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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:21:48 UTC

Update Date

2021-09-26 23:07:59 UTC

HMDB ID

HMDB0254175

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Loureirin B

Description

Loureirin b belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, loureirin b is considered to be a flavonoid lipid molecule. Loureirin b is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. This compound has been identified in human blood as reported by (PMID: 31557052 ). Loureirin b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Loureirin B 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

HMDB0254175
     RDKit          3D
Loureirin B
 43 44  0  0  0  0  0  0  0  0999 V2000
    5.7794    0.3117    2.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0496   -0.7659    1.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -0.7367    1.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912    0.3527    1.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.3643    1.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326    1.4597    1.8810 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996    2.6119    2.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8653   -0.7352    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787   -0.7993    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.0394   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -0.1986   -0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -0.9037    0.4358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778    0.4343   -1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7451    0.2714   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5173    0.8705   -2.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9323    1.6542   -3.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6984    2.2628   -4.4901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5667    1.8194   -3.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7964    1.2195   -2.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -1.8288    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144   -2.9464    0.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291   -4.1321   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -1.8466    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -0.0554    2.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2411    0.9587    2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1887    0.9314    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.2298    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    3.0374    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6651    3.3394    2.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961    2.2699    3.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0649   -0.3695    1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -1.8371    0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639   -0.4895   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810    1.0275   -0.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2365   -0.3428   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5919    0.7238   -2.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0860    3.1950   -4.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    2.4443   -4.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181    1.3572   -2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9181   -4.9928   -0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8907   -4.0481   -1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -4.3879    0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335   -2.6914    0.5750 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
  6  7  1  0
  5  8  2  0
  8  9  1  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
 16 18  1  0
 18 19  2  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23  3  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
M  END


  Mrv1533004191519052D          

 23 24  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  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 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254175

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O5/c1-21-14-10-17(22-2)15(18(11-14)23-3)8-9-16(20)12-4-6-13(19)7-5-12/h4-7,10-11,19H,8-9H2,1-3H3

> <INCHI_KEY>
ZPFRAPVRYLGYEC-UHFFFAOYSA-N

> <FORMULA>
C18H20O5

> <MOLECULAR_WEIGHT>
316.353

> <EXACT_MASS>
316.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.98966600393366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)propan-1-one

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.0332227006666668

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.777281698575877

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.776271955997851

> <JCHEM_PKA_STRONGEST_BASIC>
-4.37631429330092

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
87.15420000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
loureirin B

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254175
     RDKit          3D
Loureirin B
 43 44  0  0  0  0  0  0  0  0999 V2000
    5.7794    0.3117    2.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0496   -0.7659    1.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -0.7367    1.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912    0.3527    1.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.3643    1.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326    1.4597    1.8810 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996    2.6119    2.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8653   -0.7352    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787   -0.7993    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.0394   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -0.1986   -0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -0.9037    0.4358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778    0.4343   -1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7451    0.2714   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5173    0.8705   -2.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9323    1.6542   -3.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6984    2.2628   -4.4901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5667    1.8194   -3.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7964    1.2195   -2.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -1.8288    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144   -2.9464    0.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291   -4.1321   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -1.8466    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -0.0554    2.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2411    0.9587    2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1887    0.9314    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.2298    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    3.0374    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6651    3.3394    2.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961    2.2699    3.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0649   -0.3695    1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -1.8371    0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639   -0.4895   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810    1.0275   -0.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2365   -0.3428   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5919    0.7238   -2.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0860    3.1950   -4.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    2.4443   -4.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181    1.3572   -2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9181   -4.9928   -0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8907   -4.0481   -1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -4.3879    0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335   -2.6914    0.5750 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
  6  7  1  0
  5  8  2  0
  8  9  1  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
 16 18  1  0
 18 19  2  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23  3  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20    8   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0254175
HETATM    1  C1  UNL     1       5.779   0.312   2.034  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.050  -0.766   1.515  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.670  -0.737   1.360  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.891   0.353   1.700  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.512   0.364   1.538  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.733   1.460   1.881  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.400   2.612   2.421  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.865  -0.735   1.021  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.579  -0.799   0.824  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.100  -0.039  -0.353  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.574  -0.199  -0.426  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.188  -0.904   0.436  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.378   0.434  -1.472  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.745   0.271  -1.524  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.517   0.871  -2.516  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.932   1.654  -3.487  1.00  0.00           C  
HETATM   17  O4  UNL     1      -5.698   2.263  -4.490  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.567   1.819  -3.438  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.796   1.219  -2.446  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.637  -1.829   0.678  1.00  0.00           C  
HETATM   21  O5  UNL     1       1.014  -2.946   0.157  1.00  0.00           O  
HETATM   22  C17 UNL     1       1.629  -4.132  -0.241  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.004  -1.847   0.836  1.00  0.00           C  
HETATM   24  H1  UNL     1       6.681  -0.055   2.603  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.241   0.959   2.734  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.189   0.931   1.191  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.334   1.230   2.103  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.122   3.037   1.715  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.665   3.339   2.818  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.996   2.270   3.317  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.065  -0.369   1.746  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.968  -1.837   0.752  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.664  -0.489  -1.268  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.881   1.027  -0.258  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.236  -0.343  -0.771  1.00  0.00           H  
HETATM   36  H13 UNL     1      -6.592   0.724  -2.531  1.00  0.00           H  
HETATM   37  H14 UNL     1      -6.086   3.195  -4.353  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.103   2.444  -4.213  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.718   1.357  -2.418  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.918  -4.993  -0.152  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.891  -4.048  -1.324  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.533  -4.388   0.343  1.00  0.00           H  
HETATM   43  H20 UNL     1       3.633  -2.691   0.575  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   27
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   28   29   30
CONECT    8    9   20
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   12   13
CONECT   13   14   14   19
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17   18
CONECT   17   37
CONECT   18   19   19   38
CONECT   19   39
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   40   41   42
CONECT   23   43
END

HMDB0254175
     RDKit          3D
Loureirin B
 43 44  0  0  0  0  0  0  0  0999 V2000
    5.7794    0.3117    2.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0496   -0.7659    1.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702   -0.7367    1.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8912    0.3527    1.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.3643    1.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326    1.4597    1.8810 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996    2.6119    2.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8653   -0.7352    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787   -0.7993    0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.0394   -0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -0.1986   -0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1877   -0.9037    0.4358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778    0.4343   -1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7451    0.2714   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5173    0.8705   -2.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9323    1.6542   -3.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6984    2.2628   -4.4901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5667    1.8194   -3.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7964    1.2195   -2.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6368   -1.8288    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144   -2.9464    0.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291   -4.1321   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -1.8466    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -0.0554    2.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2411    0.9587    2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1887    0.9314    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    1.2298    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    3.0374    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6651    3.3394    2.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961    2.2699    3.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0649   -0.3695    1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -1.8371    0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639   -0.4895   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810    1.0275   -0.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2365   -0.3428   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5919    0.7238   -2.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0860    3.1950   -4.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029    2.4443   -4.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181    1.3572   -2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9181   -4.9928   -0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8907   -4.0481   -1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -4.3879    0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335   -2.6914    0.5750 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
  6  7  1  0
  5  8  2  0
  8  9  1  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
 16 18  1  0
 18 19  2  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23  3  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀O₅

Average Molecular Weight

316.353

Monoisotopic Molecular Weight

316.131073744

IUPAC Name

1-(4-hydroxyphenyl)-3-(2,4,6-trimethoxyphenyl)propan-1-one

Traditional Name

loureirin B

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H20O5/c1-21-14-10-17(22-2)15(18(11-14)23-3)8-9-16(20)12-4-6-13(19)7-5-12/h4-7,10-11,19H,8-9H2,1-3H3

InChI Key

ZPFRAPVRYLGYEC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retro-dihydrochalcones

Alternative Parents

Substituents

Retro-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Butyrophenone
Phenylketone
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ketone
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120604 )

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	3.28	ALOGPS
logP	3.03	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.15 m³·mol⁻¹	ChemAxon
Polarizability	33.99 Å³	ChemAxon
Number of Rings	2	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]+	179.874	30932474
DeepCCS	[M-H]-	177.516	30932474
DeepCCS	[M-2H]-	210.851	30932474
DeepCCS	[M+Na]+	186.078	30932474
AllCCS	[M+H]+	176.2	32859911
AllCCS	[M+H-H2O]+	172.7	32859911
AllCCS	[M+NH4]+	179.4	32859911
AllCCS	[M+Na]+	180.4	32859911
AllCCS	[M-H]-	178.7	32859911
AllCCS	[M+Na-2H]-	178.6	32859911
AllCCS	[M+HCOO]-	178.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Loureirin B	COC1=CC(OC)=C(CCC(=O)C2=CC=C(O)C=C2)C(OC)=C1	4083.3	Standard polar	33892256
Loureirin B	COC1=CC(OC)=C(CCC(=O)C2=CC=C(O)C=C2)C(OC)=C1	2746.1	Standard non polar	33892256
Loureirin B	COC1=CC(OC)=C(CCC(=O)C2=CC=C(O)C=C2)C(OC)=C1	2927.7	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 - Loureirin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0921000000-a236ab2c3fc02ae843ea	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loureirin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loureirin B GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loureirin B GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Loureirin B 10V, Positive-QTOF	splash10-014i-0109000000-700adfc0ab88ee0cd80f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loureirin B 20V, Positive-QTOF	splash10-01b9-0945000000-5e5835391142390f1e5e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loureirin B 40V, Positive-QTOF	splash10-05fs-2940000000-361176d354297dad1089	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loureirin B 10V, Negative-QTOF	splash10-014i-0009000000-23ac50f9ae12ab6825c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loureirin B 20V, Negative-QTOF	splash10-00ku-6964000000-de456de89887e7731937	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loureirin B 40V, Negative-QTOF	splash10-0f6x-7960000000-ab7281ef800932ec9b8f	2021-10-12	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Loureirin B (HMDB0254175)

MOL for HMDB0254175 (Loureirin B)

3D MOL for HMDB0254175 (Loureirin B)

3D SDF for HMDB0254175 (Loureirin B)

3D-SDF for HMDB0254175 (Loureirin B)

PDB for HMDB0254175 (Loureirin B)

3D PDB for HMDB0254175 (Loureirin B)

SMILES for HMDB0254175 (Loureirin B)

INCHI for HMDB0254175 (Loureirin B)

Structure for HMDB0254175 (Loureirin B)

3D Structure for HMDB0254175 (Loureirin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra