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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:02 UTC

Update Date

2022-03-07 02:52:12 UTC

HMDB ID

HMDB0029540

Secondary Accession Numbers

HMDB29540

Metabolite Identification

Common Name

Nobiletin

Description

Nobiletin 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, nobiletin is considered to be a flavonoid. Nobiletin is a bitter tasting compound. Nobiletin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Nobiletin has also been detected, but not quantified in, several different foods, such as citrus, grapefruits (Citrus X paradisi), lemons (Citrus limon), mandarin orange (clementine, tangerine), and sweet bays (Laurus nobilis). This could make nobiletin a potential biomarker for the consumption of these foods. Nobiletin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Nobiletin.

Structure

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

  Mrv0541 02241217282D          

 29 31  0  0  0  0            999 V2000
    1.4023   -0.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -2.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    2.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422    2.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -2.5573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -3.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821   -3.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -2.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -3.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -0.9897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    3.5474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448   -1.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  2 29  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  2  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 26  1  0  0  0  0
 15 16  1  0  0  0  0
 15 28  2  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0029540
     RDKit          3D
Nobiletin
 51 53  0  0  0  0  0  0  0  0999 V2000
    6.8529    2.2815   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691    0.9313   -0.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1184    0.5815   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1328    1.5436   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7976    1.1473    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4440   -0.1821    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -0.5369    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984   -1.8429    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7623   -2.1522    0.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813   -3.3326    0.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -1.0902    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0148   -1.2682    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4809   -2.5835    0.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7721   -3.2957   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -0.2077    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569   -0.4296    0.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9873   -0.4984    1.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325    1.0870    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3192    2.1778    0.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8358    2.6725   -0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0755    1.2792    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6002    2.5782    0.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3913    3.2487   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1766    0.2044    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    0.3875    0.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533   -1.1050    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7904   -0.7520    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7997   -1.7189    0.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324   -3.0923    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9669    2.3010   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125    2.9176    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6944    2.7083   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065    2.5889   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153    1.8857    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898   -2.6732    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8089   -3.1186   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064   -2.9882   -1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6058   -4.3591   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0398   -0.1959    1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0417   -1.5386    2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6080    0.1338    2.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0231    3.7563   -0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8102    2.1585   -1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1092    2.4866   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    2.5659   -1.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836    4.0431   -1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4095    3.7476   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197   -2.1465    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2931   -3.7405    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7668   -3.1876    0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9462   -3.3772   -0.8345 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
  6 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 27  3  1  0
 25  7  1  0
 24 11  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 26 48  1  0
 29 49  1  0
 29 50  1  0
 29 51  1  0
M  END

  Mrv0541 02241217282D          

 29 31  0  0  0  0            999 V2000
    1.4023   -0.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -2.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -0.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    2.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422    2.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023    2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -2.5573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -3.3823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821   -3.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -2.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -3.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -0.9897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -1.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422    3.5474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448   -1.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  2 29  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  2  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 26  1  0  0  0  0
 15 16  1  0  0  0  0
 15 28  2  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029540

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3

> <INCHI_KEY>
MRIAQLRQZPPODS-UHFFFAOYSA-N

> <FORMULA>
C21H22O8

> <MOLECULAR_WEIGHT>
402.3946

> <EXACT_MASS>
402.13146768

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
41.794221040798135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.021357504666666

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.127322121782655

> <JCHEM_PKA_STRONGEST_BASIC>
-4.144891533145286

> <JCHEM_POLAR_SURFACE_AREA>
81.68

> <JCHEM_REFRACTIVITY>
105.75039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nobiletin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029540
     RDKit          3D
Nobiletin
 51 53  0  0  0  0  0  0  0  0999 V2000
    6.8529    2.2815   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691    0.9313   -0.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1184    0.5815   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1328    1.5436   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7976    1.1473    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4440   -0.1821    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -0.5369    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984   -1.8429    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7623   -2.1522    0.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813   -3.3326    0.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -1.0902    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0148   -1.2682    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4809   -2.5835    0.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7721   -3.2957   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -0.2077    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569   -0.4296    0.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9873   -0.4984    1.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325    1.0870    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3192    2.1778    0.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8358    2.6725   -0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0755    1.2792    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6002    2.5782    0.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3913    3.2487   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1766    0.2044    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    0.3875    0.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533   -1.1050    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7904   -0.7520    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7997   -1.7189    0.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324   -3.0923    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9669    2.3010   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125    2.9176    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6944    2.7083   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065    2.5889   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153    1.8857    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898   -2.6732    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8089   -3.1186   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064   -2.9882   -1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6058   -4.3591   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0398   -0.1959    1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0417   -1.5386    2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6080    0.1338    2.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0231    3.7563   -0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8102    2.1585   -1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1092    2.4866   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    2.5659   -1.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836    4.0431   -1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4095    3.7476   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197   -2.1465    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2931   -3.7405    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7668   -3.1876    0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9462   -3.3772   -0.8345 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
  6 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 27  3  1  0
 25  7  1  0
 24 11  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 26 48  1  0
 29 49  1  0
 29 50  1  0
 29 51  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       2.618  -0.309   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.618  -1.847   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.385  -2.618   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.385  -4.158   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.001  -4.928   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.385  -4.158   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.385  -2.618   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.001  -1.847   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.001  -0.309   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.385   0.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.385   2.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.618   2.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.618   4.312   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.385   5.082   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.001   4.312   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.385   5.082   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.618   4.312   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.771  -4.774   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.080  -6.314   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.153  -6.468   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.923  -7.546   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.618  -4.928   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.771  -6.468   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.618  -1.847   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.004  -2.463   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.385   6.622   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.155   7.546   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.001   2.771   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.004  -2.463   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   29                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8   24                                                  
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    4   19                                                       
CONECT   19   18                                                            
CONECT   20    5   21                                                       
CONECT   21   20                                                            
CONECT   22    6   23                                                       
CONECT   23   22                                                            
CONECT   24    7   25                                                       
CONECT   25   24                                                            
CONECT   26   14   27                                                       
CONECT   27   26                                                            
CONECT   28   11   15                                                       
CONECT   29    2                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0029540
HETATM    1  C1  UNL     1       6.853   2.281  -0.247  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.469   0.931  -0.158  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.118   0.581  -0.072  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.133   1.544  -0.072  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.798   1.147   0.015  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.444  -0.182   0.102  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.033  -0.537   0.192  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.598  -1.843   0.282  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.762  -2.152   0.366  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.181  -3.333   0.449  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.645  -1.090   0.355  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.015  -1.268   0.433  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.481  -2.584   0.525  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.772  -3.296  -0.657  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.896  -0.208   0.422  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.257  -0.430   0.502  1.00  0.00           O  
HETATM   17  C13 UNL     1      -5.987  -0.498   1.690  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.432   1.087   0.331  1.00  0.00           C  
HETATM   19  O5  UNL     1      -4.319   2.178   0.319  1.00  0.00           O  
HETATM   20  C15 UNL     1      -4.836   2.673  -0.921  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.075   1.279   0.253  1.00  0.00           C  
HETATM   22  O6  UNL     1      -1.600   2.578   0.161  1.00  0.00           O  
HETATM   23  C17 UNL     1      -1.391   3.249  -1.062  1.00  0.00           C  
HETATM   24  C18 UNL     1      -1.177   0.204   0.264  1.00  0.00           C  
HETATM   25  O7  UNL     1       0.102   0.388   0.190  1.00  0.00           O  
HETATM   26  C19 UNL     1       3.453  -1.105   0.100  1.00  0.00           C  
HETATM   27  C20 UNL     1       4.790  -0.752   0.014  1.00  0.00           C  
HETATM   28  O8  UNL     1       5.800  -1.719   0.014  1.00  0.00           O  
HETATM   29  C21 UNL     1       5.432  -3.092   0.104  1.00  0.00           C  
HETATM   30  H1  UNL     1       7.967   2.301  -0.070  1.00  0.00           H  
HETATM   31  H2  UNL     1       6.412   2.918   0.533  1.00  0.00           H  
HETATM   32  H3  UNL     1       6.694   2.708  -1.248  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.407   2.589  -0.140  1.00  0.00           H  
HETATM   34  H5  UNL     1       2.015   1.886   0.016  1.00  0.00           H  
HETATM   35  H6  UNL     1       1.290  -2.673   0.290  1.00  0.00           H  
HETATM   36  H7  UNL     1      -4.809  -3.119  -1.011  1.00  0.00           H  
HETATM   37  H8  UNL     1      -3.106  -2.988  -1.485  1.00  0.00           H  
HETATM   38  H9  UNL     1      -3.606  -4.359  -0.451  1.00  0.00           H  
HETATM   39  H10 UNL     1      -7.040  -0.196   1.449  1.00  0.00           H  
HETATM   40  H11 UNL     1      -6.042  -1.539   2.101  1.00  0.00           H  
HETATM   41  H12 UNL     1      -5.608   0.134   2.503  1.00  0.00           H  
HETATM   42  H13 UNL     1      -5.023   3.756  -0.846  1.00  0.00           H  
HETATM   43  H14 UNL     1      -5.810   2.159  -1.093  1.00  0.00           H  
HETATM   44  H15 UNL     1      -4.109   2.487  -1.730  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.462   2.566  -1.939  1.00  0.00           H  
HETATM   46  H17 UNL     1      -2.184   4.043  -1.147  1.00  0.00           H  
HETATM   47  H18 UNL     1      -0.409   3.748  -1.102  1.00  0.00           H  
HETATM   48  H19 UNL     1       3.220  -2.146   0.166  1.00  0.00           H  
HETATM   49  H20 UNL     1       6.293  -3.740   0.284  1.00  0.00           H  
HETATM   50  H21 UNL     1       4.767  -3.188   0.991  1.00  0.00           H  
HETATM   51  H22 UNL     1       4.946  -3.377  -0.835  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3
CONECT    3    4    4   27
CONECT    4    5   33
CONECT    5    6    6   34
CONECT    6    7   26
CONECT    7    8    8   25
CONECT    8    9   35
CONECT    9   10   10   11
CONECT   11   12   12   24
CONECT   12   13   15
CONECT   13   14
CONECT   14   36   37   38
CONECT   15   16   18   18
CONECT   16   17
CONECT   17   39   40   41
CONECT   18   19   21
CONECT   19   20
CONECT   20   42   43   44
CONECT   21   22   24   24
CONECT   22   23
CONECT   23   45   46   47
CONECT   24   25
CONECT   26   27   27   48
CONECT   27   28
CONECT   28   29
CONECT   29   49   50   51
END

HMDB0029540
     RDKit          3D
Nobiletin
 51 53  0  0  0  0  0  0  0  0999 V2000
    6.8529    2.2815   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691    0.9313   -0.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1184    0.5815   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1328    1.5436   -0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7976    1.1473    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4440   -0.1821    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -0.5369    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984   -1.8429    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7623   -2.1522    0.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813   -3.3326    0.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -1.0902    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0148   -1.2682    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4809   -2.5835    0.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7721   -3.2957   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -0.2077    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569   -0.4296    0.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9873   -0.4984    1.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325    1.0870    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3192    2.1778    0.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8358    2.6725   -0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0755    1.2792    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6002    2.5782    0.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3913    3.2487   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1766    0.2044    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    0.3875    0.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533   -1.1050    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7904   -0.7520    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7997   -1.7189    0.0138 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324   -3.0923    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9669    2.3010   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125    2.9176    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6944    2.7083   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065    2.5889   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0153    1.8857    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898   -2.6732    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8089   -3.1186   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064   -2.9882   -1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6058   -4.3591   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0398   -0.1959    1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0417   -1.5386    2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6080    0.1338    2.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0231    3.7563   -0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8102    2.1585   -1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1092    2.4866   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    2.5659   -1.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836    4.0431   -1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4095    3.7476   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2197   -2.1465    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2931   -3.7405    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7668   -3.1876    0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9462   -3.3772   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6,7,8,3',4'-Hexamethoxyflavone	ChEBI
Hexamethoxyflavone	ChEBI
2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9ci	HMDB
Flavone, 5,6,7,8,3',4'-hexamethoxy	HMDB

Chemical Formula

C₂₁H₂₂O₈

Average Molecular Weight

402.3946

Monoisotopic Molecular Weight

402.13146768

IUPAC Name

2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one

Traditional Name

nobiletin

CAS Registry Number

478-01-3

SMILES

COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC

InChI Identifier

InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3

InChI Key

MRIAQLRQZPPODS-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyflavone (CHEBI:7602 )
flavones (C10112 )
Flavones and Flavonols (LMPK12111468 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029540)
Cell membrane (HMDB: HMDB0029540)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029540)

Source

Endogenous

Endogenous (HMDB: HMDB0029540)

Plant

Plant (HMDB: HMDB0029540)

Exogenous

Food

Food (HMDB: HMDB0029540)

Fruit

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Citrus (FooDB: FOOD00859)

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Exogenous (HMDB: HMDB0029540)

Process

Not Available

Role

Biological role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0029540)
Cancer preventive (HMDB: HMDB0029540)

Agriculture

Pesticide

Fungicide (HMDB: HMDB0029540)

Pesticide (HMDB: HMDB0029540)

Anti-allergic agent (HMDB: HMDB0029540)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	13.39 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	191.253	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001479

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0092 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.02	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	15.13	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	81.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.75 m³·mol⁻¹	ChemAxon
Polarizability	41.79 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]+	196.904	31661259
DarkChem	[M-H]-	197.232	31661259
DeepCCS	[M+H]+	185.949	30932474
DeepCCS	[M-H]-	183.591	30932474
DeepCCS	[M-2H]-	217.369	30932474
DeepCCS	[M+Na]+	192.597	30932474
AllCCS	[M+H]+	194.5	32859911
AllCCS	[M+H-H2O]+	191.6	32859911
AllCCS	[M+NH4]+	197.2	32859911
AllCCS	[M+Na]+	197.9	32859911
AllCCS	[M-H]-	199.8	32859911
AllCCS	[M+Na-2H]-	200.1	32859911
AllCCS	[M+HCOO]-	200.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nobiletin	COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC	4867.9	Standard polar	33892256
Nobiletin	COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC	3362.6	Standard non polar	33892256
Nobiletin	COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC	3362.0	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 - Nobiletin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0109000000-1083a97d47bd665e7e3e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nobiletin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nobiletin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin LC-ESI-qTof , Positive-QTOF	splash10-004i-0001900000-33c32e9e66704097c76a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin LC-ESI-qTof , Positive-QTOF	splash10-00kb-4930000000-6905f538e3d50304566b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , negative-QTOF	splash10-06rf-0039000000-1f10f3c85ebc9576e9e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , positive-QTOF	splash10-0079-0009000000-ec4f0760bcd6e1c1fcec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , positive-QTOF	splash10-0079-0009000000-a07fe56ebf7850515513	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , positive-QTOF	splash10-00dr-0009000000-f517eba98f7a9c2ef6dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , positive-QTOF	splash10-0079-0009000000-26380311919f21cc1264	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , positive-QTOF	splash10-0079-0009000000-a1ea51facc9a617005d9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , positive-QTOF	splash10-0079-0009000000-ed668e0372bef20e7e1e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , positive-QTOF	splash10-0udi-0003900000-abbce9b6fc298b405ea6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , positive-QTOF	splash10-0uki-0009600000-6e113107c7038d9754bf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin Linear Ion Trap , positive-QTOF	splash10-0079-0009000000-c7bb5f00231de5038448	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin , positive-QTOF	splash10-0udi-0017900000-76a74f58aaa8107742e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin , positive-QTOF	splash10-004i-0001900000-33c32e9e66704097c76a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin , positive-QTOF	splash10-00di-1449000000-515986740b5064496d80	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin 10V, Positive-QTOF	splash10-0udi-0001900000-27af360ec486a6c3d9c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin 35V, Positive-QTOF	splash10-0fki-0009200000-4319c91ac3c4b550666e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin 20V, Positive-QTOF	splash10-0uk9-0009700000-3eec55e1b3cc7eef561a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nobiletin 40V, Positive-QTOF	splash10-00di-0129000000-56a5cc483729ca41cd8c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nobiletin 10V, Positive-QTOF	splash10-0udi-0000900000-4cb76fd70e9da24d2d79	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nobiletin 20V, Positive-QTOF	splash10-0udi-0001900000-1e46aabd07d48fdf1812	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nobiletin 40V, Positive-QTOF	splash10-02ml-0249000000-571e1067224eee352140	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nobiletin 10V, Negative-QTOF	splash10-0udi-0000900000-7349cf45f0a975c8fa0d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nobiletin 20V, Negative-QTOF	splash10-0udi-0006900000-635ddb31cf10fc1ba687	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nobiletin 40V, Negative-QTOF	splash10-06rl-0169000000-608732c8f7b6ff235974	2015-04-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nobiletin

METLIN ID

Not Available

PubChem Compound

72344

PDB ID

Not Available

ChEBI ID

7602

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1637331

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. [PubMed:12787887 ]
Kunimasa K, Ikekita M, Sato M, Ohta T, Yamori Y, Ikeda M, Kuranuki S, Oikawa T: Nobiletin, a citrus polymethoxyflavonoid, suppresses multiple angiogenesis-related endothelial cell functions and angiogenesis in vivo. Cancer Sci. 2010 Nov;101(11):2462-9. doi: 10.1111/j.1349-7006.2010.01668.x. [PubMed:20670297 ]
Miyata Y, Sato T, Yano M, Ito A: Activation of protein kinase C betaII/epsilon-c-Jun NH2-terminal kinase pathway and inhibition of mitogen-activated protein/extracellular signal-regulated kinase 1/2 phosphorylation in antitumor invasive activity induced by the polymethoxy flavonoid, nobiletin. Mol Cancer Ther. 2004 Jul;3(7):839-47. [PubMed:15252145 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Nobiletin (HMDB0029540)

MOL for HMDB0029540 (Nobiletin)

3D MOL for HMDB0029540 (Nobiletin)

3D SDF for HMDB0029540 (Nobiletin)

3D-SDF for HMDB0029540 (Nobiletin)

PDB for HMDB0029540 (Nobiletin)

3D PDB for HMDB0029540 (Nobiletin)

SMILES for HMDB0029540 (Nobiletin)

INCHI for HMDB0029540 (Nobiletin)

Structure for HMDB0029540 (Nobiletin)

3D Structure for HMDB0029540 (Nobiletin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra