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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:59:31 UTC

Update Date

2022-03-07 02:56:58 UTC

HMDB ID

HMDB0041324

Secondary Accession Numbers

HMDB41324

Metabolite Identification

Common Name

Bisbynin

Description

Bisbynin belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. Bisbynin has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make bisbynin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Bisbynin.

Structure

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

HMDB0041324
     RDKit          3D
Bisbynin
 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.5175    0.9493   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3123   -0.4576   -0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2319   -1.4867   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524   -0.8252    0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    0.2053    1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9997   -0.0282    0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5667   -1.3381    1.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -0.9882   -0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613   -1.0733   -0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2411   -2.3756   -0.4993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.1396   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3061    0.8963    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770    1.9816    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872    1.4116    1.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9853    0.8578    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274    0.4820    0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1728   -0.3718   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4843   -0.9292   -1.5092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    1.0412    1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    1.1019    2.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4342    1.0500   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    1.3547   -1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    1.5762    0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0475   -1.6357   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7248   -2.4642   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6938   -1.1301   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -1.8697    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6090    0.2285    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830    1.1914    0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3356   -1.6878   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249   -0.9404   -1.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2406   -2.4955    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561    2.5965    1.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3682    2.5901   -0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686    1.5976   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8151   -0.2321   -0.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5310    0.0944    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9954    1.4563    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -1.1195    0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2044   -1.5847   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4546    2.0204    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288    0.4901    2.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
  8  6  1  0
 17 11  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

  Mrv0541 05061312342D          

 20 22  0  0  0  0            999 V2000
    1.4289   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.1105    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
    1.0164   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    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
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    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
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15  5  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19  6  1  0  0  0  0
 19  8  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041324

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OCC2=C(C(O)C3OC3(CC=C(C)C)C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-7(2)4-5-15-13(18)9-6-19-8(3)11(16)10(9)12(17)14(15)20-15/h4,8,11-14,16-18H,5-6H2,1-3H3

> <INCHI_KEY>
ICHJNTDKHBXTFN-UHFFFAOYSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.3322

> <EXACT_MASS>
282.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.161892992409427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-methyl-5-(3-methylbut-2-en-1-yl)-4,9-dioxatricyclo[5.4.0.0³,⁵]undec-1(7)-ene-2,6,11-triol

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-0.3856206289999996

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.420746365590432

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.894434714540878

> <JCHEM_PKA_STRONGEST_BASIC>
-3.449839903750929

> <JCHEM_POLAR_SURFACE_AREA>
82.45

> <JCHEM_REFRACTIVITY>
73.4059

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-methyl-5-(3-methylbut-2-en-1-yl)-4,9-dioxatricyclo[5.4.0.0³,⁵]undec-1(7)-ene-2,6,11-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041324
     RDKit          3D
Bisbynin
 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.5175    0.9493   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3123   -0.4576   -0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2319   -1.4867   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524   -0.8252    0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    0.2053    1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9997   -0.0282    0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5667   -1.3381    1.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -0.9882   -0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613   -1.0733   -0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2411   -2.3756   -0.4993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.1396   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3061    0.8963    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770    1.9816    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872    1.4116    1.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9853    0.8578    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274    0.4820    0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1728   -0.3718   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4843   -0.9292   -1.5092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    1.0412    1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    1.1019    2.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4342    1.0500   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    1.3547   -1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    1.5762    0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0475   -1.6357   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7248   -2.4642   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6938   -1.1301   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -1.8697    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6090    0.2285    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830    1.1914    0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3356   -1.6878   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249   -0.9404   -1.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2406   -2.4955    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561    2.5965    1.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3682    2.5901   -0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686    1.5976   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8151   -0.2321   -0.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5310    0.0944    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9954    1.4563    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -1.1195    0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2044   -1.5847   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4546    2.0204    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288    0.4901    2.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
  8  6  1  0
 17 11  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  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  -3.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.357  -2.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.897   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.897  -2.461   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    5    7                                                       
CONECT    5    4   15                                                       
CONECT    6    9   19                                                       
CONECT    7    1    2    4                                                  
CONECT    8    3   11   19                                                  
CONECT    9    6   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11    8   10   16                                                  
CONECT   12   10   14   17                                                  
CONECT   13    9   15   18                                                  
CONECT   14   12   15   20                                                  
CONECT   15    5   13   14   20                                             
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19    6    8                                                       
CONECT   20   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0041324
HETATM    1  C1  UNL     1      -4.517   0.949  -0.770  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.312  -0.458  -0.346  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.232  -1.487  -0.893  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.352  -0.825   0.490  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.446   0.205   1.025  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.000  -0.028   0.677  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.567  -1.338   1.233  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.616  -0.988  -0.213  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.761  -1.073  -0.768  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.241  -2.376  -0.499  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.715  -0.140  -0.119  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.306   0.896   0.592  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.277   1.982   0.896  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.487   1.412   1.208  1.00  0.00           O  
HETATM   15  C12 UNL     1       3.985   0.858   0.005  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.427   0.482   0.284  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.173  -0.372  -0.269  1.00  0.00           C  
HETATM   18  O4  UNL     1       3.484  -0.929  -1.509  1.00  0.00           O  
HETATM   19  C15 UNL     1      -0.064   1.041   1.104  1.00  0.00           C  
HETATM   20  O5  UNL     1      -0.063   1.102   2.503  1.00  0.00           O  
HETATM   21  H1  UNL     1      -5.434   1.050  -1.381  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.629   1.355  -1.304  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.717   1.576   0.147  1.00  0.00           H  
HETATM   24  H4  UNL     1      -6.048  -1.636  -0.136  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.725  -2.464  -1.025  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.694  -1.130  -1.836  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.240  -1.870   0.773  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.609   0.228   2.137  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.783   1.191   0.661  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.336  -1.688  -0.690  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.825  -0.940  -1.845  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.241  -2.495   0.484  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.956   2.597   1.761  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.368   2.590  -0.033  1.00  0.00           H  
HETATM   35  H15 UNL     1       3.969   1.598  -0.812  1.00  0.00           H  
HETATM   36  H16 UNL     1       5.815  -0.232  -0.445  1.00  0.00           H  
HETATM   37  H17 UNL     1       5.531   0.094   1.338  1.00  0.00           H  
HETATM   38  H18 UNL     1       5.995   1.456   0.285  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.448  -1.120   0.530  1.00  0.00           H  
HETATM   40  H20 UNL     1       4.204  -1.585  -1.372  1.00  0.00           H  
HETATM   41  H21 UNL     1      -0.455   2.020   0.758  1.00  0.00           H  
HETATM   42  H22 UNL     1       0.629   0.490   2.894  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    4
CONECT    3   24   25   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7    8   19
CONECT    7    8
CONECT    8    9   30
CONECT    9   10   11   31
CONECT   10   32
CONECT   11   12   12   17
CONECT   12   13   19
CONECT   13   14   33   34
CONECT   14   15
CONECT   15   16   17   35
CONECT   16   36   37   38
CONECT   17   18   39
CONECT   18   40
CONECT   19   20   41
CONECT   20   42
END

HMDB0041324
     RDKit          3D
Bisbynin
 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.5175    0.9493   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3123   -0.4576   -0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2319   -1.4867   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524   -0.8252    0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    0.2053    1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9997   -0.0282    0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5667   -1.3381    1.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -0.9882   -0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613   -1.0733   -0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2411   -2.3756   -0.4993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.1396   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3061    0.8963    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770    1.9816    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872    1.4116    1.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9853    0.8578    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4274    0.4820    0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1728   -0.3718   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4843   -0.9292   -1.5092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643    1.0412    1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0633    1.1019    2.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4342    1.0500   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    1.3547   -1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    1.5762    0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0475   -1.6357   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7248   -2.4642   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6938   -1.1301   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -1.8697    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6090    0.2285    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830    1.1914    0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3356   -1.6878   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249   -0.9404   -1.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2406   -2.4955    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561    2.5965    1.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3682    2.5901   -0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686    1.5976   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8151   -0.2321   -0.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5310    0.0944    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9954    1.4563    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -1.1195    0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2044   -1.5847   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4546    2.0204    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288    0.4901    2.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
  8  6  1  0
 17 11  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1a,3,5,6,7,7a-hexahydro-5-Methyl-1a-(3-methyl-2-butenyl)-2H-oxireno[g][2]benzopyran-2,6,7-triol, 9ci	HMDB

Chemical Formula

C₁₅H₂₂O₅

Average Molecular Weight

282.3322

Monoisotopic Molecular Weight

282.146723814

IUPAC Name

10-methyl-5-(3-methylbut-2-en-1-yl)-4,9-dioxatricyclo[5.4.0.0³,⁵]undec-1(7)-ene-2,6,11-triol

Traditional Name

10-methyl-5-(3-methylbut-2-en-1-yl)-4,9-dioxatricyclo[5.4.0.0³,⁵]undec-1(7)-ene-2,6,11-triol

CAS Registry Number

163365-14-8

SMILES

CC1OCC2=C(C(O)C3OC3(CC=C(C)C)C2O)C1O

InChI Identifier

InChI=1S/C15H22O5/c1-7(2)4-5-15-13(18)9-6-19-8(3)11(16)10(9)12(17)14(15)20-15/h4,8,11-14,16-18H,5-6H2,1-3H3

InChI Key

ICHJNTDKHBXTFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Not Available

Direct Parent

Pyrans

Alternative Parents

Substituents

Pyran
Secondary alcohol
Oxacycle
Polyol
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041324)
Cytoplasm (HMDB: HMDB0041324)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041324)

Source

Exogenous

Exogenous (HMDB: HMDB0041324)

Food

Food (HMDB: HMDB0041324)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0041324)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Emulsifier (HMDB: HMDB0041324)

Biological role

Nutrient (HMDB: HMDB0041324)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	144 °C	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
Water Solubility	8.74 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	-0.39	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.41 m³·mol⁻¹	ChemAxon
Polarizability	30.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.309	31661259
DarkChem	[M-H]-	162.261	31661259
DeepCCS	[M+H]+	169.707	30932474
DeepCCS	[M-H]-	167.349	30932474
DeepCCS	[M-2H]-	200.252	30932474
DeepCCS	[M+Na]+	175.8	30932474
AllCCS	[M+H]+	169.3	32859911
AllCCS	[M+H-H2O]+	165.9	32859911
AllCCS	[M+NH4]+	172.4	32859911
AllCCS	[M+Na]+	173.3	32859911
AllCCS	[M-H]-	172.5	32859911
AllCCS	[M+Na-2H]-	172.6	32859911
AllCCS	[M+HCOO]-	172.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bisbynin	CC1OCC2=C(C(O)C3OC3(CC=C(C)C)C2O)C1O	3491.3	Standard polar	33892256
Bisbynin	CC1OCC2=C(C(O)C3OC3(CC=C(C)C)C2O)C1O	2221.1	Standard non polar	33892256
Bisbynin	CC1OCC2=C(C(O)C3OC3(CC=C(C)C)C2O)C1O	2257.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bisbynin,1TMS,isomer #1	CC(C)=CCC12OC1C(O[Si](C)(C)C)C1=C(COC(C)C1O)C2O	2238.3	Semi standard non polar	33892256
Bisbynin,1TMS,isomer #2	CC(C)=CCC12OC1C(O)C1=C(COC(C)C1O)C2O[Si](C)(C)C	2266.5	Semi standard non polar	33892256
Bisbynin,1TMS,isomer #3	CC(C)=CCC12OC1C(O)C1=C(COC(C)C1O[Si](C)(C)C)C2O	2256.0	Semi standard non polar	33892256
Bisbynin,2TMS,isomer #1	CC(C)=CCC12OC1C(O[Si](C)(C)C)C1=C(COC(C)C1O[Si](C)(C)C)C2O	2260.2	Semi standard non polar	33892256
Bisbynin,2TMS,isomer #2	CC(C)=CCC12OC1C(O[Si](C)(C)C)C1=C(COC(C)C1O)C2O[Si](C)(C)C	2279.9	Semi standard non polar	33892256
Bisbynin,2TMS,isomer #3	CC(C)=CCC12OC1C(O)C1=C(COC(C)C1O[Si](C)(C)C)C2O[Si](C)(C)C	2275.4	Semi standard non polar	33892256
Bisbynin,3TMS,isomer #1	CC(C)=CCC12OC1C(O[Si](C)(C)C)C1=C(COC(C)C1O[Si](C)(C)C)C2O[Si](C)(C)C	2310.3	Semi standard non polar	33892256
Bisbynin,1TBDMS,isomer #1	CC(C)=CCC12OC1C(O[Si](C)(C)C(C)(C)C)C1=C(COC(C)C1O)C2O	2467.2	Semi standard non polar	33892256
Bisbynin,1TBDMS,isomer #2	CC(C)=CCC12OC1C(O)C1=C(COC(C)C1O)C2O[Si](C)(C)C(C)(C)C	2509.3	Semi standard non polar	33892256
Bisbynin,1TBDMS,isomer #3	CC(C)=CCC12OC1C(O)C1=C(COC(C)C1O[Si](C)(C)C(C)(C)C)C2O	2494.7	Semi standard non polar	33892256
Bisbynin,2TBDMS,isomer #1	CC(C)=CCC12OC1C(O[Si](C)(C)C(C)(C)C)C1=C(COC(C)C1O[Si](C)(C)C(C)(C)C)C2O	2683.7	Semi standard non polar	33892256
Bisbynin,2TBDMS,isomer #2	CC(C)=CCC12OC1C(O[Si](C)(C)C(C)(C)C)C1=C(COC(C)C1O)C2O[Si](C)(C)C(C)(C)C	2705.9	Semi standard non polar	33892256
Bisbynin,2TBDMS,isomer #3	CC(C)=CCC12OC1C(O)C1=C(COC(C)C1O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C	2710.3	Semi standard non polar	33892256
Bisbynin,3TBDMS,isomer #1	CC(C)=CCC12OC1C(O[Si](C)(C)C(C)(C)C)C1=C(COC(C)C1O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C	2930.5	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 - Bisbynin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fr6-7890000000-e21e3a75877413ee366e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisbynin GC-MS (3 TMS) - 70eV, Positive	splash10-005i-9132700000-5a29a79ee030a2827978	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisbynin 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 10V, Positive-QTOF	splash10-001i-1090000000-dba9bcb4ecd3c3da5eea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 20V, Positive-QTOF	splash10-066r-7090000000-489ffd8f24215d9ada8d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 40V, Positive-QTOF	splash10-0a4i-9110000000-29b71f48f10d2d118d74	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 10V, Negative-QTOF	splash10-001i-0090000000-e91a6711eb30d92ca45a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 20V, Negative-QTOF	splash10-01q9-0290000000-105da9e8ec0d8b7f202e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 40V, Negative-QTOF	splash10-014j-2930000000-6fec0372fad54c681964	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 10V, Positive-QTOF	splash10-001i-0090000000-39382db646a7b40cef58	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 20V, Positive-QTOF	splash10-0159-3590000000-ee3b22bf45c195adca1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 40V, Positive-QTOF	splash10-0006-9120000000-0d9655724f86674e8060	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 10V, Negative-QTOF	splash10-001i-0090000000-4206ab54dd729eeefe27	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 20V, Negative-QTOF	splash10-001i-0190000000-233651cb991d1b1faf18	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisbynin 40V, Negative-QTOF	splash10-03di-1490000000-87985cb95fdba12c6a2d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB021244

KNApSAcK ID

Not Available

Chemspider ID

35015154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85503029

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1891391

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 Bisbynin (HMDB0041324)

MOL for HMDB0041324 (Bisbynin)

3D MOL for HMDB0041324 (Bisbynin)

3D SDF for HMDB0041324 (Bisbynin)

3D-SDF for HMDB0041324 (Bisbynin)

PDB for HMDB0041324 (Bisbynin)

3D PDB for HMDB0041324 (Bisbynin)

SMILES for HMDB0041324 (Bisbynin)

INCHI for HMDB0041324 (Bisbynin)

Structure for HMDB0041324 (Bisbynin)

3D Structure for HMDB0041324 (Bisbynin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra