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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:46 UTC

Update Date

2022-03-07 02:52:40 UTC

HMDB ID

HMDB0030742

Secondary Accession Numbers

HMDB30742

Metabolite Identification

Common Name

Helipyrone

Description

Helipyrone belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Based on a literature review a small amount of articles have been published on Helipyrone.

Structure

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

HMDB0030742
     RDKit          3D
Helipyrone
 43 44  0  0  0  0  0  0  0  0999 V2000
    4.5631   -0.6209    2.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532    0.7119    1.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738    0.8320    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534    1.5691    1.1585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2685    1.7214    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3857    2.4552    0.8901 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    1.1105   -0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388    1.3275   -1.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    0.8819   -1.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735   -0.4114   -0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9435   -1.4503   -1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556   -0.7380   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364   -2.1706   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8897    0.2924   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2613    0.0052    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2313   -0.4410    1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4754    1.5239   -0.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020    1.8486   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507    3.0693   -0.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    0.3269   -1.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812   -0.3440   -2.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3284    0.1783   -0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550   -0.6855   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2633   -0.5204    3.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9351   -1.4525    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602   -0.7809    2.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4648    1.4940    2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5002    0.9030    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417    2.4295   -1.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1247    0.8927   -2.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -1.4085   -1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4147   -2.5463    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786   -2.7869   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -2.3710   -0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8629    0.9608    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8219   -0.6912   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3944    0.0865    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1877   -0.1007    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1653   -1.5398    1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142   -0.9271   -2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830   -0.3788   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780   -0.5033   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -1.7513   -0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
  7 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  3  2  0
 18  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
M  END


  Mrv0541 05061305282D          

 23 24  0  0  0  0            999 V2000
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    4.2868    0.0000    0.0000 C   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608    2.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 12  8  2  0  0  0  0
 13  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15  9  1  0  0  0  0
 15 11  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21 17  2  0  0  0  0
 22 12  1  0  0  0  0
 22 16  1  0  0  0  0
 23 13  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030742

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C(C)C(O)=C(CC2=C(O)C(C)=C(CC)OC2=O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O6/c1-5-12-8(3)14(18)10(16(20)22-12)7-11-15(19)9(4)13(6-2)23-17(11)21/h18-19H,5-7H2,1-4H3

> <INCHI_KEY>
BYRZLWJKTOLLBX-UHFFFAOYSA-N

> <FORMULA>
C17H20O6

> <MOLECULAR_WEIGHT>
320.3371

> <EXACT_MASS>
320.125988372

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.79451358641122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-ethyl-3-[(6-ethyl-4-hydroxy-5-methyl-2-oxo-2H-pyran-3-yl)methyl]-4-hydroxy-5-methyl-2H-pyran-2-one

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
-1.018652601842164

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.796756437364051

> <JCHEM_PKA_STRONGEST_ACIDIC>
-10.799153424354976

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6773788588283263

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
87.53679999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-ethyl-3-[(6-ethyl-4-hydroxy-5-methyl-2-oxopyran-3-yl)methyl]-4-hydroxy-5-methylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030742
     RDKit          3D
Helipyrone
 43 44  0  0  0  0  0  0  0  0999 V2000
    4.5631   -0.6209    2.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532    0.7119    1.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738    0.8320    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534    1.5691    1.1585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2685    1.7214    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3857    2.4552    0.8901 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    1.1105   -0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388    1.3275   -1.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    0.8819   -1.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735   -0.4114   -0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9435   -1.4503   -1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556   -0.7380   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364   -2.1706   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8897    0.2924   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2613    0.0052    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2313   -0.4410    1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4754    1.5239   -0.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020    1.8486   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507    3.0693   -0.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    0.3269   -1.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812   -0.3440   -2.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3284    0.1783   -0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550   -0.6855   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2633   -0.5204    3.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9351   -1.4525    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602   -0.7809    2.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4648    1.4940    2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5002    0.9030    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417    2.4295   -1.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1247    0.8927   -2.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -1.4085   -1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4147   -2.5463    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786   -2.7869   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -2.3710   -0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8629    0.9608    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8219   -0.6912   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3944    0.0865    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1877   -0.1007    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1653   -1.5398    1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142   -0.9271   -2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830   -0.3788   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780   -0.5033   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -1.7513   -0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
  7 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  3  2  0
 18  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  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       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.833   4.565   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    8                                                            
CONECT    4    9                                                            
CONECT    5    1   12                                                       
CONECT    6    2   13                                                       
CONECT    7   10   11                                                       
CONECT    8    3   12   14                                                  
CONECT    9    4   13   15                                                  
CONECT   10    7   14   16                                                  
CONECT   11    7   15   17                                                  
CONECT   12    5    8   22                                                  
CONECT   13    6    9   23                                                  
CONECT   14    8   10   18                                                  
CONECT   15    9   11   19                                                  
CONECT   16   10   20   22                                                  
CONECT   17   11   21   23                                                  
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   12   16                                                       
CONECT   23   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0030742
HETATM    1  C1  UNL     1       4.563  -0.621   2.439  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.553   0.712   1.702  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.374   0.832   0.808  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.353   1.569   1.158  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.268   1.721   0.414  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.386   2.455   0.890  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.133   1.111  -0.794  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.039   1.327  -1.638  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.347   0.882  -1.109  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.773  -0.411  -0.959  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.943  -1.450  -1.301  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.056  -0.738  -0.460  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.436  -2.171  -0.328  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.890   0.292  -0.118  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.261   0.005   0.418  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.231  -0.441   1.860  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.475   1.524  -0.265  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.302   1.849  -0.722  1.00  0.00           C  
HETATM   19  O5  UNL     1      -1.951   3.069  -0.849  1.00  0.00           O  
HETATM   20  C15 UNL     1       2.198   0.327  -1.189  1.00  0.00           C  
HETATM   21  O6  UNL     1       2.181  -0.344  -2.412  1.00  0.00           O  
HETATM   22  C16 UNL     1       3.328   0.178  -0.394  1.00  0.00           C  
HETATM   23  C17 UNL     1       4.455  -0.685  -0.881  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.263  -0.520   3.315  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.935  -1.453   1.846  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.560  -0.781   2.869  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.465   1.494   2.504  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.500   0.903   1.171  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.142   2.430  -1.880  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.125   0.893  -2.685  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.037  -1.408  -1.664  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.415  -2.546   0.692  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.679  -2.787  -0.900  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.397  -2.371  -0.876  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.863   0.961   0.397  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.822  -0.691  -0.229  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.394   0.086   2.373  1.00  0.00           H  
HETATM   38  H15 UNL     1      -6.188  -0.101   2.354  1.00  0.00           H  
HETATM   39  H16 UNL     1      -5.165  -1.540   1.978  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.914  -0.927  -2.758  1.00  0.00           H  
HETATM   41  H18 UNL     1       4.683  -0.379  -1.926  1.00  0.00           H  
HETATM   42  H19 UNL     1       5.378  -0.503  -0.301  1.00  0.00           H  
HETATM   43  H20 UNL     1       4.189  -1.751  -0.895  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   22   22
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   20   20
CONECT    8    9   29   30
CONECT    9   10   10   18
CONECT   10   11   12
CONECT   11   31
CONECT   12   13   14   14
CONECT   13   32   33   34
CONECT   14   15   17
CONECT   15   16   35   36
CONECT   16   37   38   39
CONECT   17   18
CONECT   18   19   19
CONECT   20   21   22
CONECT   21   40
CONECT   22   23
CONECT   23   41   42   43
END

HMDB0030742
     RDKit          3D
Helipyrone
 43 44  0  0  0  0  0  0  0  0999 V2000
    4.5631   -0.6209    2.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532    0.7119    1.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738    0.8320    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534    1.5691    1.1585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2685    1.7214    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3857    2.4552    0.8901 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    1.1105   -0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388    1.3275   -1.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    0.8819   -1.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735   -0.4114   -0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9435   -1.4503   -1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556   -0.7380   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364   -2.1706   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8897    0.2924   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2613    0.0052    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2313   -0.4410    1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4754    1.5239   -0.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020    1.8486   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507    3.0693   -0.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    0.3269   -1.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812   -0.3440   -2.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3284    0.1783   -0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550   -0.6855   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2633   -0.5204    3.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9351   -1.4525    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602   -0.7809    2.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4648    1.4940    2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5002    0.9030    1.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417    2.4295   -1.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1247    0.8927   -2.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -1.4085   -1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4147   -2.5463    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786   -2.7869   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -2.3710   -0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8629    0.9608    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8219   -0.6912   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3944    0.0865    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1877   -0.1007    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1653   -1.5398    1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142   -0.9271   -2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830   -0.3788   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780   -0.5033   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -1.7513   -0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
  7 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  3  2  0
 18  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(2,2-Dimethoxyethoxy)-4-methyl-benzene	HMDB
3,3'-Methylenebis[6-ethyl-4-hydroxy-5-methyl-2H-pyran-2-one], 9ci	HMDB
4-(2,2-Dimethoxyethoxy)toluene	HMDB
Acetaldehyde, p-tolyloxy-, dimethylacetal	HMDB
Helipyrone a	HMDB
p-(2,2-Dimethoxyethoxy)toluene	HMDB
p-Methylphenoxyacetaldehyde dimethyl acetal	HMDB

Chemical Formula

C₁₇H₂₀O₆

Average Molecular Weight

320.3371

Monoisotopic Molecular Weight

320.125988372

IUPAC Name

6-ethyl-3-[(6-ethyl-4-hydroxy-5-methyl-2-oxo-2H-pyran-3-yl)methyl]-4-hydroxy-5-methyl-2H-pyran-2-one

Traditional Name

6-ethyl-3-[(6-ethyl-4-hydroxy-5-methyl-2-oxopyran-3-yl)methyl]-4-hydroxy-5-methylpyran-2-one

CAS Registry Number

29902-01-0

SMILES

CCC1=C(C)C(O)=C(CC2=C(O)C(C)=C(CC)OC2=O)C(=O)O1

InChI Identifier

InChI=1S/C17H20O6/c1-5-12-8(3)14(18)10(16(20)22-12)7-11-15(19)9(4)13(6-2)23-17(11)21/h18-19H,5-7H2,1-4H3

InChI Key

BYRZLWJKTOLLBX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030742)
Cytoplasm (HMDB: HMDB0030742)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030742)

Source

Endogenous

Endogenous (HMDB: HMDB0030742)

Plant

Plant (HMDB: HMDB0030742)

Exogenous

Food

Food (HMDB: HMDB0030742)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	218 - 220 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	417.6 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	0.095 g/L	ALOGPS
logP	1.97	ALOGPS
logP	-1	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	-11	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.54 m³·mol⁻¹	ChemAxon
Polarizability	32.79 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	174.821	31661259
DarkChem	[M-H]-	172.525	31661259
DeepCCS	[M+H]+	176.185	30932474
DeepCCS	[M-H]-	173.826	30932474
DeepCCS	[M-2H]-	207.327	30932474
DeepCCS	[M+Na]+	182.554	30932474
AllCCS	[M+H]+	175.4	32859911
AllCCS	[M+H-H2O]+	172.0	32859911
AllCCS	[M+NH4]+	178.6	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	180.0	32859911
AllCCS	[M+Na-2H]-	180.2	32859911
AllCCS	[M+HCOO]-	180.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Helipyrone	CCC1=C(C)C(O)=C(CC2=C(O)C(C)=C(CC)OC2=O)C(=O)O1	3813.0	Standard polar	33892256
Helipyrone	CCC1=C(C)C(O)=C(CC2=C(O)C(C)=C(CC)OC2=O)C(=O)O1	2605.3	Standard non polar	33892256
Helipyrone	CCC1=C(C)C(O)=C(CC2=C(O)C(C)=C(CC)OC2=O)C(=O)O1	2790.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Helipyrone,1TMS,isomer #1	CCC1=C(C)C(O)=C(CC2=C(O[Si](C)(C)C)C(C)=C(CC)OC2=O)C(=O)O1	2582.8	Semi standard non polar	33892256
Helipyrone,2TMS,isomer #1	CCC1=C(C)C(O[Si](C)(C)C)=C(CC2=C(O[Si](C)(C)C)C(C)=C(CC)OC2=O)C(=O)O1	2599.9	Semi standard non polar	33892256
Helipyrone,1TBDMS,isomer #1	CCC1=C(C)C(O)=C(CC2=C(O[Si](C)(C)C(C)(C)C)C(C)=C(CC)OC2=O)C(=O)O1	2813.7	Semi standard non polar	33892256
Helipyrone,2TBDMS,isomer #1	CCC1=C(C)C(O[Si](C)(C)C(C)(C)C)=C(CC2=C(O[Si](C)(C)C(C)(C)C)C(C)=C(CC)OC2=O)C(=O)O1	3102.6	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 - Helipyrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0avl-2559000000-597dc753152f954262b6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Helipyrone GC-MS (2 TMS) - 70eV, Positive	splash10-0002-4012900000-5567dbe47c21b7bc1160	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Helipyrone 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 - Helipyrone , positive-QTOF	splash10-0a4i-0900000000-4f134174b8228e2f3d08	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 10V, Positive-QTOF	splash10-00di-0209000000-fbc61b0b321b64cdfe6c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 20V, Positive-QTOF	splash10-01b9-4926000000-60d8a0bf3864e2606e97	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 40V, Positive-QTOF	splash10-0aou-5900000000-cf0a97975cfbde68b15c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 10V, Negative-QTOF	splash10-014i-1149000000-8cbdd7e8c96153b2b3bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 20V, Negative-QTOF	splash10-0uxr-1922000000-4fff93336dc7499a9b68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 40V, Negative-QTOF	splash10-0aor-6950000000-cb1d23fed6895e30b986	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 10V, Positive-QTOF	splash10-00di-0209000000-50c2e324263c7f87c93c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 20V, Positive-QTOF	splash10-0avr-0902000000-85afd6569acdb85acc09	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 40V, Positive-QTOF	splash10-0fw9-2940000000-7f8d038b5dddbe5b8888	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 10V, Negative-QTOF	splash10-014i-0019000000-5ef38c0e5d586c558f7b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 20V, Negative-QTOF	splash10-0690-0493000000-554b7c858a0fe2ff7a6e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helipyrone 40V, Negative-QTOF	splash10-0fa9-3910000000-8969a552b699aa77fd5e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB002670

KNApSAcK ID

Not Available

Chemspider ID

23281708

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54709865

PDB ID

Not Available

ChEBI ID

475114

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1822421

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Helipyrone (HMDB0030742)

MOL for HMDB0030742 (Helipyrone)

3D MOL for HMDB0030742 (Helipyrone)

3D SDF for HMDB0030742 (Helipyrone)

3D-SDF for HMDB0030742 (Helipyrone)

PDB for HMDB0030742 (Helipyrone)

3D PDB for HMDB0030742 (Helipyrone)

SMILES for HMDB0030742 (Helipyrone)

INCHI for HMDB0030742 (Helipyrone)

Structure for HMDB0030742 (Helipyrone)

3D Structure for HMDB0030742 (Helipyrone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra