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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:05 UTC

Update Date

2022-03-07 02:52:34 UTC

HMDB ID

HMDB0030487

Secondary Accession Numbers

HMDB30487

Metabolite Identification

Common Name

Artonol A

Description

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

Structure

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


  Mrv0541 05061305152D          

 26 29  0  0  0  0            999 V2000
    8.7989    1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5288    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5274    0.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269    1.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2588    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583    2.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    4.1446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    0.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    3.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    2.2736    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  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  5  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  2  0  0  0  0
 19 15  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  2  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21  6  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 24 18  2  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 16  1  0  0  0  0
 26 21  1  0  0  0  0
M  END

HMDB0030487
     RDKit          3D
Artonol A
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.8953    1.0069    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327   -0.1130    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -1.1647    1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8778   -0.3900    0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698   -0.7145    1.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190   -0.4087    1.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869   -0.5202    3.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945    0.0140    0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1989   -0.1333    0.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    0.2580   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930    0.0621   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024    0.4495   -1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5422    1.0438   -2.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500    1.2592   -2.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6621    1.8514   -3.5479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    0.8532   -1.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    1.0373   -1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6086    1.5680   -2.3291 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    0.6019   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1797    0.7683   -0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4660    0.2249   -1.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -0.3678   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1647    0.4805    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7350   -1.6617   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553   -0.7627    1.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8542   -0.5654    0.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2761    1.7783   -0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542    1.2115    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8883   -2.1793    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2428   -1.0259    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1273   -1.1453    2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829   -1.2651   -0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9761   -0.2963    2.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4496   -1.8360    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1740    1.3500   -3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    2.0795   -3.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3711    1.6872    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314    0.9615   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7221   -0.1852    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7264    1.2815    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8818    0.8610   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2004   -1.4480   -1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8829   -2.3594   -0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4358   -2.0391    0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6029   -1.2306    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2155   -0.8775    1.8117 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  2  0
 20  4  1  0
 19  8  2  0
 16 10  1  0
 26 11  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
 13 35  1  0
 15 36  1  0
 20 37  1  0
 20 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
M  END


  Mrv0541 05061305152D          

 26 29  0  0  0  0            999 V2000
    8.7989    1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5288    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5274    0.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269    1.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    3.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2588    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583    2.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    4.1446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    0.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    3.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182    1.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    2.2736    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  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  5  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  2  0  0  0  0
 19 15  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  2  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21  6  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 24 18  2  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 16  1  0  0  0  0
 26 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030487

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CC(=O)C2=C(C1)C(=O)C1=C(O2)C2=C(OC(C)(C)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O5/c1-10(2)11-7-13-18(24)17-14(22)9-16-12(5-6-21(3,4)26-16)20(17)25-19(13)15(23)8-11/h5-6,9,11,22H,1,7-8H2,2-4H3

> <INCHI_KEY>
XCESLDIMJGQRPW-UHFFFAOYSA-N

> <FORMULA>
C21H20O5

> <MOLECULAR_WEIGHT>
352.3805

> <EXACT_MASS>
352.13107375

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.075045084331705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-hydroxy-2,2-dimethyl-8-(prop-1-en-2-yl)-2,6,7,8,9,10-hexahydro-1,5-dioxatetraphene-6,10-dione

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
4.177112141666667

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.756896995576835

> <JCHEM_PKA_STRONGEST_BASIC>
-4.831457829686912

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
99.17629999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-2,2-dimethyl-8-(prop-1-en-2-yl)-8,9-dihydro-7H-1,5-dioxatetraphene-6,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030487
     RDKit          3D
Artonol A
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.8953    1.0069    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327   -0.1130    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -1.1647    1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8778   -0.3900    0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698   -0.7145    1.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190   -0.4087    1.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869   -0.5202    3.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945    0.0140    0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1989   -0.1333    0.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    0.2580   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930    0.0621   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024    0.4495   -1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5422    1.0438   -2.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500    1.2592   -2.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6621    1.8514   -3.5479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    0.8532   -1.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    1.0373   -1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6086    1.5680   -2.3291 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    0.6019   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1797    0.7683   -0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4660    0.2249   -1.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -0.3678   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1647    0.4805    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7350   -1.6617   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553   -0.7627    1.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8542   -0.5654    0.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2761    1.7783   -0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542    1.2115    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8883   -2.1793    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2428   -1.0259    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1273   -1.1453    2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829   -1.2651   -0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9761   -0.2963    2.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4496   -1.8360    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1740    1.3500   -3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    2.0795   -3.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3711    1.6872    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314    0.9615   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7221   -0.1852    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7264    1.2815    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8818    0.8610   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2004   -1.4480   -1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8829   -2.3594   -0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4358   -2.0391    0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6029   -1.2306    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2155   -0.8775    1.8117 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  2  0
 20  4  1  0
 19  8  2  0
 16 10  1  0
 26 11  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
 13 35  1  0
 15 36  1  0
 20 37  1  0
 20 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  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      16.425   2.498   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.920   5.117   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.851   1.594   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.477   3.538   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.343   1.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.831   1.625   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.896   4.535   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.400   1.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.343   5.990   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.416   3.662   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.904   3.371   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.847   3.371   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.384   4.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.855   6.281   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.888   1.625   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.839   4.535   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.863   5.117   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.375   5.408   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.880   2.789   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.359   3.662   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.822   2.789   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.359   7.737   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.384   0.170   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.880   6.863   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.367   2.498   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.327   4.244   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   21                                                            
CONECT    4   21                                                            
CONECT    5    6   12                                                       
CONECT    6    5   21                                                       
CONECT    7   11   13                                                       
CONECT    8   11   15                                                       
CONECT    9   14   16                                                       
CONECT   10    1    2   11                                                  
CONECT   11    7    8   10                                                  
CONECT   12    5   16   20                                                  
CONECT   13    7   18   19                                                  
CONECT   14    9   17   22                                                  
CONECT   15    8   19   23                                                  
CONECT   16    9   12   26                                                  
CONECT   17   14   18   20                                                  
CONECT   18   13   17   24                                                  
CONECT   19   13   15   25                                                  
CONECT   20   12   17   25                                                  
CONECT   21    3    4    6   26                                             
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   18                                                            
CONECT   25   19   20                                                       
CONECT   26   16   21                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0030487
HETATM    1  C1  UNL     1       5.895   1.007   0.139  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.333  -0.113   0.540  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.191  -1.165   1.145  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.878  -0.390   0.421  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.370  -0.715   1.805  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.919  -0.409   1.944  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.387  -0.520   3.072  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.094   0.014   0.824  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.199  -0.133   0.784  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.913   0.258  -0.240  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.293   0.062  -0.200  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.102   0.449  -1.242  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.542   1.044  -2.349  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.150   1.259  -2.426  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.662   1.851  -3.548  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.359   0.853  -1.350  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.006   1.037  -1.369  1.00  0.00           C  
HETATM   18  O4  UNL     1       1.609   1.568  -2.329  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.716   0.602  -0.252  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.180   0.768  -0.204  1.00  0.00           C  
HETATM   21  O5  UNL     1      -4.466   0.225  -1.137  1.00  0.00           O  
HETATM   22  C17 UNL     1      -5.075  -0.368  -0.047  1.00  0.00           C  
HETATM   23  C18 UNL     1      -6.165   0.480   0.577  1.00  0.00           C  
HETATM   24  C19 UNL     1      -5.735  -1.662  -0.539  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.155  -0.763   1.040  1.00  0.00           C  
HETATM   26  C21 UNL     1      -2.854  -0.565   0.976  1.00  0.00           C  
HETATM   27  H1  UNL     1       5.276   1.778  -0.303  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.954   1.212   0.224  1.00  0.00           H  
HETATM   29  H3  UNL     1       5.888  -2.179   0.846  1.00  0.00           H  
HETATM   30  H4  UNL     1       7.243  -1.026   0.812  1.00  0.00           H  
HETATM   31  H5  UNL     1       6.127  -1.145   2.266  1.00  0.00           H  
HETATM   32  H6  UNL     1       3.783  -1.265  -0.277  1.00  0.00           H  
HETATM   33  H7  UNL     1       3.976  -0.296   2.612  1.00  0.00           H  
HETATM   34  H8  UNL     1       3.450  -1.836   1.907  1.00  0.00           H  
HETATM   35  H9  UNL     1      -3.174   1.350  -3.170  1.00  0.00           H  
HETATM   36  H10 UNL     1       0.235   2.079  -3.787  1.00  0.00           H  
HETATM   37  H11 UNL     1       3.371   1.687   0.417  1.00  0.00           H  
HETATM   38  H12 UNL     1       3.631   0.962  -1.187  1.00  0.00           H  
HETATM   39  H13 UNL     1      -6.722  -0.185   1.272  1.00  0.00           H  
HETATM   40  H14 UNL     1      -5.726   1.281   1.221  1.00  0.00           H  
HETATM   41  H15 UNL     1      -6.882   0.861  -0.160  1.00  0.00           H  
HETATM   42  H16 UNL     1      -6.200  -1.448  -1.513  1.00  0.00           H  
HETATM   43  H17 UNL     1      -4.883  -2.359  -0.738  1.00  0.00           H  
HETATM   44  H18 UNL     1      -6.436  -2.039   0.218  1.00  0.00           H  
HETATM   45  H19 UNL     1      -4.603  -1.231   1.910  1.00  0.00           H  
HETATM   46  H20 UNL     1      -2.216  -0.877   1.812  1.00  0.00           H  
CONECT    1    2    2   27   28
CONECT    2    3    4
CONECT    3   29   30   31
CONECT    4    5   20   32
CONECT    5    6   33   34
CONECT    6    7    7    8
CONECT    8    9   19   19
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   26
CONECT   12   13   13   21
CONECT   13   14   35
CONECT   14   15   16   16
CONECT   15   36
CONECT   16   17
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   37   38
CONECT   21   22
CONECT   22   23   24   25
CONECT   23   39   40   41
CONECT   24   42   43   44
CONECT   25   26   26   45
CONECT   26   46
END

HMDB0030487
     RDKit          3D
Artonol A
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.8953    1.0069    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327   -0.1130    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -1.1647    1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8778   -0.3900    0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698   -0.7145    1.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190   -0.4087    1.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869   -0.5202    3.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945    0.0140    0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1989   -0.1333    0.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    0.2580   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930    0.0621   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024    0.4495   -1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5422    1.0438   -2.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500    1.2592   -2.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6621    1.8514   -3.5479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    0.8532   -1.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    1.0373   -1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6086    1.5680   -2.3291 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    0.6019   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1797    0.7683   -0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4660    0.2249   -1.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -0.3678   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1647    0.4805    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7350   -1.6617   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553   -0.7627    1.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8542   -0.5654    0.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2761    1.7783   -0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542    1.2115    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8883   -2.1793    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2428   -1.0259    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1273   -1.1453    2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829   -1.2651   -0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9761   -0.2963    2.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4496   -1.8360    1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1740    1.3500   -3.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    2.0795   -3.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3711    1.6872    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314    0.9615   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7221   -0.1852    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7264    1.2815    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8818    0.8610   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2004   -1.4480   -1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8829   -2.3594   -0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4358   -2.0391    0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6029   -1.2306    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2155   -0.8775    1.8117 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  2  0
 20  4  1  0
 19  8  2  0
 16 10  1  0
 26 11  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
 13 35  1  0
 15 36  1  0
 20 37  1  0
 20 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₅

Average Molecular Weight

352.3805

Monoisotopic Molecular Weight

352.13107375

IUPAC Name

11-hydroxy-2,2-dimethyl-8-(prop-1-en-2-yl)-2,6,7,8,9,10-hexahydro-1,5-dioxatetraphene-6,10-dione

Traditional Name

11-hydroxy-2,2-dimethyl-8-(prop-1-en-2-yl)-8,9-dihydro-7H-1,5-dioxatetraphene-6,10-dione

CAS Registry Number

186824-57-7

SMILES

CC(=C)C1CC(=O)C2=C(C1)C(=O)C1=C(O2)C2=C(OC(C)(C)C=C2)C=C1O

InChI Identifier

InChI=1S/C21H20O5/c1-10(2)11-7-13-18(24)17-14(22)9-16-12(5-6-21(3,4)26-16)20(17)25-19(13)15(23)8-11/h5-6,9,11,22H,1,7-8H2,2-4H3

InChI Key

XCESLDIMJGQRPW-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
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ketone
Ether
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030487)

Cellular substructure

Membrane (HMDB: HMDB0030487)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030487)

Source

Endogenous

Endogenous (HMDB: HMDB0030487)

Plant

Plant (HMDB: HMDB0030487)

Exogenous

Food

Food (HMDB: HMDB0030487)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	189 - 196 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.29 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	3.36	ALOGPS
logP	4.18	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.76	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.18 m³·mol⁻¹	ChemAxon
Polarizability	38.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	184.256	31661259
DarkChem	[M-H]-	180.073	31661259
DeepCCS	[M+H]+	186.687	30932474
DeepCCS	[M-H]-	184.329	30932474
DeepCCS	[M-2H]-	218.417	30932474
DeepCCS	[M+Na]+	193.575	30932474
AllCCS	[M+H]+	184.3	32859911
AllCCS	[M+H-H2O]+	181.2	32859911
AllCCS	[M+NH4]+	187.2	32859911
AllCCS	[M+Na]+	188.0	32859911
AllCCS	[M-H]-	190.0	32859911
AllCCS	[M+Na-2H]-	189.8	32859911
AllCCS	[M+HCOO]-	189.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artonol A	CC(=C)C1CC(=O)C2=C(C1)C(=O)C1=C(O2)C2=C(OC(C)(C)C=C2)C=C1O	3926.0	Standard polar	33892256
Artonol A	CC(=C)C1CC(=O)C2=C(C1)C(=O)C1=C(O2)C2=C(OC(C)(C)C=C2)C=C1O	3138.1	Standard non polar	33892256
Artonol A	CC(=C)C1CC(=O)C2=C(C1)C(=O)C1=C(O2)C2=C(OC(C)(C)C=C2)C=C1O	3202.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artonol A,1TMS,isomer #1	C=C(C)C1CC(=O)C2=C(C1)C(=O)C1=C(O[Si](C)(C)C)C=C3OC(C)(C)C=CC3=C1O2	3026.2	Semi standard non polar	33892256
Artonol A,1TBDMS,isomer #1	C=C(C)C1CC(=O)C2=C(C1)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C3OC(C)(C)C=CC3=C1O2	3233.6	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 - Artonol A GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-4149000000-58e73c2cafebf6d45605	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artonol A GC-MS (1 TMS) - 70eV, Positive	splash10-0597-6239400000-761b55e5b8b5480d85ce	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artonol A 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 - Artonol A 10V, Positive-QTOF	splash10-0udi-0009000000-93576a9de78cf2c55b35	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 20V, Positive-QTOF	splash10-0uy0-4039000000-9fa91bc39fe68a6e2340	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 40V, Positive-QTOF	splash10-014j-8191000000-4616c42e2c5fe3939153	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 10V, Negative-QTOF	splash10-0udi-0009000000-05e950535d99753785c9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 20V, Negative-QTOF	splash10-0udi-0029000000-ccc5cc6a4626168ec5ba	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 40V, Negative-QTOF	splash10-00lr-1691000000-d9db25d602b3fbec636c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 10V, Negative-QTOF	splash10-0udi-0009000000-05df88930ebcf3252a3c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 20V, Negative-QTOF	splash10-0udi-0009000000-9e60e678a2d4d392289d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 40V, Negative-QTOF	splash10-05fu-0968000000-13ee061971cd86300ce9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 10V, Positive-QTOF	splash10-0udi-0009000000-34969c2c3406a9f97297	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 20V, Positive-QTOF	splash10-0udi-0009000000-e1a0596c3084b026e642	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonol A 40V, Positive-QTOF	splash10-000f-2194000000-ab1fd78481232be07b94	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

FDB002356

KNApSAcK ID

C00029739

Chemspider ID

8912048

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10736715

PDB ID

Not Available

ChEBI ID

562842

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1820371

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 Artonol A (HMDB0030487)

MOL for HMDB0030487 (Artonol A)

3D MOL for HMDB0030487 (Artonol A)

3D SDF for HMDB0030487 (Artonol A)

3D-SDF for HMDB0030487 (Artonol A)

PDB for HMDB0030487 (Artonol A)

3D PDB for HMDB0030487 (Artonol A)

SMILES for HMDB0030487 (Artonol A)

INCHI for HMDB0030487 (Artonol A)

Structure for HMDB0030487 (Artonol A)

3D Structure for HMDB0030487 (Artonol A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra