECT   15    9   10   21                                                  
CONECT   16   12   13   22                                                  
CONECT   17   11   19   24                                                  
CONECT   18   12   14   25                                                  
CONECT   19   13   17   26                                                  
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23    2   11                                                       
CONECT   24    3   17                                                       
CONECT   25    4   18                                                       
CONECT   26    5   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0034218
HETATM    1  C1  UNL     1       4.685  -2.740  -0.576  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.538  -1.443  -0.028  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.276  -0.907   0.164  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.148  -1.658  -0.188  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.897  -1.141  -0.003  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.735   0.121   0.529  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.856   0.826   0.861  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.705   2.094   1.396  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.648   3.276   0.639  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.145   0.361   0.700  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.266   1.067   1.032  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.981   1.934   0.214  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.588   0.710   0.742  1.00  0.00           C  
HETATM   14  O4  UNL     1      -0.697   1.851   1.224  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.746  -0.105   0.362  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.611  -1.377  -0.175  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.736  -2.111  -0.519  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.003  -1.611  -0.343  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.215  -2.372  -0.701  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.120  -0.349   0.191  1.00  0.00           C  
HETATM   21  O5  UNL     1      -5.365   0.221   0.398  1.00  0.00           O  
HETATM   22  C17 UNL     1      -3.011   0.404   0.543  1.00  0.00           C  
HETATM   23  O6  UNL     1      -3.133   1.673   1.079  1.00  0.00           O  
HETATM   24  C18 UNL     1      -3.161   2.784   0.208  1.00  0.00           C  
HETATM   25  C19 UNL     1      -0.286  -1.905  -0.362  1.00  0.00           C  
HETATM   26  O7  UNL     1      -0.134  -3.050  -0.844  1.00  0.00           O  
HETATM   27  H1  UNL     1       4.036  -3.420   0.036  1.00  0.00           H  
HETATM   28  H2  UNL     1       5.703  -3.120  -0.482  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.277  -2.749  -1.599  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.255  -2.659  -0.610  1.00  0.00           H  
HETATM   31  H5  UNL     1       2.698   3.681   0.591  1.00  0.00           H  
HETATM   32  H6  UNL     1       0.964   4.035   1.053  1.00  0.00           H  
HETATM   33  H7  UNL     1       1.302   3.014  -0.382  1.00  0.00           H  
HETATM   34  H8  UNL     1       4.997   2.977   0.548  1.00  0.00           H  
HETATM   35  H9  UNL     1       6.056   1.591   0.224  1.00  0.00           H  
HETATM   36  H10 UNL     1       4.680   1.839  -0.868  1.00  0.00           H  
HETATM   37  H11 UNL     1      -2.606  -3.105  -0.938  1.00  0.00           H  
HETATM   38  H12 UNL     1      -5.898  -1.712  -1.311  1.00  0.00           H  
HETATM   39  H13 UNL     1      -5.806  -2.656   0.188  1.00  0.00           H  
HETATM   40  H14 UNL     1      -4.999  -3.238  -1.358  1.00  0.00           H  
HETATM   41  H15 UNL     1      -6.184  -0.315   0.147  1.00  0.00           H  
HETATM   42  H16 UNL     1      -4.199   3.065  -0.081  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.631   2.535  -0.753  1.00  0.00           H  
HETATM   44  H18 UNL     1      -2.720   3.682   0.688  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   30
CONECT    5    6    6   25
CONECT    6    7   13
CONECT    7    8   10   10
CONECT    8    9
CONECT    9   31   32   33
CONECT   10   11
CONECT   11   12
CONECT   12   34   35   36
CONECT   13   14   14   15
CONECT   15   16   16   22
CONECT   16   17   25
CONECT   17   18   18   37
CONECT   18   19   20
CONECT   19   38   39   40
CONECT   20   21   22   22
CONECT   21   41
CONECT   22   23
CONECT   23   24
CONECT   24   42   43   44
CONECT   25   26   26
END

HMDB0034218
     RDKit          3D
Chrysoobtusin
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.6850   -2.7404   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5379   -1.4427   -0.0280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -0.9070    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -1.6584   -0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8972   -1.1407   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    0.1207    0.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563    0.8264    0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7046    2.0938    1.3959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477    3.2758    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1452    0.3610    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664    1.0671    1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9814    1.9336    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880    0.7099    0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975    1.8511    1.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7456   -0.1054    0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -1.3767   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7357   -2.1112   -0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0035   -1.6111   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2155   -2.3725   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204   -0.3489    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3648    0.2209    0.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0106    0.4042    0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1328    1.6733    1.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609    2.7840    0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2864   -1.9051   -0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340   -3.0496   -0.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355   -3.4198    0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7034   -3.1196   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2769   -2.7486   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2552   -2.6586   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975    3.6810    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643    4.0355    1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3023    3.0137   -0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9971    2.9775    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0564    1.5911    0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803    1.8390   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061   -3.1047   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8979   -1.7122   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8057   -2.6556    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9987   -3.2378   -1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1838   -0.3146    0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1990    3.0649   -0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308    2.5350   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204    3.6816    0.6880 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
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  2  0
 10  3  1  0
 22 15  1  0
 25  5  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 21 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-1,6,7,8-tetramethoxy-3-methylanthraquinone	HMDB

Chemical Formula

C₁₉H₁₈O₇

Average Molecular Weight

358.342

Monoisotopic Molecular Weight

358.10525293

IUPAC Name

2-hydroxy-1,6,7,8-tetramethoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

2-hydroxy-1,6,7,8-tetramethoxy-3-methylanthracene-9,10-dione

CAS Registry Number

70588-06-6

SMILES

COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C1

InChI Identifier

InChI=1S/C19H18O7/c1-8-6-9-12(18(25-4)14(8)20)16(22)13-10(15(9)21)7-11(23-2)17(24-3)19(13)26-5/h6-7,20H,1-5H3

InChI Key

ZMDXTRSTKHTSCE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
Anisole
Alkyl aryl ether
Ketone
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:81263 )
Anthraquinone type (C17669 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034218)
Cytoplasm (HMDB: HMDB0034218)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034218)

Source

Exogenous

Food

Food (HMDB: HMDB0034218)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Not Available

Nutrient (HMDB: HMDB0034218)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	219 - 220 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.93 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	0.028 g/L	ALOGPS
logP	2.34	ALOGPS
logP	2.5	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.29	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.03 m³·mol⁻¹	ChemAxon
Polarizability	36.61 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]+	184.288	31661259
DarkChem	[M-H]-	184.928	31661259
DeepCCS	[M+H]+	188.086	30932474
DeepCCS	[M-H]-	185.728	30932474
DeepCCS	[M-2H]-	219.407	30932474
DeepCCS	[M+Na]+	194.635	30932474
AllCCS	[M+H]+	181.9	32859911
AllCCS	[M+H-H2O]+	178.8	32859911
AllCCS	[M+NH4]+	184.7	32859911
AllCCS	[M+Na]+	185.5	32859911
AllCCS	[M-H]-	188.0	32859911
AllCCS	[M+Na-2H]-	187.8	32859911
AllCCS	[M+HCOO]-	187.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chrysoobtusin	COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C1	4505.1	Standard polar	33892256
Chrysoobtusin	COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C1	2885.4	Standard non polar	33892256
Chrysoobtusin	COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C1	2999.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chrysoobtusin,1TMS,isomer #1	COC1=CC2=C(C(=O)C3=C(C=C(C)C(O[Si](C)(C)C)=C3OC)C2=O)C(OC)=C1OC	2921.4	Semi standard non polar	33892256
Chrysoobtusin,1TBDMS,isomer #1	COC1=CC2=C(C(=O)C3=C(C=C(C)C(O[Si](C)(C)C(C)(C)C)=C3OC)C2=O)C(OC)=C1OC	3144.9	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 - Chrysoobtusin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01r7-0419000000-25a873bcf6eb15922195	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysoobtusin GC-MS (1 TMS) - 70eV, Positive	splash10-0gi3-2535900000-88686405e97d3852c6df	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysoobtusin 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 - Chrysoobtusin 10V, Positive-QTOF	splash10-0a4i-0009000000-239aeb2752a9150f3c24	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 20V, Positive-QTOF	splash10-0a4i-0009000000-87616734e0c79cefcd73	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 40V, Positive-QTOF	splash10-01ox-2198000000-788a4fa6de1a4ea15977	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 10V, Negative-QTOF	splash10-0a4i-0009000000-545e3b92340f556f8435	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 20V, Negative-QTOF	splash10-0a4l-0019000000-1781f763d9f78f31c8a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 40V, Negative-QTOF	splash10-0cdr-0192000000-b23506a06d8305deed45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 10V, Negative-QTOF	splash10-0a4i-0009000000-f52033267e0ba5a1ec2d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 20V, Negative-QTOF	splash10-0a4i-0009000000-6112580b243722d3a27b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 40V, Negative-QTOF	splash10-03di-0049000000-46c1ef05f5e59a322e45	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 10V, Positive-QTOF	splash10-0a4i-0009000000-0bfcdd2d492174763262	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 20V, Positive-QTOF	splash10-0a4i-0009000000-0f98901ffd93ad3c1fec	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoobtusin 40V, Positive-QTOF	splash10-00tu-0194000000-4ea60625d40d0e0e3a93	2021-09-25	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155381

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1841271

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 Chrysoobtusin (HMDB0034218)

MOL for HMDB0034218 (Chrysoobtusin)

3D MOL for HMDB0034218 (Chrysoobtusin)

3D SDF for HMDB0034218 (Chrysoobtusin)

3D-SDF for HMDB0034218 (Chrysoobtusin)

PDB for HMDB0034218 (Chrysoobtusin)

3D PDB for HMDB0034218 (Chrysoobtusin)

SMILES for HMDB0034218 (Chrysoobtusin)

INCHI for HMDB0034218 (Chrysoobtusin)

Structure for HMDB0034218 (Chrysoobtusin)

3D Structure for HMDB0034218 (Chrysoobtusin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra