Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:55:05 UTC

Update Date

2022-03-07 02:54:40 UTC

HMDB ID

HMDB0035876

Secondary Accession Numbers

HMDB35876

Metabolite Identification

Common Name

Mesuagin

Description

Mesuagin belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. Thus, mesuagin is considered to be a flavonoid. Mesuagin has been detected, but not quantified in, fruits and mammee apples (Mammea americana). This could make mesuagin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Mesuagin.

Structure

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


  Mrv0541 05061308452D          

 29 32  0  0  0  0            999 V2000
    0.9355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  0  0  0  0
 18 16  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  1  0  0  0  0
 21 18  2  0  0  0  0
 21 19  1  0  0  0  0
 22 15  2  0  0  0  0
 22 18  1  0  0  0  0
 23 15  1  0  0  0  0
 23 19  2  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 24 11  1  0  0  0  0
 25 17  2  0  0  0  0
 26 20  2  0  0  0  0
 27 21  1  0  0  0  0
 28 17  1  0  0  0  0
 28 22  1  0  0  0  0
 29 23  1  0  0  0  0
 29 24  1  0  0  0  0
M  END

HMDB0035876
     RDKit          3D
Mesuagin
 51 54  0  0  0  0  0  0  0  0999 V2000
   -2.6872    2.3234    1.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049    2.3797   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1550    3.8390   -0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159    1.9249   -0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1693    2.8180   -0.5675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.5672   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291   -0.4872    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6933   -1.7986    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6499   -2.1157    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -3.3754    0.3287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -3.6920    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -4.9309    0.4266 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775   -2.7523    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877   -1.4164   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518   -0.3787   -0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4456    0.2845    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902    1.2739    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479    1.6062   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1708    0.9595   -1.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220   -0.0330   -1.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5389   -1.0913   -0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1123    0.2463   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1174    1.1384   -0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402   -2.8673    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -2.6074    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -1.2378    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2988   -1.2546   -0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3359   -0.8842    1.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -0.2490    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7110    1.9042    1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0652    1.7481    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430    3.3696    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203    1.7479   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1176    3.9457   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1104    4.5412    0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3474    3.9560   -1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289   -2.9672    0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546    0.0136    1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8493    1.7875    1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4956    2.3878   -0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4670    1.2367   -2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -0.5275   -2.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    2.0789   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2455   -3.8849    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215   -3.4018    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1494   -0.5662   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7230   -0.8842   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672   -2.2626   -1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -0.5020    2.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0494   -0.1250    1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8606   -1.7849    1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  2  0
 22 23  1  0
  8 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 22  6  1  0
 29  7  1  0
 21  9  1  0
 20 15  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
 13 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
M  END


  Mrv0541 05061308452D          

 29 32  0  0  0  0            999 V2000
    0.9355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  0  0  0  0
 18 16  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  1  0  0  0  0
 21 18  2  0  0  0  0
 21 19  1  0  0  0  0
 22 15  2  0  0  0  0
 22 18  1  0  0  0  0
 23 15  1  0  0  0  0
 23 19  2  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 24 11  1  0  0  0  0
 25 17  2  0  0  0  0
 26 20  2  0  0  0  0
 27 21  1  0  0  0  0
 28 17  1  0  0  0  0
 28 22  1  0  0  0  0
 29 23  1  0  0  0  0
 29 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035876

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(=O)C1=C2OC(C)(C)C=CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O5/c1-13(2)20(26)19-21(27)18-16(14-8-6-5-7-9-14)12-17(25)28-22(18)15-10-11-24(3,4)29-23(15)19/h5-13,27H,1-4H3

> <INCHI_KEY>
SVCPILBFQWTZFW-UHFFFAOYSA-N

> <FORMULA>
C24H22O5

> <MOLECULAR_WEIGHT>
390.4285

> <EXACT_MASS>
390.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.99819728159669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-8,8-dimethyl-6-(2-methylpropanoyl)-4-phenyl-2H,8H-pyrano[2,3-f]chromen-2-one

> <ALOGPS_LOGP>
5.05

> <JCHEM_LOGP>
5.2647859173333345

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.041856134206366

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.372194830265133

> <JCHEM_PKA_STRONGEST_BASIC>
-4.966031479863432

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
121.07979999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mesuagin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035876
     RDKit          3D
Mesuagin
 51 54  0  0  0  0  0  0  0  0999 V2000
   -2.6872    2.3234    1.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049    2.3797   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1550    3.8390   -0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159    1.9249   -0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1693    2.8180   -0.5675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.5672   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291   -0.4872    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6933   -1.7986    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6499   -2.1157    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -3.3754    0.3287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -3.6920    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -4.9309    0.4266 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775   -2.7523    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877   -1.4164   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518   -0.3787   -0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4456    0.2845    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902    1.2739    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479    1.6062   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1708    0.9595   -1.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220   -0.0330   -1.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5389   -1.0913   -0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1123    0.2463   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1174    1.1384   -0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402   -2.8673    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -2.6074    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -1.2378    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2988   -1.2546   -0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3359   -0.8842    1.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -0.2490    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7110    1.9042    1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0652    1.7481    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430    3.3696    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203    1.7479   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1176    3.9457   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1104    4.5412    0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3474    3.9560   -1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289   -2.9672    0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546    0.0136    1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8493    1.7875    1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4956    2.3878   -0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4670    1.2367   -2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -0.5275   -2.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    2.0789   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2455   -3.8849    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215   -3.4018    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1494   -0.5662   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7230   -0.8842   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672   -2.2626   -1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -0.5020    2.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0494   -0.1250    1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8606   -1.7849    1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  2  0
 22 23  1  0
  8 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 22  6  1  0
 29  7  1  0
 21  9  1  0
 20 15  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
 13 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.746   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.564   7.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.053  -0.220   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.053   1.760   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.366   6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.826   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.136   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.056   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.366   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.826   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.206   6.105   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.826   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.056   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.056  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.516   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.206   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.564   4.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.746   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.746   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.564   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.874   0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.826  -1.897   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.104   4.771   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.516   4.771   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.516  -0.564   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.104   2.104   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   14                                                       
CONECT    9    7   14                                                       
CONECT   10   11   15                                                       
CONECT   11   10   24                                                       
CONECT   12   16   17                                                       
CONECT   13    1    2   20                                                  
CONECT   14    8    9   16                                                  
CONECT   15   10   22   23                                                  
CONECT   16   12   14   18                                                  
CONECT   17   12   25   28                                                  
CONECT   18   16   21   22                                                  
CONECT   19   20   21   23                                                  
CONECT   20   13   19   26                                                  
CONECT   21   18   19   27                                                  
CONECT   22   15   18   28                                                  
CONECT   23   15   19   29                                                  
CONECT   24    3    4   11   29                                             
CONECT   25   17                                                            
CONECT   26   20                                                            
CONECT   27   21                                                            
CONECT   28   17   22                                                       
CONECT   29   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0035876
HETATM    1  C1  UNL     1      -2.687   2.323   1.154  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.105   2.380  -0.223  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.155   3.839  -0.695  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.716   1.925  -0.305  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.169   2.818  -0.568  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.227   0.567  -0.113  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.129  -0.487   0.096  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.693  -1.799   0.241  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.650  -2.116   0.186  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.043  -3.375   0.329  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.306  -3.692   0.280  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.600  -4.931   0.427  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.278  -2.752   0.081  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.888  -1.416  -0.072  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.852  -0.379  -0.291  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.446   0.284   0.753  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.390   1.274   0.555  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.748   1.606  -0.720  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.171   0.959  -1.801  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.222  -0.033  -1.564  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.539  -1.091  -0.018  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.112   0.246  -0.167  1.00  0.00           C  
HETATM   23  O4  UNL     1       2.117   1.138  -0.359  1.00  0.00           O  
HETATM   24  C20 UNL     1      -1.640  -2.867   0.450  1.00  0.00           C  
HETATM   25  C21 UNL     1      -2.920  -2.607   0.503  1.00  0.00           C  
HETATM   26  C22 UNL     1      -3.430  -1.238   0.355  1.00  0.00           C  
HETATM   27  C23 UNL     1      -4.299  -1.255  -0.924  1.00  0.00           C  
HETATM   28  C24 UNL     1      -4.336  -0.884   1.537  1.00  0.00           C  
HETATM   29  O5  UNL     1      -2.469  -0.249   0.157  1.00  0.00           O  
HETATM   30  H1  UNL     1      -3.711   1.904   1.135  1.00  0.00           H  
HETATM   31  H2  UNL     1      -2.065   1.748   1.855  1.00  0.00           H  
HETATM   32  H3  UNL     1      -2.843   3.370   1.556  1.00  0.00           H  
HETATM   33  H4  UNL     1      -2.720   1.748  -0.905  1.00  0.00           H  
HETATM   34  H5  UNL     1      -3.118   3.946  -1.237  1.00  0.00           H  
HETATM   35  H6  UNL     1      -2.110   4.541   0.149  1.00  0.00           H  
HETATM   36  H7  UNL     1      -1.347   3.956  -1.431  1.00  0.00           H  
HETATM   37  H8  UNL     1       4.329  -2.967   0.034  1.00  0.00           H  
HETATM   38  H9  UNL     1       4.155   0.014   1.778  1.00  0.00           H  
HETATM   39  H10 UNL     1       5.849   1.788   1.389  1.00  0.00           H  
HETATM   40  H11 UNL     1       6.496   2.388  -0.921  1.00  0.00           H  
HETATM   41  H12 UNL     1       5.467   1.237  -2.800  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.781  -0.527  -2.405  1.00  0.00           H  
HETATM   43  H14 UNL     1       2.106   2.079  -0.480  1.00  0.00           H  
HETATM   44  H15 UNL     1      -1.246  -3.885   0.560  1.00  0.00           H  
HETATM   45  H16 UNL     1      -3.622  -3.402   0.659  1.00  0.00           H  
HETATM   46  H17 UNL     1      -5.149  -0.566  -0.732  1.00  0.00           H  
HETATM   47  H18 UNL     1      -3.723  -0.884  -1.773  1.00  0.00           H  
HETATM   48  H19 UNL     1      -4.667  -2.263  -1.127  1.00  0.00           H  
HETATM   49  H20 UNL     1      -3.675  -0.502   2.343  1.00  0.00           H  
HETATM   50  H21 UNL     1      -5.049  -0.125   1.179  1.00  0.00           H  
HETATM   51  H22 UNL     1      -4.861  -1.785   1.890  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4   33
CONECT    3   34   35   36
CONECT    4    5    5    6
CONECT    6    7    7   22
CONECT    7    8   29
CONECT    8    9    9   24
CONECT    9   10   21
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   37
CONECT   14   15   21
CONECT   15   16   16   20
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   40
CONECT   19   20   20   41
CONECT   20   42
CONECT   21   22   22
CONECT   22   23
CONECT   23   43
CONECT   24   25   25   44
CONECT   25   26   45
CONECT   26   27   28   29
CONECT   27   46   47   48
CONECT   28   49   50   51
END

HMDB0035876
     RDKit          3D
Mesuagin
 51 54  0  0  0  0  0  0  0  0999 V2000
   -2.6872    2.3234    1.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049    2.3797   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1550    3.8390   -0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159    1.9249   -0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1693    2.8180   -0.5675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.5672   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291   -0.4872    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6933   -1.7986    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6499   -2.1157    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -3.3754    0.3287 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -3.6920    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -4.9309    0.4266 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775   -2.7523    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877   -1.4164   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518   -0.3787   -0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4456    0.2845    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902    1.2739    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479    1.6062   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1708    0.9595   -1.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220   -0.0330   -1.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5389   -1.0913   -0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1123    0.2463   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1174    1.1384   -0.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402   -2.8673    0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -2.6074    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -1.2378    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2988   -1.2546   -0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3359   -0.8842    1.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -0.2490    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7110    1.9042    1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0652    1.7481    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430    3.3696    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203    1.7479   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1176    3.9457   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1104    4.5412    0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3474    3.9560   -1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289   -2.9672    0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546    0.0136    1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8493    1.7875    1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4956    2.3878   -0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4670    1.2367   -2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -0.5275   -2.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    2.0789   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2455   -3.8849    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215   -3.4018    0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1494   -0.5662   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7230   -0.8842   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672   -2.2626   -1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6750   -0.5020    2.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0494   -0.1250    1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8606   -1.7849    1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  2  0
 22 23  1  0
  8 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 22  6  1  0
 29  7  1  0
 21  9  1  0
 20 15  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
 13 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Hydroxy-6'',6''-dimethyl-6-isobutyryl-4-phenylpyrano[2'',3'':7,8]coumarin	HMDB
5-Hydroxy-6-isobutyryl-8,8-dimethyl-4-phenyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one, 8ci	HMDB
5-Hydroxy-8,8-dimethyl-6-(2-methyl-1-oxopropyl)-4-phenyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one, 9ci	HMDB

Chemical Formula

C₂₄H₂₂O₅

Average Molecular Weight

390.4285

Monoisotopic Molecular Weight

390.146723814

IUPAC Name

5-hydroxy-8,8-dimethyl-6-(2-methylpropanoyl)-4-phenyl-2H,8H-pyrano[2,3-f]chromen-2-one

Traditional Name

mesuagin

CAS Registry Number

21721-08-4

SMILES

CC(C)C(=O)C1=C2OC(C)(C)C=CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O

InChI Identifier

InChI=1S/C24H22O5/c1-13(2)20(26)19-21(27)18-16(14-8-6-5-7-9-14)12-17(25)28-22(18)15-10-11-24(3,4)29-23(15)19/h5-13,27H,1-4H3

InChI Key

SVCPILBFQWTZFW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
Pyranoneoflavonoid
4-phenylcoumarin
Pyranocoumarin
Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Coumarin
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Lactone
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Neoflavonoids (LMPK12100030 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035876)
Cell membrane (HMDB: HMDB0035876)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035876)

Source

Exogenous

Exogenous (HMDB: HMDB0035876)

Food

Food (HMDB: HMDB0035876)

Fruit

Tropical fruit

Mammee apple (FooDB: FOOD00405)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0035876)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035876)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 - 153 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.68 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	0.0048 g/L	ALOGPS
logP	5.05	ALOGPS
logP	5.26	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.37	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	121.08 m³·mol⁻¹	ChemAxon
Polarizability	42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.199	31661259
DarkChem	[M-H]-	189.808	31661259
DeepCCS	[M+H]+	193.159	30932474
DeepCCS	[M-H]-	190.801	30932474
DeepCCS	[M-2H]-	224.699	30932474
DeepCCS	[M+Na]+	199.843	30932474
AllCCS	[M+H]+	193.4	32859911
AllCCS	[M+H-H2O]+	190.5	32859911
AllCCS	[M+NH4]+	196.1	32859911
AllCCS	[M+Na]+	196.8	32859911
AllCCS	[M-H]-	197.8	32859911
AllCCS	[M+Na-2H]-	197.4	32859911
AllCCS	[M+HCOO]-	197.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.65 minutes	32390414
Predicted by Siyang on May 30, 2022	18.8387 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.99 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3249.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	490.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	241.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	218.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	778.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	884.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1672.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	584.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1612.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	544.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	480.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	348.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	412.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mesuagin	CC(C)C(=O)C1=C2OC(C)(C)C=CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O	4134.5	Standard polar	33892256
Mesuagin	CC(C)C(=O)C1=C2OC(C)(C)C=CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O	3106.5	Standard non polar	33892256
Mesuagin	CC(C)C(=O)C1=C2OC(C)(C)C=CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O	3170.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mesuagin,1TMS,isomer #1	CC(C)C(=O)C1=C2OC(C)(C)C=CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O[Si](C)(C)C	3192.8	Semi standard non polar	33892256
Mesuagin,1TBDMS,isomer #1	CC(C)C(=O)C1=C2OC(C)(C)C=CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O[Si](C)(C)C(C)(C)C	3410.1	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 - Mesuagin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udj-1309000000-36e2a22afef5defbd81f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesuagin GC-MS (1 TMS) - 70eV, Positive	splash10-0v4l-4403900000-3ff456181fa2ba0ab5b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesuagin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesuagin 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 - Mesuagin , positive-QTOF	splash10-00dl-0149000000-f738208c77c717d64d17	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 10V, Positive-QTOF	splash10-0006-1009000000-dd84907bc78b9aad5aab	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 20V, Positive-QTOF	splash10-00dl-3009000000-cc3141621507c4f851cf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 40V, Positive-QTOF	splash10-00xu-9015000000-ad0376ecd49394d02919	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 10V, Negative-QTOF	splash10-000i-0009000000-1e717e77fa99dd218df8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 20V, Negative-QTOF	splash10-014i-1009000000-6680852342bea0de36fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 40V, Negative-QTOF	splash10-0kw0-2169000000-2a5ef2c09f04db2ca63b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 10V, Positive-QTOF	splash10-0006-0009000000-fe1ddf2e6fcd95bf64db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 20V, Positive-QTOF	splash10-0006-0009000000-1b956041f14ba1fcc0cf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 40V, Positive-QTOF	splash10-0a5d-0039000000-f35c32c26f13c30e693c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 10V, Negative-QTOF	splash10-000i-0009000000-5e738b5e42a6d6887c5f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 20V, Negative-QTOF	splash10-000i-0009000000-fe4e3b41ffe9ca8f5919	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesuagin 40V, Negative-QTOF	splash10-0kdj-0039000000-bd13879bba142a152fde	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

FDB014657

KNApSAcK ID

C00010223

Chemspider ID

4477686

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319380

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1852241

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Mesuagin → 6-{[8,8-dimethyl-6-(2-methylpropanoyl)-2-oxo-4-phenyl-2H,8H-pyrano[2,3-f]chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Mesuagin (HMDB0035876)

MOL for HMDB0035876 (Mesuagin)

3D MOL for HMDB0035876 (Mesuagin)

3D SDF for HMDB0035876 (Mesuagin)

3D-SDF for HMDB0035876 (Mesuagin)

PDB for HMDB0035876 (Mesuagin)

3D PDB for HMDB0035876 (Mesuagin)

SMILES for HMDB0035876 (Mesuagin)

INCHI for HMDB0035876 (Mesuagin)

Structure for HMDB0035876 (Mesuagin)

3D Structure for HMDB0035876 (Mesuagin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions