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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:04:57 UTC

Update Date

2022-03-07 02:54:02 UTC

HMDB ID

HMDB0034278

Secondary Accession Numbers

HMDB34278

Metabolite Identification

Common Name

Auranetin

Description

Auranetin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, auranetin is considered to be a flavonoid. Auranetin has been detected, but not quantified in, citrus. This could make auranetin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Auranetin.

Structure

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


  Mrv0541 02241215462D          

 27 29  0  0  0  0            999 V2000
   -1.6718    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -1.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    0.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -1.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1860    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9005    1.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1860    1.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9005   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    1.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718    1.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574    1.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1008    0.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8152   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1008   -1.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1008   -2.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -2.1461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294    1.5665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3295    2.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1860   -1.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9005   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  6  2  0  0  0  0
  7  6  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 23  2  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0034278
     RDKit          3D
Auranetin
 47 49  0  0  0  0  0  0  0  0999 V2000
    6.3796    3.1782   -0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932    2.7593   -1.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3657    2.1591   -1.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    1.7832   -2.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153    1.1678   -2.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332    0.9150   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543    0.2432   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176    0.2640    0.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138   -0.2921    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5883   -0.2086    1.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8533    0.4611    2.7697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258    1.8607    2.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7818   -0.7969    2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2379   -0.7066    3.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8439   -1.7376    4.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5449   -1.4796    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7480   -2.0567    1.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5012   -2.7438    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695   -1.5521   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671   -0.9667   -0.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712   -1.0283   -1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -1.6354   -2.5711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607   -0.4192   -1.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913   -0.5278   -3.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -1.7010   -3.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5387    1.2962   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7749    1.9036   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3098    3.6509   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8674    3.9194    0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7252    2.2824    0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130    1.9739   -3.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9251    0.9280   -3.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    2.2399    3.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868    2.4268    2.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329    1.9817    2.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -1.3407    4.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224   -2.6212    3.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7299   -2.0354    4.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3419   -3.3128    1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8984   -2.0276   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8479   -3.4452   -0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -2.0673   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497   -1.8882   -2.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3238   -2.5180   -3.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860   -1.5540   -4.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    1.0960    0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2657    2.1722    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
  6 26  1  0
 26 27  2  0
 27  3  1  0
 23  7  2  0
 20  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 25 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
M  END


  Mrv0541 02241215462D          

 27 29  0  0  0  0            999 V2000
   -1.6718    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -1.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    0.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -1.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1860    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9005    1.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1860    1.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9005   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    1.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718    1.1540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574    1.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1008    0.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8152   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1008   -1.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1008   -2.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -2.1461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294    1.5665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3295    2.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1860   -1.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9005   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  6  2  0  0  0  0
  7  6  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 23  2  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034278

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=CC(OC)=C(OC)C(OC)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)16-19(25-4)15(21)13-10-14(23-2)18(24-3)20(26-5)17(13)27-16/h6-10H,1-5H3

> <INCHI_KEY>
DGNOHOXRWCCDLK-UHFFFAOYSA-N

> <FORMULA>
C20H20O7

> <MOLECULAR_WEIGHT>
372.3686

> <EXACT_MASS>
372.120902994

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
38.759046955748985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
2.202703077333333

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.215813896208066

> <JCHEM_POLAR_SURFACE_AREA>
72.45

> <JCHEM_REFRACTIVITY>
99.54260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
auranetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034278
     RDKit          3D
Auranetin
 47 49  0  0  0  0  0  0  0  0999 V2000
    6.3796    3.1782   -0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932    2.7593   -1.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3657    2.1591   -1.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    1.7832   -2.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153    1.1678   -2.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332    0.9150   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543    0.2432   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176    0.2640    0.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138   -0.2921    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5883   -0.2086    1.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8533    0.4611    2.7697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258    1.8607    2.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7818   -0.7969    2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2379   -0.7066    3.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8439   -1.7376    4.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5449   -1.4796    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7480   -2.0567    1.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5012   -2.7438    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695   -1.5521   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671   -0.9667   -0.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712   -1.0283   -1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -1.6354   -2.5711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607   -0.4192   -1.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913   -0.5278   -3.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -1.7010   -3.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5387    1.2962   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7749    1.9036   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3098    3.6509   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8674    3.9194    0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7252    2.2824    0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130    1.9739   -3.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9251    0.9280   -3.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    2.2399    3.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868    2.4268    2.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329    1.9817    2.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -1.3407    4.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224   -2.6212    3.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7299   -2.0354    4.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3419   -3.3128    1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8984   -2.0276   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8479   -3.4452   -0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -2.0673   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497   -1.8882   -2.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3238   -2.5180   -3.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860   -1.5540   -4.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    1.0960    0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2657    2.1722    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
  6 26  1  0
 26 27  2  0
 27  3  1  0
 23  7  2  0
 20  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 25 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.121   0.614   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.454  -0.156   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.454  -1.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.121  -2.466   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.787  -1.696   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.787  -0.156   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.453   0.614   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.453  -2.466   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.880  -1.696   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.880  -0.156   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.214   0.614   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.548   2.924   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.214   2.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.548  -0.156   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.881   0.614   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.881   2.154   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.121   2.154   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.787   2.924   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.788   0.614   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -7.122  -0.156   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.788  -2.466   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.788  -4.006   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.453  -4.006   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.215   2.924   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.215   4.464   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.214  -2.466   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.548  -1.696   0.000  0.00  0.00           C+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   23                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9    7   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16                                                       
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   24                                                  
CONECT   17    1   18                                                       
CONECT   18   17                                                            
CONECT   19    2   20                                                       
CONECT   20   19                                                            
CONECT   21    3   22                                                       
CONECT   22   21                                                            
CONECT   23    8                                                            
CONECT   24   16   25                                                       
CONECT   25   24                                                            
CONECT   26    9   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0034278
HETATM    1  C1  UNL     1       6.380   3.178  -0.400  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.593   2.759  -1.489  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.366   2.159  -1.350  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.668   1.783  -2.470  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.415   1.168  -2.420  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.833   0.915  -1.220  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.554   0.243  -1.026  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.018   0.264   0.188  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.114  -0.292   0.498  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.588  -0.209   1.814  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.853   0.461   2.770  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.126   1.861   2.923  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.782  -0.797   2.134  1.00  0.00           C  
HETATM   14  O4  UNL     1      -3.238  -0.707   3.437  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.844  -1.738   4.327  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.545  -1.480   1.190  1.00  0.00           C  
HETATM   17  O5  UNL     1      -4.748  -2.057   1.571  1.00  0.00           O  
HETATM   18  C13 UNL     1      -5.501  -2.744   0.589  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.070  -1.552  -0.087  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.867  -0.967  -0.436  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.371  -1.028  -1.712  1.00  0.00           C  
HETATM   22  O6  UNL     1      -2.040  -1.635  -2.571  1.00  0.00           O  
HETATM   23  C17 UNL     1      -0.161  -0.419  -1.986  1.00  0.00           C  
HETATM   24  O7  UNL     1       0.291  -0.528  -3.299  1.00  0.00           O  
HETATM   25  C18 UNL     1       1.069  -1.701  -3.633  1.00  0.00           C  
HETATM   26  C19 UNL     1       2.539   1.296  -0.079  1.00  0.00           C  
HETATM   27  C20 UNL     1       3.775   1.904  -0.142  1.00  0.00           C  
HETATM   28  H1  UNL     1       7.310   3.651  -0.807  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.867   3.919   0.223  1.00  0.00           H  
HETATM   30  H3  UNL     1       6.725   2.282   0.155  1.00  0.00           H  
HETATM   31  H4  UNL     1       4.113   1.974  -3.437  1.00  0.00           H  
HETATM   32  H5  UNL     1       1.925   0.928  -3.346  1.00  0.00           H  
HETATM   33  H6  UNL     1      -0.807   2.240   3.903  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.687   2.427   2.065  1.00  0.00           H  
HETATM   35  H8  UNL     1      -2.233   1.982   2.866  1.00  0.00           H  
HETATM   36  H9  UNL     1      -2.016  -1.341   4.978  1.00  0.00           H  
HETATM   37  H10 UNL     1      -2.422  -2.621   3.782  1.00  0.00           H  
HETATM   38  H11 UNL     1      -3.730  -2.035   4.930  1.00  0.00           H  
HETATM   39  H12 UNL     1      -6.342  -3.313   1.061  1.00  0.00           H  
HETATM   40  H13 UNL     1      -5.898  -2.028  -0.167  1.00  0.00           H  
HETATM   41  H14 UNL     1      -4.848  -3.445  -0.003  1.00  0.00           H  
HETATM   42  H15 UNL     1      -3.612  -2.067  -0.870  1.00  0.00           H  
HETATM   43  H16 UNL     1       1.850  -1.888  -2.886  1.00  0.00           H  
HETATM   44  H17 UNL     1       0.324  -2.518  -3.725  1.00  0.00           H  
HETATM   45  H18 UNL     1       1.486  -1.554  -4.662  1.00  0.00           H  
HETATM   46  H19 UNL     1       2.077   1.096   0.892  1.00  0.00           H  
HETATM   47  H20 UNL     1       4.266   2.172   0.770  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4   27
CONECT    4    5   31
CONECT    5    6    6   32
CONECT    6    7   26
CONECT    7    8   23   23
CONECT    8    9
CONECT    9   10   10   20
CONECT   10   11   13
CONECT   11   12
CONECT   12   33   34   35
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   36   37   38
CONECT   16   17   19
CONECT   17   18
CONECT   18   39   40   41
CONECT   19   20   20   42
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   25
CONECT   25   43   44   45
CONECT   26   27   27   46
CONECT   27   47
END

HMDB0034278
     RDKit          3D
Auranetin
 47 49  0  0  0  0  0  0  0  0999 V2000
    6.3796    3.1782   -0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932    2.7593   -1.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3657    2.1591   -1.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    1.7832   -2.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4153    1.1678   -2.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332    0.9150   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543    0.2432   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176    0.2640    0.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138   -0.2921    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5883   -0.2086    1.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8533    0.4611    2.7697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258    1.8607    2.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7818   -0.7969    2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2379   -0.7066    3.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8439   -1.7376    4.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5449   -1.4796    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7480   -2.0567    1.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5012   -2.7438    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695   -1.5521   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671   -0.9667   -0.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712   -1.0283   -1.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -1.6354   -2.5711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607   -0.4192   -1.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913   -0.5278   -3.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -1.7010   -3.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5387    1.2962   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7749    1.9036   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3098    3.6509   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8674    3.9194    0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7252    2.2824    0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130    1.9739   -3.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9251    0.9280   -3.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    2.2399    3.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868    2.4268    2.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329    1.9817    2.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -1.3407    4.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224   -2.6212    3.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7299   -2.0354    4.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3419   -3.3128    1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8984   -2.0276   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8479   -3.4452   -0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6123   -2.0673   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8497   -1.8882   -2.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3238   -2.5180   -3.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860   -1.5540   -4.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    1.0960    0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2657    2.1722    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
  6 26  1  0
 26 27  2  0
 27  3  1  0
 23  7  2  0
 20  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 25 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4',6,7,8-Pentamethoxyflavone	HMDB
Aurantin	MeSH, HMDB

Chemical Formula

C₂₀H₂₀O₇

Average Molecular Weight

372.3686

Monoisotopic Molecular Weight

372.120902994

IUPAC Name

3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

auranetin

CAS Registry Number

522-16-7

SMILES

COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=CC(OC)=C(OC)C(OC)=C2O1

InChI Identifier

InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)16-19(25-4)15(21)13-10-14(23-2)18(24-3)20(26-5)17(13)27-16/h6-10H,1-5H3

InChI Key

DGNOHOXRWCCDLK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Flavone
3-methoxychromone
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
Pyranone
Alkyl aryl ether
Pyran
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111612 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034278)

Cellular substructure

Membrane (HMDB: HMDB0034278)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034278)

Source

Exogenous

Food

Food (HMDB: HMDB0034278)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0034278)

Not Available

Nutrient (HMDB: HMDB0034278)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	41.15 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	0.012 g/L	ALOGPS
logP	2.84	ALOGPS
logP	2.2	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.54 m³·mol⁻¹	ChemAxon
Polarizability	38.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.105	31661259
DarkChem	[M-H]-	187.706	31661259
DeepCCS	[M+H]+	185.471	30932474
DeepCCS	[M-H]-	183.114	30932474
DeepCCS	[M-2H]-	217.025	30932474
DeepCCS	[M+Na]+	192.253	30932474
AllCCS	[M+H]+	187.6	32859911
AllCCS	[M+H-H2O]+	184.5	32859911
AllCCS	[M+NH4]+	190.5	32859911
AllCCS	[M+Na]+	191.3	32859911
AllCCS	[M-H]-	191.4	32859911
AllCCS	[M+Na-2H]-	191.3	32859911
AllCCS	[M+HCOO]-	191.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Auranetin	COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=CC(OC)=C(OC)C(OC)=C2O1	4418.3	Standard polar	33892256
Auranetin	COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=CC(OC)=C(OC)C(OC)=C2O1	3157.0	Standard non polar	33892256
Auranetin	COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=CC(OC)=C(OC)C(OC)=C2O1	3142.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Auranetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0219000000-9ee686399a197fc96851	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Auranetin 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 - Auranetin 10V, Positive-QTOF	splash10-00di-0009000000-0ecb060eaa87b3d213cf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 20V, Positive-QTOF	splash10-00di-0009000000-27aa543cff13cc47b7d6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 40V, Positive-QTOF	splash10-03fu-0459000000-b6bdd6425964d501daca	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 10V, Negative-QTOF	splash10-00di-0009000000-55bf8209b4a4b235f6ac	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 20V, Negative-QTOF	splash10-00di-0009000000-20f0f0f1a0ecb19b36ce	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 40V, Negative-QTOF	splash10-0a4i-2490000000-b059ea4686056ef86628	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 10V, Negative-QTOF	splash10-00di-0009000000-c528cfb3e87592b0a62b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 20V, Negative-QTOF	splash10-00di-0029000000-2382023a76e302e4447a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 40V, Negative-QTOF	splash10-0ab9-1922000000-53a082c423c2b403768a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 10V, Positive-QTOF	splash10-00di-0009000000-aa9385dbb205bb238b88	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 20V, Positive-QTOF	splash10-00di-0009000000-9877ae6f6844dab4ca76	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranetin 40V, Positive-QTOF	splash10-03k9-2195000000-30e47aeb9d466c8689a5	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

FDB012615

KNApSAcK ID

C00004657

Chemspider ID

10196

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10643

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1841631

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 Auranetin (HMDB0034278)

MOL for HMDB0034278 (Auranetin)

3D MOL for HMDB0034278 (Auranetin)

3D SDF for HMDB0034278 (Auranetin)

3D-SDF for HMDB0034278 (Auranetin)

PDB for HMDB0034278 (Auranetin)

3D PDB for HMDB0034278 (Auranetin)

SMILES for HMDB0034278 (Auranetin)

INCHI for HMDB0034278 (Auranetin)

Structure for HMDB0034278 (Auranetin)

3D Structure for HMDB0034278 (Auranetin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra