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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:05:29 UTC

Update Date

2022-03-07 02:56:37 UTC

HMDB ID

HMDB0040533

Secondary Accession Numbers

HMDB40533

Metabolite Identification

Common Name

Artomunoxanthentrione epoxide

Description

Artomunoxanthentrione epoxide belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. Artomunoxanthentrione epoxide has been detected, but not quantified in, fruits. This could make artomunoxanthentrione epoxide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Artomunoxanthentrione epoxide.

Structure

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


  Mrv0541 05061311552D          

 34 39  0  0  0  0            999 V2000
    0.7651   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796   -2.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4775    1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0078    0.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4809    1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4809   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9085   -1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796   -1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664    0.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4809   -0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9085    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0519   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940   -0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796    0.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0519   -0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374   -1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230   -0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1953    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9085    0.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230    1.3622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651   -0.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651    1.3622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374    0.1247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1953    0.1247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931   -0.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 11  1  2  0  0  0  0
 11  2  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 15 12  2  0  0  0  0
 16  9  2  0  0  0  0
 17  9  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  1  0  0  0  0
 20 19  1  0  0  0  0
 21 12  1  0  0  0  0
 21 18  2  0  0  0  0
 22 18  1  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 24  7  1  0  0  0  0
 25 10  1  0  0  0  0
 25 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 17  1  0  0  0  0
 26 19  1  0  0  0  0
 26 23  1  0  0  0  0
 27 14  1  0  0  0  0
 28 17  2  0  0  0  0
 29 20  2  0  0  0  0
 30 22  2  0  0  0  0
 31  5  1  0  0  0  0
 31 16  1  0  0  0  0
 32 21  1  0  0  0  0
 32 23  1  0  0  0  0
 33 15  1  0  0  0  0
 33 24  1  0  0  0  0
 25 34  1  0  0  0  0
 26 34  1  0  0  0  0
M  END

HMDB0040533
     RDKit          3D
Artomunoxanthentrione epoxide
 56 61  0  0  0  0  0  0  0  0999 V2000
   -5.6463   -1.0838   -1.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5120   -1.7144   -1.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039   -2.7535   -2.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493   -1.3761   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -1.9915   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1588   -1.7818   -0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971   -1.6697    1.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -0.3789    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899    0.6281    1.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479    0.4689    3.1896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6007    1.9592    1.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2496    2.1816    0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7429    3.4115    0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1508    4.6436    0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4538    1.0315   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109    1.1793   -1.6227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3455   -0.3519    0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438   -0.3227    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3595   -0.0970    0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811   -0.7981    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7120   -0.1546    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254   -0.8283   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939   -2.1016   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612   -2.7496   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3567   -4.0200   -1.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409   -2.0859   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -2.6656   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367   -3.8940   -0.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0525   -0.1975   -0.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2459    1.0943    0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8036    1.9138   -0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2818    0.9984    1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0166    1.7740    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284    1.2073    0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7867   -0.3259   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5184   -1.3473   -2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074   -3.7588   -2.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -2.4903   -3.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3728   -2.8062   -3.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0119   -2.5836   -1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4552    2.8085    2.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079    5.4319   -0.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460    4.7954    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    4.7862   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681   -0.5343    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9160    0.2653   -0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5503   -2.6463   -0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6391   -4.6376   -1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3524    2.8055   -0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4773    1.2302   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9601    2.2388   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983    0.0616    2.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2439    1.8621    2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2725    0.8744    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1641    2.7939    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9334    1.7018    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 22 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
 33 34  2  0
 17  4  1  0
 26 20  1  0
 18  6  1  0
 34 21  1  0
 27  6  1  0
 17  8  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  5 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
 18 46  1  0
 23 47  1  0
 25 48  1  0
 31 49  1  0
 31 50  1  0
 31 51  1  0
 32 52  1  0
 32 53  1  0
 32 54  1  0
 33 55  1  0
 34 56  1  0
M  END


  Mrv0541 05061311552D          

 34 39  0  0  0  0            999 V2000
    0.7651   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796   -2.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4775    1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0078    0.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4809    1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4809   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9085   -1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796   -1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664    0.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4809   -0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9085    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0519   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940   -0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796    0.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0519   -0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374   -1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230   -0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1953    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230   -1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9085    0.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230    1.3622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651   -0.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651    1.3622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374    0.1247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1953    0.1247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931   -0.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 11  1  2  0  0  0  0
 11  2  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 15 12  2  0  0  0  0
 16  9  2  0  0  0  0
 17  9  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
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 20 19  1  0  0  0  0
 21 12  1  0  0  0  0
 21 18  2  0  0  0  0
 22 18  1  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 24  7  1  0  0  0  0
 25 10  1  0  0  0  0
 25 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 17  1  0  0  0  0
 26 19  1  0  0  0  0
 26 23  1  0  0  0  0
 27 14  1  0  0  0  0
 28 17  2  0  0  0  0
 29 20  2  0  0  0  0
 30 22  2  0  0  0  0
 31  5  1  0  0  0  0
 31 16  1  0  0  0  0
 32 21  1  0  0  0  0
 32 23  1  0  0  0  0
 33 15  1  0  0  0  0
 33 24  1  0  0  0  0
 25 34  1  0  0  0  0
 26 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040533

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)C23OC4(C=C(C2C1=O)C(C)=C)C3OC1=C(C(O)=CC2=C1C=CC(C)(C)O2)C4=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H22O8/c1-11(2)13-10-25-22(30)18-14(27)8-15-12(6-7-24(3,4)33-15)21(18)32-23(25)26(34-25)17(28)9-16(31-5)20(29)19(13)26/h6-10,19,23,27H,1H2,2-5H3

> <INCHI_KEY>
NDLOJOBMSNOREU-UHFFFAOYSA-N

> <FORMULA>
C26H22O8

> <MOLECULAR_WEIGHT>
462.4481

> <EXACT_MASS>
462.13146768

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
47.0456379612703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-hydroxy-20-methoxy-8,8-dimethyl-17-(prop-1-en-2-yl)-3,9,23-trioxahexacyclo[13.7.1.0¹,¹⁸.0²,¹⁵.0⁴,¹³.0⁵,¹⁰]tricosa-4(13),5(10),6,11,16,20-hexaene-14,19,22-trione

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
3.526192517666667

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.78728574833481

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.879353086663054

> <JCHEM_PKA_STRONGEST_BASIC>
-3.901266106089712

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
122.52849999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxy-20-methoxy-8,8-dimethyl-17-(prop-1-en-2-yl)-3,9,23-trioxahexacyclo[13.7.1.0¹,¹⁸.0²,¹⁵.0⁴,¹³.0⁵,¹⁰]tricosa-4(13),5(10),6,11,16,20-hexaene-14,19,22-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040533
     RDKit          3D
Artomunoxanthentrione epoxide
 56 61  0  0  0  0  0  0  0  0999 V2000
   -5.6463   -1.0838   -1.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5120   -1.7144   -1.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039   -2.7535   -2.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493   -1.3761   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -1.9915   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1588   -1.7818   -0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971   -1.6697    1.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -0.3789    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899    0.6281    1.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479    0.4689    3.1896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6007    1.9592    1.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2496    2.1816    0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7429    3.4115    0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1508    4.6436    0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4538    1.0315   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109    1.1793   -1.6227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3455   -0.3519    0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438   -0.3227    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3595   -0.0970    0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811   -0.7981    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7120   -0.1546    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254   -0.8283   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939   -2.1016   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612   -2.7496   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3567   -4.0200   -1.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409   -2.0859   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -2.6656   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367   -3.8940   -0.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0525   -0.1975   -0.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2459    1.0943    0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8036    1.9138   -0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2818    0.9984    1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0166    1.7740    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284    1.2073    0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7867   -0.3259   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5184   -1.3473   -2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074   -3.7588   -2.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -2.4903   -3.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3728   -2.8062   -3.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0119   -2.5836   -1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4552    2.8085    2.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079    5.4319   -0.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460    4.7954    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    4.7862   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681   -0.5343    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9160    0.2653   -0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5503   -2.6463   -0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6391   -4.6376   -1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3524    2.8055   -0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4773    1.2302   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9601    2.2388   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983    0.0616    2.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2439    1.8621    2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2725    0.8744    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1641    2.7939    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9334    1.7018    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 22 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
 33 34  2  0
 17  4  1  0
 26 20  1  0
 18  6  1  0
 34 21  1  0
 27  6  1  0
 17  8  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  5 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
 18 46  1  0
 23 47  1  0
 25 48  1  0
 31 49  1  0
 31 50  1  0
 31 51  1  0
 32 52  1  0
 32 53  1  0
 32 54  1  0
 33 55  1  0
 34 56  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       1.428  -2.077   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.762  -4.387   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.958   3.220   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.948   1.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.094   1.773   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.764   1.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.098   2.543   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.098  -2.077   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.095   2.543   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.429  -2.847   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.762  -2.847   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.764   0.233   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.095  -2.077   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.764  -2.847   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.098  -0.537   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.762   1.773   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.429   1.773   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.430  -2.077   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.095  -0.537   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.762   0.233   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.430  -0.537   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.096  -2.847   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.763  -0.537   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.431   1.773   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.763  -2.077   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.429   0.233   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.764  -4.387   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.763   2.543   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.428  -0.537   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.096  -4.387   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.428   2.543   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.096   0.233   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.431   0.233   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.400  -1.307   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5   31                                                            
CONECT    6    7   12                                                       
CONECT    7    6   24                                                       
CONECT    8   14   15                                                       
CONECT    9   16   17                                                       
CONECT   10   13   25                                                       
CONECT   11    1    2   13                                                  
CONECT   12    6   15   21                                                  
CONECT   13   10   11   19                                                  
CONECT   14    8   18   27                                                  
CONECT   15    8   12   33                                                  
CONECT   16    9   20   31                                                  
CONECT   17    9   26   28                                                  
CONECT   18   14   21   22                                                  
CONECT   19   13   20   26                                                  
CONECT   20   16   19   29                                                  
CONECT   21   12   18   32                                                  
CONECT   22   18   25   30                                                  
CONECT   23   25   26   32                                                  
CONECT   24    3    4    7   33                                             
CONECT   25   10   22   23   34                                             
CONECT   26   17   19   23   34                                             
CONECT   27   14                                                            
CONECT   28   17                                                            
CONECT   29   20                                                            
CONECT   30   22                                                            
CONECT   31    5   16                                                       
CONECT   32   21   23                                                       
CONECT   33   15   24                                                       
CONECT   34   25   26                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

COMPND    HMDB0040533
HETATM    1  C1  UNL     1      -5.646  -1.084  -1.437  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.512  -1.714  -1.673  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.404  -2.754  -2.716  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.349  -1.376  -0.895  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.168  -1.992  -1.090  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.159  -1.782  -0.045  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.697  -1.670   1.245  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.036  -0.379   0.929  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.090   0.628   1.998  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.748   0.469   3.190  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.601   1.959   1.619  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.250   2.182   0.485  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.743   3.411   0.094  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.151   4.644   0.376  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.454   1.032  -0.412  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.711   1.179  -1.623  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.346  -0.352   0.162  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.844  -0.323   0.032  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.360  -0.097   0.789  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.481  -0.798   0.329  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.712  -0.155   0.377  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.825  -0.828  -0.071  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.694  -2.102  -0.548  1.00  0.00           C  
HETATM   24  C19 UNL     1       2.461  -2.750  -0.597  1.00  0.00           C  
HETATM   25  O6  UNL     1       2.357  -4.020  -1.079  1.00  0.00           O  
HETATM   26  C20 UNL     1       1.341  -2.086  -0.151  1.00  0.00           C  
HETATM   27  C21 UNL     1       0.004  -2.666  -0.152  1.00  0.00           C  
HETATM   28  O7  UNL     1      -0.137  -3.894  -0.242  1.00  0.00           O  
HETATM   29  O8  UNL     1       5.052  -0.198  -0.028  1.00  0.00           O  
HETATM   30  C22 UNL     1       5.246   1.094   0.456  1.00  0.00           C  
HETATM   31  C23 UNL     1       5.804   1.914  -0.712  1.00  0.00           C  
HETATM   32  C24 UNL     1       6.282   0.998   1.565  1.00  0.00           C  
HETATM   33  C25 UNL     1       4.017   1.774   0.925  1.00  0.00           C  
HETATM   34  C26 UNL     1       2.828   1.207   0.895  1.00  0.00           C  
HETATM   35  H1  UNL     1      -5.787  -0.326  -0.698  1.00  0.00           H  
HETATM   36  H2  UNL     1      -6.518  -1.347  -2.037  1.00  0.00           H  
HETATM   37  H3  UNL     1      -4.207  -3.759  -2.300  1.00  0.00           H  
HETATM   38  H4  UNL     1      -3.566  -2.490  -3.392  1.00  0.00           H  
HETATM   39  H5  UNL     1      -5.373  -2.806  -3.251  1.00  0.00           H  
HETATM   40  H6  UNL     1      -2.012  -2.584  -1.958  1.00  0.00           H  
HETATM   41  H7  UNL     1      -2.455   2.808   2.271  1.00  0.00           H  
HETATM   42  H8  UNL     1      -3.808   5.432  -0.086  1.00  0.00           H  
HETATM   43  H9  UNL     1      -3.146   4.795   1.464  1.00  0.00           H  
HETATM   44  H10 UNL     1      -2.156   4.786  -0.096  1.00  0.00           H  
HETATM   45  H11 UNL     1      -4.168  -0.534   0.865  1.00  0.00           H  
HETATM   46  H12 UNL     1      -0.916   0.265  -0.883  1.00  0.00           H  
HETATM   47  H13 UNL     1       4.550  -2.646  -0.903  1.00  0.00           H  
HETATM   48  H14 UNL     1       1.639  -4.638  -1.211  1.00  0.00           H  
HETATM   49  H15 UNL     1       6.352   2.805  -0.355  1.00  0.00           H  
HETATM   50  H16 UNL     1       6.477   1.230  -1.284  1.00  0.00           H  
HETATM   51  H17 UNL     1       4.960   2.239  -1.353  1.00  0.00           H  
HETATM   52  H18 UNL     1       6.098   0.062   2.132  1.00  0.00           H  
HETATM   53  H19 UNL     1       6.244   1.862   2.252  1.00  0.00           H  
HETATM   54  H20 UNL     1       7.273   0.874   1.082  1.00  0.00           H  
HETATM   55  H21 UNL     1       4.164   2.794   1.304  1.00  0.00           H  
HETATM   56  H22 UNL     1       1.933   1.702   1.237  1.00  0.00           H  
CONECT    1    2    2   35   36
CONECT    2    3    4
CONECT    3   37   38   39
CONECT    4    5    5   17
CONECT    5    6   40
CONECT    6    7   18   27
CONECT    7    8
CONECT    8    9   17   18
CONECT    9   10   10   11
CONECT   11   12   12   41
CONECT   12   13   15
CONECT   13   14
CONECT   14   42   43   44
CONECT   15   16   16   17
CONECT   17   45
CONECT   18   19   46
CONECT   19   20
CONECT   20   21   21   26
CONECT   21   22   34
CONECT   22   23   23   29
CONECT   23   24   47
CONECT   24   25   26   26
CONECT   25   48
CONECT   26   27
CONECT   27   28   28
CONECT   29   30
CONECT   30   31   32   33
CONECT   31   49   50   51
CONECT   32   52   53   54
CONECT   33   34   34   55
CONECT   34   56
END

HMDB0040533
     RDKit          3D
Artomunoxanthentrione epoxide
 56 61  0  0  0  0  0  0  0  0999 V2000
   -5.6463   -1.0838   -1.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5120   -1.7144   -1.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039   -2.7535   -2.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493   -1.3761   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -1.9915   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1588   -1.7818   -0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6971   -1.6697    1.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -0.3789    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899    0.6281    1.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479    0.4689    3.1896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6007    1.9592    1.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2496    2.1816    0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7429    3.4115    0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1508    4.6436    0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4538    1.0315   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109    1.1793   -1.6227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3455   -0.3519    0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438   -0.3227    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3595   -0.0970    0.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811   -0.7981    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7120   -0.1546    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254   -0.8283   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939   -2.1016   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612   -2.7496   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3567   -4.0200   -1.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3409   -2.0859   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -2.6656   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367   -3.8940   -0.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0525   -0.1975   -0.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2459    1.0943    0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8036    1.9138   -0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2818    0.9984    1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0166    1.7740    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284    1.2073    0.8954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7867   -0.3259   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5184   -1.3473   -2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074   -3.7588   -2.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -2.4903   -3.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3728   -2.8062   -3.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0119   -2.5836   -1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4552    2.8085    2.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079    5.4319   -0.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460    4.7954    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    4.7862   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681   -0.5343    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9160    0.2653   -0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5503   -2.6463   -0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6391   -4.6376   -1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3524    2.8055   -0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4773    1.2302   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9601    2.2388   -1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0983    0.0616    2.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2439    1.8621    2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2725    0.8744    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1641    2.7939    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9334    1.7018    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 22 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
 33 34  2  0
 17  4  1  0
 26 20  1  0
 18  6  1  0
 34 21  1  0
 27  6  1  0
 17  8  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  5 40  1  0
 11 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
 18 46  1  0
 23 47  1  0
 25 48  1  0
 31 49  1  0
 31 50  1  0
 31 51  1  0
 32 52  1  0
 32 53  1  0
 32 54  1  0
 33 55  1  0
 34 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₆H₂₂O₈

Average Molecular Weight

462.4481

Monoisotopic Molecular Weight

462.13146768

IUPAC Name

12-hydroxy-20-methoxy-8,8-dimethyl-17-(prop-1-en-2-yl)-3,9,23-trioxahexacyclo[13.7.1.0¹,¹⁸.0²,¹⁵.0⁴,¹³.0⁵,¹⁰]tricosa-4(13),5(10),6,11,16,20-hexaene-14,19,22-trione

Traditional Name

12-hydroxy-20-methoxy-8,8-dimethyl-17-(prop-1-en-2-yl)-3,9,23-trioxahexacyclo[13.7.1.0¹,¹⁸.0²,¹⁵.0⁴,¹³.0⁵,¹⁰]tricosa-4(13),5(10),6,11,16,20-hexaene-14,19,22-trione

CAS Registry Number

143522-33-2

SMILES

COC1=CC(=O)C23OC4(C=C(C2C1=O)C(C)=C)C3OC1=C(C(O)=CC2=C1C=CC(C)(C)O2)C4=O

InChI Identifier

InChI=1S/C26H22O8/c1-11(2)13-10-25-22(30)18-14(27)8-15-12(6-7-24(3,4)33-15)21(18)32-23(25)26(34-25)17(28)9-16(31-5)20(29)19(13)26/h6-10,19,23,27H,1H2,2-5H3

InChI Key

NDLOJOBMSNOREU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Naphthopyran
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Naphthalene
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Cyclohexenone
Pyran
Benzenoid
Vinylogous ester
Vinylogous acid
Oxetane
Ketone
Oxacycle
Ether
Dialkyl ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040533)
Cell membrane (HMDB: HMDB0040533)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040533)

Source

Exogenous

Exogenous (HMDB: HMDB0040533)

Food

Food (HMDB: HMDB0040533)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040533)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040533)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	248 - 251 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	3.39	ALOGPS
logP	3.53	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.88	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	122.53 m³·mol⁻¹	ChemAxon
Polarizability	47.05 Å³	ChemAxon
Number of Rings	6	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
DeepCCS	[M-2H]-	234.701	30932474
DeepCCS	[M+Na]+	209.948	30932474
AllCCS	[M+H]+	208.7	32859911
AllCCS	[M+H-H2O]+	206.4	32859911
AllCCS	[M+NH4]+	210.8	32859911
AllCCS	[M+Na]+	211.4	32859911
AllCCS	[M-H]-	214.9	32859911
AllCCS	[M+Na-2H]-	215.5	32859911
AllCCS	[M+HCOO]-	216.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.54 minutes	32390414
Predicted by Siyang on May 30, 2022	15.4967 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.21 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3304.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	259.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	710.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	806.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1389.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	546.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1602.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	490.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	438.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	256.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	220.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artomunoxanthentrione epoxide	COC1=CC(=O)C23OC4(C=C(C2C1=O)C(C)=C)C3OC1=C(C(O)=CC2=C1C=CC(C)(C)O2)C4=O	4937.8	Standard polar	33892256
Artomunoxanthentrione epoxide	COC1=CC(=O)C23OC4(C=C(C2C1=O)C(C)=C)C3OC1=C(C(O)=CC2=C1C=CC(C)(C)O2)C4=O	3446.1	Standard non polar	33892256
Artomunoxanthentrione epoxide	COC1=CC(=O)C23OC4(C=C(C2C1=O)C(C)=C)C3OC1=C(C(O)=CC2=C1C=CC(C)(C)O2)C4=O	3482.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artomunoxanthentrione epoxide,1TMS,isomer #1	C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(=O)C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C)=C1C3=O	3535.0	Semi standard non polar	33892256
Artomunoxanthentrione epoxide,1TMS,isomer #2	C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O)=C1C3=O	3411.5	Semi standard non polar	33892256
Artomunoxanthentrione epoxide,2TMS,isomer #1	C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C)=C1C3=O	3367.0	Semi standard non polar	33892256
Artomunoxanthentrione epoxide,2TMS,isomer #1	C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C)=C1C3=O	3463.7	Standard non polar	33892256
Artomunoxanthentrione epoxide,1TBDMS,isomer #1	C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(=O)C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C1C3=O	3763.8	Semi standard non polar	33892256
Artomunoxanthentrione epoxide,1TBDMS,isomer #2	C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O)=C1C3=O	3644.2	Semi standard non polar	33892256
Artomunoxanthentrione epoxide,2TBDMS,isomer #1	C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C1C3=O	3785.1	Semi standard non polar	33892256
Artomunoxanthentrione epoxide,2TBDMS,isomer #1	C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C1C3=O	3858.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Artomunoxanthentrione epoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01qd-7301900000-165ae9f61b9b20029be3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artomunoxanthentrione epoxide GC-MS (1 TMS) - 70eV, Positive	splash10-0aor-9330260000-21f600558731b5655e7d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artomunoxanthentrione epoxide 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 - Artomunoxanthentrione epoxide 10V, Positive-QTOF	splash10-03di-0000900000-135522ccc3af3d788697	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 20V, Positive-QTOF	splash10-0301-2061900000-16ccd0301666c1e7a6f2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 40V, Positive-QTOF	splash10-016r-5940000000-8df62234e783b8adbbf5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 10V, Negative-QTOF	splash10-03di-0010900000-aff4b3d70741e2832fbb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 20V, Negative-QTOF	splash10-03di-1011900000-f2ea2049b93995a8bf8a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 40V, Negative-QTOF	splash10-0aru-6982000000-8a748a350724c38b44cf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 10V, Positive-QTOF	splash10-03di-0000900000-9208e3ee3180b8cb41df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 20V, Positive-QTOF	splash10-03di-0000900000-4df73206b8b8faa7de44	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 40V, Positive-QTOF	splash10-03k9-1001900000-cbea8bae195f2e91da52	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 10V, Negative-QTOF	splash10-03di-0000900000-9a0269f6702280e74668	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 20V, Negative-QTOF	splash10-03di-0000900000-9e56d292e999e4a8eb14	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 40V, Negative-QTOF	splash10-014i-1012900000-0e2dbe2dc18ec4f37098	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020301

KNApSAcK ID

Not Available

Chemspider ID

35014957

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752846

PDB ID

Not Available

ChEBI ID

192294

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1884141

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 Artomunoxanthentrione epoxide (HMDB0040533)

MOL for HMDB0040533 (Artomunoxanthentrione epoxide)

3D MOL for HMDB0040533 (Artomunoxanthentrione epoxide)

3D SDF for HMDB0040533 (Artomunoxanthentrione epoxide)

3D-SDF for HMDB0040533 (Artomunoxanthentrione epoxide)

PDB for HMDB0040533 (Artomunoxanthentrione epoxide)

3D PDB for HMDB0040533 (Artomunoxanthentrione epoxide)

SMILES for HMDB0040533 (Artomunoxanthentrione epoxide)

INCHI for HMDB0040533 (Artomunoxanthentrione epoxide)

Structure for HMDB0040533 (Artomunoxanthentrione epoxide)

3D Structure for HMDB0040533 (Artomunoxanthentrione epoxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra