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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:47:45 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034021

Secondary Accession Numbers

HMDB34021

Metabolite Identification

Common Name

Artobiloxanthone

Description

Artobiloxanthone 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. Artobiloxanthone has been detected, but not quantified in, breadfruits (Artocarpus altilis) and fruits. This could make artobiloxanthone a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Artobiloxanthone.

Structure

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


  Mrv0541 05061307302D          

 32 36  0  0  0  0            999 V2000
   -2.8579    0.0000    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
    3.8545    2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848    1.9192    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
    2.8579    2.4750    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
   -1.4289    2.4750    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
   -2.1434   -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
   -1.4289    0.0000    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    2.0625    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
   -2.1434    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
   -1.4289    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
    1.4289    0.0000    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    1.2375    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
    0.0000    0.8250    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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  2  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 14  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22 16  2  0  0  0  0
 22 18  1  0  0  0  0
 23 11  1  0  0  0  0
 23 20  2  0  0  0  0
 24 13  2  0  0  0  0
 24 19  1  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25  6  1  0  0  0  0
 26 14  1  0  0  0  0
 27 15  1  0  0  0  0
 28 16  1  0  0  0  0
 29 21  2  0  0  0  0
 30 22  1  0  0  0  0
 31 23  1  0  0  0  0
 31 24  1  0  0  0  0
 32 17  1  0  0  0  0
 32 25  1  0  0  0  0
M  END

HMDB0034021
     RDKit          3D
Artobiloxanthone
 54 58  0  0  0  0  0  0  0  0999 V2000
   -5.5773   -1.3147   -0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9465   -0.1727   -0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7256    1.0881   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5061   -0.1641   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -1.2742   -1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -0.8978   -1.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287   -0.1619   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503    0.0586    0.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677   -0.4300   -0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -0.1827   -0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6248   -0.6648   -1.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588   -1.4030   -2.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -1.6853   -2.9158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -2.4240   -3.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280   -1.1804   -1.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -1.4103   -2.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200   -2.0714   -2.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9867   -0.3898   -1.5623 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484    0.3570   -0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2676    1.5840   -1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6452   -0.4622    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5736    0.8561    0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616    0.6032    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6452    0.3922    0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269    0.9187    2.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431    1.1149    2.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9567    1.2332    3.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054    1.0219    3.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1897    1.3216    4.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8481    0.5017    1.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2124    0.2924    1.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095    0.1934    0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0834   -2.2800   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6502   -1.3341   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1430    1.9440   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7287    1.0163   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9286    1.4214   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906    0.7674   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266   -1.5121   -2.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255   -2.2096   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8315   -1.7846   -3.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400   -2.7159   -4.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5503    2.3125   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9070    2.0042   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9612    1.2731   -1.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0144   -1.2761   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4786    0.1868    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1613   -0.8809    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9198    1.4434    1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6266    1.0156    1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155    1.4915    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256    1.6411    4.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7873    1.7019    5.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7828    0.5266    2.6545 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  2  0
  7 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 32  4  1  0
 16  6  1  0
 32 24  1  0
 15  9  1  0
 23 10  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
 12 41  1  0
 14 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 31 54  1  0
M  END


  Mrv0541 05061307302D          

 32 36  0  0  0  0            999 V2000
   -2.8579    0.0000    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
    3.8545    2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848    1.9192    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
    2.8579    2.4750    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
   -1.4289    2.4750    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
   -2.1434   -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
   -1.4289    0.0000    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    2.0625    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
   -2.1434    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
   -1.4289    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
    1.4289    0.0000    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    1.2375    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
    0.0000    0.8250    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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  2  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 14  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22 16  2  0  0  0  0
 22 18  1  0  0  0  0
 23 11  1  0  0  0  0
 23 20  2  0  0  0  0
 24 13  2  0  0  0  0
 24 19  1  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25  6  1  0  0  0  0
 26 14  1  0  0  0  0
 27 15  1  0  0  0  0
 28 16  1  0  0  0  0
 29 21  2  0  0  0  0
 30 22  1  0  0  0  0
 31 23  1  0  0  0  0
 31 24  1  0  0  0  0
 32 17  1  0  0  0  0
 32 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034021

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O7/c1-10(2)12-7-13-21(29)20-15(27)9-17-11(5-6-25(3,4)32-17)23(20)31-24(13)19-14(26)8-16(28)22(30)18(12)19/h5-6,8-9,12,26-28,30H,1,7H2,2-4H3

> <INCHI_KEY>
ZIYAGIMFLYOZDS-UHFFFAOYSA-N

> <FORMULA>
C25H22O7

> <MOLECULAR_WEIGHT>
434.438

> <EXACT_MASS>
434.136553058

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
45.43099323466929

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11,18,19,21-tetrahydroxy-7,7-dimethyl-16-(prop-1-en-2-yl)-2,8-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one

> <ALOGPS_LOGP>
4.31

> <JCHEM_LOGP>
4.419954236666667

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.892409609040453

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.26366809858807

> <JCHEM_PKA_STRONGEST_BASIC>
-4.812599756636185

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
120.35999999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11,18,19,21-tetrahydroxy-7,7-dimethyl-16-(prop-1-en-2-yl)-2,8-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034021
     RDKit          3D
Artobiloxanthone
 54 58  0  0  0  0  0  0  0  0999 V2000
   -5.5773   -1.3147   -0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9465   -0.1727   -0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7256    1.0881   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5061   -0.1641   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -1.2742   -1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -0.8978   -1.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287   -0.1619   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503    0.0586    0.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677   -0.4300   -0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -0.1827   -0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6248   -0.6648   -1.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588   -1.4030   -2.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -1.6853   -2.9158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -2.4240   -3.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280   -1.1804   -1.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -1.4103   -2.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200   -2.0714   -2.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9867   -0.3898   -1.5623 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484    0.3570   -0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2676    1.5840   -1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6452   -0.4622    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5736    0.8561    0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616    0.6032    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6452    0.3922    0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269    0.9187    2.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431    1.1149    2.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9567    1.2332    3.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054    1.0219    3.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1897    1.3216    4.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8481    0.5017    1.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2124    0.2924    1.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095    0.1934    0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0834   -2.2800   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6502   -1.3341   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1430    1.9440   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7287    1.0163   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9286    1.4214   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906    0.7674   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266   -1.5121   -2.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255   -2.2096   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8315   -1.7846   -3.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400   -2.7159   -4.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5503    2.3125   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9070    2.0042   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9612    1.2731   -1.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0144   -1.2761   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4786    0.1868    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1613   -0.8809    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9198    1.4434    1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6266    1.0156    1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155    1.4915    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256    1.6411    4.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7873    1.7019    5.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7828    0.5266    2.6545 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  2  0
  7 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 32  4  1  0
 16  6  1  0
 32 24  1  0
 15  9  1  0
 23 10  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
 12 41  1  0
 14 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 31 54  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   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.195   5.297   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.185   3.583   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   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      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    6   11                                                       
CONECT    6    5   25                                                       
CONECT    7   12   13                                                       
CONECT    8   14   16                                                       
CONECT    9   15   17                                                       
CONECT   10    1    2   12                                                  
CONECT   11    5   17   23                                                  
CONECT   12    7   10   18                                                  
CONECT   13    7   21   24                                                  
CONECT   14    8   19   26                                                  
CONECT   15    9   20   27                                                  
CONECT   16    8   22   28                                                  
CONECT   17    9   11   32                                                  
CONECT   18   12   19   22                                                  
CONECT   19   14   18   24                                                  
CONECT   20   15   21   23                                                  
CONECT   21   13   20   29                                                  
CONECT   22   16   18   30                                                  
CONECT   23   11   20   31                                                  
CONECT   24   13   19   31                                                  
CONECT   25    3    4    6   32                                             
CONECT   26   14                                                            
CONECT   27   15                                                            
CONECT   28   16                                                            
CONECT   29   21                                                            
CONECT   30   22                                                            
CONECT   31   23   24                                                       
CONECT   32   17   25                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

COMPND    HMDB0034021
HETATM    1  C1  UNL     1      -5.577  -1.315  -0.885  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.947  -0.173  -0.675  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.726   1.088  -0.674  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.506  -0.164  -0.449  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.730  -1.274  -1.058  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.282  -0.898  -1.040  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.729  -0.162  -0.018  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.550   0.059   0.059  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.368  -0.430  -0.871  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.735  -0.183  -0.771  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.625  -0.665  -1.707  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.159  -1.403  -2.759  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.804  -1.685  -2.916  1.00  0.00           C  
HETATM   14  O2  UNL     1       1.405  -2.424  -3.982  1.00  0.00           O  
HETATM   15  C13 UNL     1       0.928  -1.180  -1.947  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.424  -1.410  -2.020  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.920  -2.071  -2.946  1.00  0.00           O  
HETATM   18  O4  UNL     1       4.987  -0.390  -1.562  1.00  0.00           O  
HETATM   19  C15 UNL     1       5.548   0.357  -0.532  1.00  0.00           C  
HETATM   20  C16 UNL     1       6.268   1.584  -1.106  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.645  -0.462   0.153  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.574   0.856   0.447  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.262   0.603   0.334  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.645   0.392   0.992  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.127   0.919   2.180  1.00  0.00           C  
HETATM   26  O5  UNL     1       0.243   1.115   2.258  1.00  0.00           O  
HETATM   27  C22 UNL     1      -1.957   1.233   3.244  1.00  0.00           C  
HETATM   28  C23 UNL     1      -3.305   1.022   3.124  1.00  0.00           C  
HETATM   29  O6  UNL     1      -4.190   1.322   4.179  1.00  0.00           O  
HETATM   30  C24 UNL     1      -3.848   0.502   1.950  1.00  0.00           C  
HETATM   31  O7  UNL     1      -5.212   0.292   1.857  1.00  0.00           O  
HETATM   32  C25 UNL     1      -3.009   0.193   0.883  1.00  0.00           C  
HETATM   33  H1  UNL     1      -5.083  -2.280  -0.902  1.00  0.00           H  
HETATM   34  H2  UNL     1      -6.650  -1.334  -1.055  1.00  0.00           H  
HETATM   35  H3  UNL     1      -5.143   1.944  -0.267  1.00  0.00           H  
HETATM   36  H4  UNL     1      -6.729   1.016  -0.241  1.00  0.00           H  
HETATM   37  H5  UNL     1      -5.929   1.421  -1.750  1.00  0.00           H  
HETATM   38  H6  UNL     1      -3.091   0.767  -1.084  1.00  0.00           H  
HETATM   39  H7  UNL     1      -3.027  -1.512  -2.100  1.00  0.00           H  
HETATM   40  H8  UNL     1      -2.825  -2.210  -0.442  1.00  0.00           H  
HETATM   41  H9  UNL     1       3.831  -1.785  -3.492  1.00  0.00           H  
HETATM   42  H10 UNL     1       0.540  -2.716  -4.257  1.00  0.00           H  
HETATM   43  H11 UNL     1       5.550   2.312  -1.507  1.00  0.00           H  
HETATM   44  H12 UNL     1       6.907   2.004  -0.301  1.00  0.00           H  
HETATM   45  H13 UNL     1       6.961   1.273  -1.918  1.00  0.00           H  
HETATM   46  H14 UNL     1       7.014  -1.276  -0.495  1.00  0.00           H  
HETATM   47  H15 UNL     1       7.479   0.187   0.456  1.00  0.00           H  
HETATM   48  H16 UNL     1       6.161  -0.881   1.070  1.00  0.00           H  
HETATM   49  H17 UNL     1       4.920   1.443   1.283  1.00  0.00           H  
HETATM   50  H18 UNL     1       2.627   1.016   1.103  1.00  0.00           H  
HETATM   51  H19 UNL     1       0.615   1.491   3.107  1.00  0.00           H  
HETATM   52  H20 UNL     1      -1.526   1.641   4.154  1.00  0.00           H  
HETATM   53  H21 UNL     1      -3.787   1.702   5.035  1.00  0.00           H  
HETATM   54  H22 UNL     1      -5.783   0.527   2.654  1.00  0.00           H  
CONECT    1    2    2   33   34
CONECT    2    3    4
CONECT    3   35   36   37
CONECT    4    5   32   38
CONECT    5    6   39   40
CONECT    6    7    7   16
CONECT    7    8   24
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   23
CONECT   11   12   12   18
CONECT   12   13   41
CONECT   13   14   15   15
CONECT   14   42
CONECT   15   16
CONECT   16   17   17
CONECT   18   19
CONECT   19   20   21   22
CONECT   20   43   44   45
CONECT   21   46   47   48
CONECT   22   23   23   49
CONECT   23   50
CONECT   24   25   25   32
CONECT   25   26   27
CONECT   26   51
CONECT   27   28   28   52
CONECT   28   29   30
CONECT   29   53
CONECT   30   31   32   32
CONECT   31   54
END

HMDB0034021
     RDKit          3D
Artobiloxanthone
 54 58  0  0  0  0  0  0  0  0999 V2000
   -5.5773   -1.3147   -0.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9465   -0.1727   -0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7256    1.0881   -0.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5061   -0.1641   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -1.2742   -1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -0.8978   -1.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287   -0.1619   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503    0.0586    0.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677   -0.4300   -0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -0.1827   -0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6248   -0.6648   -1.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1588   -1.4030   -2.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -1.6853   -2.9158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055   -2.4240   -3.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280   -1.1804   -1.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -1.4103   -2.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200   -2.0714   -2.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9867   -0.3898   -1.5623 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484    0.3570   -0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2676    1.5840   -1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6452   -0.4622    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5736    0.8561    0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616    0.6032    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6452    0.3922    0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269    0.9187    2.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431    1.1149    2.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9567    1.2332    3.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054    1.0219    3.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1897    1.3216    4.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8481    0.5017    1.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2124    0.2924    1.8566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095    0.1934    0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0834   -2.2800   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6502   -1.3341   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1430    1.9440   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7287    1.0163   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9286    1.4214   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906    0.7674   -1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266   -1.5121   -2.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255   -2.2096   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8315   -1.7846   -3.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400   -2.7159   -4.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5503    2.3125   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9070    2.0042   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9612    1.2731   -1.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0144   -1.2761   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4786    0.1868    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1613   -0.8809    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9198    1.4434    1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6266    1.0156    1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155    1.4915    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256    1.6411    4.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7873    1.7019    5.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7828    0.5266    2.6545 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  2  0
  7 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 32  4  1  0
 16  6  1  0
 32 24  1  0
 15  9  1  0
 23 10  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
 12 41  1  0
 14 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 31 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8,9-dihydro-6,10,11,13-Tetrahydroxy-3,3-dimethyl-9-(1-methylethenyl)-3H,7H-benzo[c]pyrano[3,2-H]xanthen-7-one, 9ci	HMDB
KB 1	HMDB
Artobiloxanthone	MeSH

Chemical Formula

C₂₅H₂₂O₇

Average Molecular Weight

434.438

Monoisotopic Molecular Weight

434.136553058

IUPAC Name

11,18,19,21-tetrahydroxy-7,7-dimethyl-16-(prop-1-en-2-yl)-2,8-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one

Traditional Name

11,18,19,21-tetrahydroxy-7,7-dimethyl-16-(prop-1-en-2-yl)-2,8-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one

CAS Registry Number

121748-25-2

SMILES

CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C(O)C=C2O

InChI Identifier

InChI=1S/C25H22O7/c1-10(2)12-7-13-21(29)20-15(27)9-17-11(5-6-25(3,4)32-17)23(20)31-24(13)19-14(26)8-16(28)22(30)18(12)19/h5-6,8-9,12,26-28,30H,1,7H2,2-4H3

InChI Key

ZIYAGIMFLYOZDS-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
Naphthopyranone
Naphthopyran
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-naphthol
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Polyol
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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: HMDB0034021)
Cell membrane (HMDB: HMDB0034021)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034021)

Source

Exogenous

Exogenous (HMDB: HMDB0034021)

Food

Food (HMDB: HMDB0034021)

Fruit

Tropical fruit

Breadfruit (FooDB: FOOD00309)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034021)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034021)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	162 - 164 °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	0.028 g/L	ALOGPS
logP	4.31	ALOGPS
logP	4.42	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.26	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	120.36 m³·mol⁻¹	ChemAxon
Polarizability	45.43 Å³	ChemAxon
Number of Rings	5	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]+	200.359	31661259
DarkChem	[M-H]-	197.271	31661259
DeepCCS	[M+H]+	200.919	30932474
DeepCCS	[M-H]-	198.523	30932474
DeepCCS	[M-2H]-	231.407	30932474
DeepCCS	[M+Na]+	207.121	30932474
AllCCS	[M+H]+	204.0	32859911
AllCCS	[M+H-H2O]+	201.4	32859911
AllCCS	[M+NH4]+	206.4	32859911
AllCCS	[M+Na]+	207.1	32859911
AllCCS	[M-H]-	204.7	32859911
AllCCS	[M+Na-2H]-	204.5	32859911
AllCCS	[M+HCOO]-	204.5	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.	7.54 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6521 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2828.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	240.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	194.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	147.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	803.7 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	809.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	123.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1253.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	559.5 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	1620.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	461.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	455.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	266.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	208.3 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	10.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artobiloxanthone	CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C(O)C=C2O	5291.4	Standard polar	33892256
Artobiloxanthone	CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C(O)C=C2O	3862.8	Standard non polar	33892256
Artobiloxanthone	CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C(O)C=C2O	4026.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artobiloxanthone,1TMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C=C(O)C(O)=C21	3745.6	Semi standard non polar	33892256
Artobiloxanthone,1TMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O)C(O[Si](C)(C)C)=C21	3734.6	Semi standard non polar	33892256
Artobiloxanthone,1TMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C)C(O)=C21	3778.0	Semi standard non polar	33892256
Artobiloxanthone,1TMS,isomer #4	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O)C(O)=C21	3762.8	Semi standard non polar	33892256
Artobiloxanthone,2TMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O)C(O)=C21	3659.7	Semi standard non polar	33892256
Artobiloxanthone,2TMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C)C(O)=C21	3687.2	Semi standard non polar	33892256
Artobiloxanthone,2TMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C=C(O)C(O[Si](C)(C)C)=C21	3627.4	Semi standard non polar	33892256
Artobiloxanthone,2TMS,isomer #4	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O)C(O[Si](C)(C)C)=C21	3669.3	Semi standard non polar	33892256
Artobiloxanthone,2TMS,isomer #5	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C21	3627.6	Semi standard non polar	33892256
Artobiloxanthone,2TMS,isomer #6	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O)=C21	3687.0	Semi standard non polar	33892256
Artobiloxanthone,3TMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O)=C21	3666.7	Semi standard non polar	33892256
Artobiloxanthone,3TMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O)C(O[Si](C)(C)C)=C21	3631.6	Semi standard non polar	33892256
Artobiloxanthone,3TMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C21	3581.0	Semi standard non polar	33892256
Artobiloxanthone,3TMS,isomer #4	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C21	3603.2	Semi standard non polar	33892256
Artobiloxanthone,4TMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C21	3597.4	Semi standard non polar	33892256
Artobiloxanthone,1TBDMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C=C(O)C(O)=C21	3974.9	Semi standard non polar	33892256
Artobiloxanthone,1TBDMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C21	3950.7	Semi standard non polar	33892256
Artobiloxanthone,1TBDMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C21	4009.6	Semi standard non polar	33892256
Artobiloxanthone,1TBDMS,isomer #4	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O)=C21	3987.1	Semi standard non polar	33892256
Artobiloxanthone,2TBDMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O)=C21	4086.1	Semi standard non polar	33892256
Artobiloxanthone,2TBDMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C21	4136.6	Semi standard non polar	33892256
Artobiloxanthone,2TBDMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C21	4059.7	Semi standard non polar	33892256
Artobiloxanthone,2TBDMS,isomer #4	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C21	4091.2	Semi standard non polar	33892256
Artobiloxanthone,2TBDMS,isomer #5	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C21	4065.0	Semi standard non polar	33892256
Artobiloxanthone,2TBDMS,isomer #6	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C21	4133.5	Semi standard non polar	33892256
Artobiloxanthone,3TBDMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C21	4257.8	Semi standard non polar	33892256
Artobiloxanthone,3TBDMS,isomer #2	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C21	4225.2	Semi standard non polar	33892256
Artobiloxanthone,3TBDMS,isomer #3	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C21	4165.6	Semi standard non polar	33892256
Artobiloxanthone,3TBDMS,isomer #4	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C21	4180.5	Semi standard non polar	33892256
Artobiloxanthone,4TBDMS,isomer #1	C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C21	4323.3	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 - Artobiloxanthone GC-MS (Non-derivatized) - 70eV, Positive	splash10-066u-1232900000-e84a9cfc02616843c8d7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artobiloxanthone GC-MS (3 TMS) - 70eV, Positive	splash10-000i-1020139000-67d942d2ab4cee2e2bdd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artobiloxanthone 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 - Artobiloxanthone 10V, Positive-QTOF	splash10-000i-0003900000-668be1310d0d6fcb6285	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 20V, Positive-QTOF	splash10-00p0-1109400000-39bbf898fd245c31f0b6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 40V, Positive-QTOF	splash10-02vi-4019000000-5c30c4c85f0d9c4feaf1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 10V, Negative-QTOF	splash10-001i-0000900000-c0372ac112ace47c9156	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 20V, Negative-QTOF	splash10-001i-0004900000-d71552c889e74c89b61b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 40V, Negative-QTOF	splash10-002b-0029100000-ac17fcf0d204d9708d44	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 10V, Positive-QTOF	splash10-000i-0000900000-8c5edb9d93203123adad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 20V, Positive-QTOF	splash10-000i-0000900000-8c5edb9d93203123adad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 40V, Positive-QTOF	splash10-014r-0092500000-0f680dca4ab4f1c8f6b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 10V, Negative-QTOF	splash10-001i-0000900000-81a03ca7359d4e6c5e6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 20V, Negative-QTOF	splash10-001i-0000900000-81a03ca7359d4e6c5e6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artobiloxanthone 40V, Negative-QTOF	splash10-0api-0190200000-eca206f39d98b7f654e8	2021-09-24	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

FDB012259

KNApSAcK ID

C00004104

Chemspider ID

24673270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10071572

PDB ID

Not Available

ChEBI ID

172673

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1839871

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 Artobiloxanthone (HMDB0034021)

MOL for HMDB0034021 (Artobiloxanthone)

3D MOL for HMDB0034021 (Artobiloxanthone)

3D SDF for HMDB0034021 (Artobiloxanthone)

3D-SDF for HMDB0034021 (Artobiloxanthone)

PDB for HMDB0034021 (Artobiloxanthone)

3D PDB for HMDB0034021 (Artobiloxanthone)

SMILES for HMDB0034021 (Artobiloxanthone)

INCHI for HMDB0034021 (Artobiloxanthone)

Structure for HMDB0034021 (Artobiloxanthone)

3D Structure for HMDB0034021 (Artobiloxanthone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra