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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:55:21 UTC

Update Date

2021-09-26 23:13:23 UTC

HMDB ID

HMDB0257186

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Retusin

Description

Tetramethylquercetin, also known as retusin, belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, tetramethylquercetin is considered to be a flavonoid. Tetramethylquercetin has been detected, but not quantified in, common oreganos (Origanum vulgare) and mandarin orange (clementine, tangerine). This could make tetramethylquercetin a potential biomarker for the consumption of these foods. Tetramethylquercetin 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 very few articles have been published on Tetramethylquercetin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Retusin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Retusin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv0541 02241218342D          

 26 28  0  0  0  0            999 V2000
   -0.3561    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  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 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 24  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  0  0  0  0
 16 17  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 26  1  0  0  0  0
M  END

HMDB0257186
     RDKit          3D
Retusin
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.9495    3.2399    1.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4959    2.0974    1.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6485    1.1069    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -0.0041   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3074   -1.0007   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8427   -2.0825   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -0.8394   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299   -1.7391   -0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742   -2.7723   -1.5069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602   -1.5167   -0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -2.4392   -1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6867   -2.3770   -2.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070   -0.3963   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1702   -0.0207    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    1.2796    0.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449    1.6985    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7932    0.7873    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0882    1.1952    0.9184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3191    2.5189    1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -0.4947    0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007   -1.3783    0.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3308   -2.7002   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -0.8857   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220    0.4558    0.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039    0.2748    0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819    1.2246    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    2.9461    2.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6869    4.0315    1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1641    3.6733    1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070   -0.1326   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5203   -2.8818   -1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362   -2.7422   -2.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0992   -3.1133   -3.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6753   -1.3635   -3.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498    1.9582    0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818    2.7010    1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3849    2.6761    1.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7000    2.6565    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9701    3.2509    0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8314   -2.6048   -1.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2636   -3.2852   -0.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6444   -3.2077    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1309   -1.9019   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630    2.1076    1.1808 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 13 24  1  0
 24 25  1  0
 25 26  2  0
 26  3  1  0
 25  7  1  0
 23 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 26 44  1  0
M  END


  Mrv0541 02241218342D          

 26 28  0  0  0  0            999 V2000
   -0.3561    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  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 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 24  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  0  0  0  0
 16 17  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257186

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C1=CC=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3

> <INCHI_KEY>
HHGPYJLEJGNWJA-UHFFFAOYSA-N

> <FORMULA>
C19H18O7

> <MOLECULAR_WEIGHT>
358.342

> <EXACT_MASS>
358.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
36.65854619221285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
2.706809021333333

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.355926816780547

> <JCHEM_PKA_STRONGEST_BASIC>
-4.282650017831746

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
95.06029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
retusin (flavonol)

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257186
     RDKit          3D
Retusin
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.9495    3.2399    1.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4959    2.0974    1.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6485    1.1069    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -0.0041   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3074   -1.0007   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8427   -2.0825   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -0.8394   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299   -1.7391   -0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742   -2.7723   -1.5069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602   -1.5167   -0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -2.4392   -1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6867   -2.3770   -2.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070   -0.3963   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1702   -0.0207    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    1.2796    0.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449    1.6985    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7932    0.7873    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0882    1.1952    0.9184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3191    2.5189    1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -0.4947    0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007   -1.3783    0.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3308   -2.7002   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -0.8857   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220    0.4558    0.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039    0.2748    0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819    1.2246    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    2.9461    2.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6869    4.0315    1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1641    3.6733    1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070   -0.1326   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5203   -2.8818   -1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362   -2.7422   -2.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0992   -3.1133   -3.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6753   -1.3635   -3.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498    1.9582    0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818    2.7010    1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3849    2.6761    1.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7000    2.6565    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9701    3.2509    0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8314   -2.6048   -1.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2636   -3.2852   -0.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6444   -3.2077    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1309   -1.9019   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630    2.1076    1.1808 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 13 24  1  0
 24 25  1  0
 25 26  2  0
 26  3  1  0
 25  7  1  0
 23 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 26 44  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  O   UNK     0      -0.665   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.665   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.999   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.999   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.666   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.666   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.334   3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.334   4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.337   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.002   3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.667   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.665   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.004  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.669  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.669   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.337   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.002  -1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.337  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.337  -3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.669  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.001   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.336  -1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.336   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11   10   12                                                       
CONECT   12    2   11   13                                                  
CONECT   13   12   14   19                                                  
CONECT   14    4   13                                                       
CONECT   15   16   25                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   13   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   16   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24    6   26                                                       
CONECT   25   15                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0257186
HETATM    1  C1  UNL     1       4.950   3.240   1.772  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.496   2.097   1.133  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.648   1.107   0.600  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.154  -0.004  -0.021  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.307  -1.001  -0.557  1.00  0.00           C  
HETATM    6  O2  UNL     1       4.843  -2.083  -1.162  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.948  -0.839  -0.446  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.030  -1.739  -0.930  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.374  -2.772  -1.507  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.660  -1.517  -0.787  1.00  0.00           C  
HETATM   11  O4  UNL     1      -0.231  -2.439  -1.292  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.687  -2.377  -2.645  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.207  -0.396  -0.158  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.170  -0.021   0.074  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.473   1.280   0.498  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.745   1.698   0.780  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.793   0.787   0.638  1.00  0.00           C  
HETATM   18  O5  UNL     1      -5.088   1.195   0.918  1.00  0.00           O  
HETATM   19  C14 UNL     1      -5.319   2.519   1.341  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.549  -0.495   0.226  1.00  0.00           C  
HETATM   21  O6  UNL     1      -4.601  -1.378   0.093  1.00  0.00           O  
HETATM   22  C16 UNL     1      -4.331  -2.700  -0.334  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.230  -0.886  -0.052  1.00  0.00           C  
HETATM   24  O7  UNL     1       1.122   0.456   0.298  1.00  0.00           O  
HETATM   25  C18 UNL     1       2.404   0.275   0.177  1.00  0.00           C  
HETATM   26  C19 UNL     1       3.282   1.225   0.687  1.00  0.00           C  
HETATM   27  H1  UNL     1       4.419   2.946   2.702  1.00  0.00           H  
HETATM   28  H2  UNL     1       5.687   4.032   1.911  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.164   3.673   1.086  1.00  0.00           H  
HETATM   30  H4  UNL     1       6.207  -0.133  -0.108  1.00  0.00           H  
HETATM   31  H5  UNL     1       4.520  -2.882  -1.598  1.00  0.00           H  
HETATM   32  H6  UNL     1      -1.736  -2.742  -2.628  1.00  0.00           H  
HETATM   33  H7  UNL     1      -0.099  -3.113  -3.216  1.00  0.00           H  
HETATM   34  H8  UNL     1      -0.675  -1.363  -3.052  1.00  0.00           H  
HETATM   35  H9  UNL     1      -0.650   1.958   0.597  1.00  0.00           H  
HETATM   36  H10 UNL     1      -2.982   2.701   1.108  1.00  0.00           H  
HETATM   37  H11 UNL     1      -6.385   2.676   1.598  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.700   2.656   2.274  1.00  0.00           H  
HETATM   39  H13 UNL     1      -4.970   3.251   0.564  1.00  0.00           H  
HETATM   40  H14 UNL     1      -3.831  -2.605  -1.330  1.00  0.00           H  
HETATM   41  H15 UNL     1      -5.264  -3.285  -0.461  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.644  -3.208   0.369  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.131  -1.902  -0.338  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.863   2.108   1.181  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   26
CONECT    4    5   30
CONECT    5    6    7    7
CONECT    6   31
CONECT    7    8   25
CONECT    8    9    9   10
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   32   33   34
CONECT   13   14   24
CONECT   14   15   15   23
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18   20
CONECT   18   19
CONECT   19   37   38   39
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   40   41   42
CONECT   23   43
CONECT   24   25
CONECT   25   26   26
CONECT   26   44
END

HMDB0257186
     RDKit          3D
Retusin
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.9495    3.2399    1.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4959    2.0974    1.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6485    1.1069    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -0.0041   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3074   -1.0007   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8427   -2.0825   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -0.8394   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299   -1.7391   -0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742   -2.7723   -1.5069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602   -1.5167   -0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -2.4392   -1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6867   -2.3770   -2.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070   -0.3963   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1702   -0.0207    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    1.2796    0.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449    1.6985    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7932    0.7873    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0882    1.1952    0.9184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3191    2.5189    1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -0.4947    0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007   -1.3783    0.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3308   -2.7002   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -0.8857   -0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220    0.4558    0.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039    0.2748    0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819    1.2246    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    2.9461    2.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6869    4.0315    1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1641    3.6733    1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070   -0.1326   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5203   -2.8818   -1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362   -2.7422   -2.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0992   -3.1133   -3.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6753   -1.3635   -3.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498    1.9582    0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818    2.7010    1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3849    2.6761    1.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7000    2.6565    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9701    3.2509    0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8314   -2.6048   -1.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2636   -3.2852   -0.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6444   -3.2077    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1309   -1.9019   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630    2.1076    1.1808 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 13 24  1  0
 24 25  1  0
 25 26  2  0
 26  3  1  0
 25  7  1  0
 23 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 26 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one	ChEBI
3,3',4',7-O-Tetramethylquercetin	ChEBI
3,3',4',7-Tetramethylquercetin	ChEBI
3,7,3',4'-Tetramethylquercetin	ChEBI
Quercetin 3,3',4',7-tetramethyl ether	ChEBI
Quercetin 3,7,3',4'-tetramethyl ether	ChEBI
Retusin	ChEBI
Retusine	ChEBI
5-Hydroxy-3,7,3',4'-tetramethoxyflavone	MetaCyc, MeSH
3,7,3',4'-Tetra-O-methylquercetin	MetaCyc

Chemical Formula

C₁₉H₁₈O₇

Average Molecular Weight

358.342

Monoisotopic Molecular Weight

358.10525293

IUPAC Name

2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one

Traditional Name

retusin (flavonol)

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C1=CC=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3

InChI Key

HHGPYJLEJGNWJA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
3-methoxychromone
Chromone
1-benzopyran
Benzopyran
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112770 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.31	ALOGPS
logP	2.71	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.36	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.06 m³·mol⁻¹	ChemAxon
Polarizability	36.66 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	185.962	30932474
DeepCCS	[M-H]-	183.604	30932474
DeepCCS	[M-2H]-	217.608	30932474
DeepCCS	[M+Na]+	192.837	30932474
AllCCS	[M+H]+	183.6	32859911
AllCCS	[M+H-H2O]+	180.3	32859911
AllCCS	[M+NH4]+	186.6	32859911
AllCCS	[M+Na]+	187.4	32859911
AllCCS	[M-H]-	186.8	32859911
AllCCS	[M+Na-2H]-	186.6	32859911
AllCCS	[M+HCOO]-	186.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retusin	COC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C1=CC=C(OC)C(OC)=C1	4836.1	Standard polar	33892256
Retusin	COC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C1=CC=C(OC)C(OC)=C1	3262.0	Standard non polar	33892256
Retusin	COC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C1=CC=C(OC)C(OC)=C1	3135.8	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 - Retusin GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-0419000000-8001f334e7bd21c10638	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retusin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retusin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retusin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	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 - Retusin 10V, Positive-QTOF	splash10-0a4i-0009000000-95e43140d41719d30219	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retusin 20V, Positive-QTOF	splash10-0a4i-0009000000-577082fa366951f488db	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retusin 40V, Positive-QTOF	splash10-01dr-2966000000-bf2e0d3fb4407ec38faa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retusin 10V, Negative-QTOF	splash10-0a4i-0009000000-8a5664df7dbdeed5c497	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retusin 20V, Negative-QTOF	splash10-0a4i-0029000000-3d02636a4b753879db62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retusin 40V, Negative-QTOF	splash10-02g5-1982000000-9cfa3016640c970c7261	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

FDB017112

KNApSAcK ID

C00004653

Chemspider ID

4508983

KEGG Compound ID

Not Available

BioCyc ID

CPD-14852

BiGG ID

Not Available

Wikipedia Link

Retusin_(flavonol)

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

144861

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1504641

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Retusin (HMDB0257186)

MOL for HMDB0257186 (Retusin)

3D MOL for HMDB0257186 (Retusin)

3D SDF for HMDB0257186 (Retusin)

3D-SDF for HMDB0257186 (Retusin)

PDB for HMDB0257186 (Retusin)

3D PDB for HMDB0257186 (Retusin)

SMILES for HMDB0257186 (Retusin)

INCHI for HMDB0257186 (Retusin)

Structure for HMDB0257186 (Retusin)

3D Structure for HMDB0257186 (Retusin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra