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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:32 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030394

Secondary Accession Numbers

HMDB30394

Metabolite Identification

Common Name

Simmondsin

Description

Simmondsin is found in coffee and coffee products. Simmondsin is a constituent of Simmondsia chinensis (jojoba) Simmondsin is an extract of jojoba seeds (pronounced "ho-HO-bah") (Simmondsia chinensis), it was traditionally thought to be a toxic substance due to jojoba seed meal causing weight loss in animals, but recently it has been researched as a potential treatment for reducing appetite of obese individuals by helping to reduce craving for food. Several mechanisms of action are thought to be involved in the appetite suppressant effect

Structure

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


  Mrv0541 05061305122D          

 26 27  0  0  0  0            999 V2000
    0.7145    1.2375    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    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
    2.1434    3.7125    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
    0.7145    6.1875    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
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    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
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  3  0  0  0  0
 18  6  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23  1  1  0  0  0  0
 23  9  1  0  0  0  0
 24  2  1  0  0  0  0
 24 15  1  0  0  0  0
 25  8  1  0  0  0  0
 25 16  1  0  0  0  0
 26 10  1  0  0  0  0
 26 16  1  0  0  0  0
M  END

HMDB0030394
     RDKit          3D
Simmondsin
 51 52  0  0  0  0  0  0  0  0999 V2000
    3.9738    0.7024   -2.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    1.4514   -1.7428 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7107    0.7125   -0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399    1.1464   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829   -0.1149   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725    0.1169    0.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8003   -0.4914   -0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937    0.5095   -1.2582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020    0.8541   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7050    1.6344    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830    2.8224    0.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5981   -0.3571   -0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7745   -0.7510   -2.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0094   -1.4997    0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6445   -1.5120    1.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5277   -1.4824    0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166   -1.4037    1.5198 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787   -0.7915    0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9531   -2.0471    0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6702   -2.7541    1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -3.3196    2.7589 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3675   -0.1312    1.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506    0.6450    2.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2449    0.7325    0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5445    0.2151    0.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4822    1.1387    0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5397    1.2936   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945    0.2771   -3.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5173   -0.1797   -2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571   -0.3634   -1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9637    1.5542   -1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863    1.8744    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897   -0.7507   -1.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359   -1.0152   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1875    1.5367   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2138    1.1508    1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7325    1.9067    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4686    3.1007    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6175   -0.1049   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6660   -0.5774   -2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3952   -2.4437   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4655   -2.3504    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716   -2.5231   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3265   -2.2724    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633   -2.5826    0.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831   -0.9142    1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2135    1.5758    2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2488    1.7757    0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4715    0.6416    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4166    2.0612    0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756    1.3037    2.0513 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  3  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 24  3  1  0
 16  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
M  END


  Mrv0541 05061305122D          

 26 27  0  0  0  0            999 V2000
    0.7145    1.2375    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    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
    2.1434    3.7125    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
    0.7145    6.1875    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
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    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
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  3  0  0  0  0
 18  6  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23  1  1  0  0  0  0
 23  9  1  0  0  0  0
 24  2  1  0  0  0  0
 24 15  1  0  0  0  0
 25  8  1  0  0  0  0
 25 16  1  0  0  0  0
 26 10  1  0  0  0  0
 26 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030394

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1CC(OC2OC(CO)C(O)C(O)C2O)\C(=C\C#N)C(O)C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3-

> <INCHI_KEY>
KURSRHBVYUACKS-CLTKARDFSA-N

> <FORMULA>
C16H25NO9

> <MOLECULAR_WEIGHT>
375.371

> <EXACT_MASS>
375.152931403

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
36.333325939909805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1E)-2-hydroxy-3,4-dimethoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

> <ALOGPS_LOGP>
-1.30

> <JCHEM_LOGP>
-2.9112668076666663

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.012196483340826

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.182450926739444

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083684476567

> <JCHEM_POLAR_SURFACE_AREA>
161.85999999999999

> <JCHEM_REFRACTIVITY>
85.85310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1E)-2-hydroxy-3,4-dimethoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030394
     RDKit          3D
Simmondsin
 51 52  0  0  0  0  0  0  0  0999 V2000
    3.9738    0.7024   -2.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    1.4514   -1.7428 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7107    0.7125   -0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399    1.1464   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829   -0.1149   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725    0.1169    0.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8003   -0.4914   -0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937    0.5095   -1.2582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020    0.8541   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7050    1.6344    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830    2.8224    0.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5981   -0.3571   -0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7745   -0.7510   -2.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0094   -1.4997    0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6445   -1.5120    1.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5277   -1.4824    0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166   -1.4037    1.5198 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787   -0.7915    0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9531   -2.0471    0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6702   -2.7541    1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -3.3196    2.7589 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3675   -0.1312    1.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506    0.6450    2.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2449    0.7325    0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5445    0.2151    0.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4822    1.1387    0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5397    1.2936   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945    0.2771   -3.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5173   -0.1797   -2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571   -0.3634   -1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9637    1.5542   -1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863    1.8744    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897   -0.7507   -1.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359   -1.0152   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1875    1.5367   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2138    1.1508    1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7325    1.9067    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4686    3.1007    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6175   -0.1049   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6660   -0.5774   -2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3952   -2.4437   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4655   -2.3504    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716   -2.5231   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3265   -2.2724    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633   -2.5826    0.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831   -0.9142    1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2135    1.5758    2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2488    1.7757    0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4715    0.6416    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4166    2.0612    0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756    1.3037    2.0513 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  3  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 24  3  1  0
 16  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       9.336   5.390   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       0.000  13.860   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3    4    7                                                       
CONECT    4    3   17                                                       
CONECT    5    8    9                                                       
CONECT    6   10   18                                                       
CONECT    7    3    8   11                                                  
CONECT    8    5    7   25                                                  
CONECT    9    5   15   23                                                  
CONECT   10    6   12   26                                                  
CONECT   11    7   15   19                                                  
CONECT   12   10   13   20                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   16   22                                                  
CONECT   15    9   11   24                                                  
CONECT   16   14   25   26                                                  
CONECT   17    4                                                            
CONECT   18    6                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23    1    9                                                       
CONECT   24    2   15                                                       
CONECT   25    8   16                                                       
CONECT   26   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0030394
HETATM    1  C1  UNL     1       3.974   0.702  -2.776  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.421   1.451  -1.743  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.711   0.713  -0.846  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.240   1.146  -0.762  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.483  -0.115  -0.401  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.772   0.117   0.089  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.800  -0.491  -0.670  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.494   0.509  -1.258  1.00  0.00           O  
HETATM    9  C6  UNL     1      -3.702   0.854  -0.779  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.705   1.634   0.506  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.983   2.822   0.249  1.00  0.00           O  
HETATM   12  C8  UNL     1      -4.598  -0.357  -0.741  1.00  0.00           C  
HETATM   13  O5  UNL     1      -4.774  -0.751  -2.077  1.00  0.00           O  
HETATM   14  C9  UNL     1      -4.009  -1.500   0.017  1.00  0.00           C  
HETATM   15  O6  UNL     1      -4.645  -1.512   1.283  1.00  0.00           O  
HETATM   16  C10 UNL     1      -2.528  -1.482   0.140  1.00  0.00           C  
HETATM   17  O7  UNL     1      -2.217  -1.404   1.520  1.00  0.00           O  
HETATM   18  C11 UNL     1       1.279  -0.791   0.670  1.00  0.00           C  
HETATM   19  C12 UNL     1       0.953  -2.047   0.932  1.00  0.00           C  
HETATM   20  C13 UNL     1       1.670  -2.754   1.942  1.00  0.00           C  
HETATM   21  N1  UNL     1       2.267  -3.320   2.759  1.00  0.00           N  
HETATM   22  C14 UNL     1       2.367  -0.131   1.411  1.00  0.00           C  
HETATM   23  O8  UNL     1       1.851   0.645   2.472  1.00  0.00           O  
HETATM   24  C15 UNL     1       3.245   0.733   0.551  1.00  0.00           C  
HETATM   25  O9  UNL     1       4.545   0.215   0.513  1.00  0.00           O  
HETATM   26  C16 UNL     1       5.482   1.139   0.964  1.00  0.00           C  
HETATM   27  H1  UNL     1       4.540   1.294  -3.491  1.00  0.00           H  
HETATM   28  H2  UNL     1       3.094   0.277  -3.342  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.517  -0.180  -2.379  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.757  -0.363  -1.188  1.00  0.00           H  
HETATM   31  H5  UNL     1       0.964   1.554  -1.737  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.086   1.874   0.046  1.00  0.00           H  
HETATM   33  H7  UNL     1       0.490  -0.751  -1.326  1.00  0.00           H  
HETATM   34  H8  UNL     1      -1.236  -1.015  -1.501  1.00  0.00           H  
HETATM   35  H9  UNL     1      -4.188   1.537  -1.543  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.214   1.151   1.343  1.00  0.00           H  
HETATM   37  H11 UNL     1      -4.733   1.907   0.760  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.469   3.101   1.040  1.00  0.00           H  
HETATM   39  H13 UNL     1      -5.617  -0.105  -0.361  1.00  0.00           H  
HETATM   40  H14 UNL     1      -5.666  -0.577  -2.416  1.00  0.00           H  
HETATM   41  H15 UNL     1      -4.395  -2.444  -0.474  1.00  0.00           H  
HETATM   42  H16 UNL     1      -4.466  -2.350   1.766  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.172  -2.523  -0.131  1.00  0.00           H  
HETATM   44  H18 UNL     1      -2.326  -2.272   1.960  1.00  0.00           H  
HETATM   45  H19 UNL     1       0.163  -2.583   0.421  1.00  0.00           H  
HETATM   46  H20 UNL     1       2.983  -0.914   1.899  1.00  0.00           H  
HETATM   47  H21 UNL     1       2.213   1.576   2.425  1.00  0.00           H  
HETATM   48  H22 UNL     1       3.249   1.776   0.937  1.00  0.00           H  
HETATM   49  H23 UNL     1       6.472   0.642   0.897  1.00  0.00           H  
HETATM   50  H24 UNL     1       5.417   2.061   0.378  1.00  0.00           H  
HETATM   51  H25 UNL     1       5.276   1.304   2.051  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4   24   30
CONECT    4    5   31   32
CONECT    5    6   18   33
CONECT    6    7
CONECT    7    8   16   34
CONECT    8    9
CONECT    9   10   12   35
CONECT   10   11   36   37
CONECT   11   38
CONECT   12   13   14   39
CONECT   13   40
CONECT   14   15   16   41
CONECT   15   42
CONECT   16   17   43
CONECT   17   44
CONECT   18   19   19   22
CONECT   19   20   45
CONECT   20   21   21   21
CONECT   22   23   24   46
CONECT   23   47
CONECT   24   25   48
CONECT   25   26
CONECT   26   49   50   51
END

HMDB0030394
     RDKit          3D
Simmondsin
 51 52  0  0  0  0  0  0  0  0999 V2000
    3.9738    0.7024   -2.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    1.4514   -1.7428 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7107    0.7125   -0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399    1.1464   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829   -0.1149   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725    0.1169    0.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8003   -0.4914   -0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937    0.5095   -1.2582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020    0.8541   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7050    1.6344    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830    2.8224    0.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5981   -0.3571   -0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7745   -0.7510   -2.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0094   -1.4997    0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6445   -1.5120    1.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5277   -1.4824    0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166   -1.4037    1.5198 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787   -0.7915    0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9531   -2.0471    0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6702   -2.7541    1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -3.3196    2.7589 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3675   -0.1312    1.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506    0.6450    2.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2449    0.7325    0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5445    0.2151    0.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4822    1.1387    0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5397    1.2936   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945    0.2771   -3.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5173   -0.1797   -2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571   -0.3634   -1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9637    1.5542   -1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863    1.8744    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897   -0.7507   -1.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2359   -1.0152   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1875    1.5367   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2138    1.1508    1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7325    1.9067    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4686    3.1007    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6175   -0.1049   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6660   -0.5774   -2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3952   -2.4437   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4655   -2.3504    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716   -2.5231   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3265   -2.2724    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633   -2.5826    0.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831   -0.9142    1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2135    1.5758    2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2488    1.7757    0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4715    0.6416    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4166    2.0612    0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756    1.3037    2.0513 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  3  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 24  3  1  0
 16  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Cyanomethylene-1-glucosyloxy-3-hydroxy-4,5-dimethoxycyclohexane	HMDB
[6-(b-D-Glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene]acetonitrile, 9ci	HMDB
2-(Cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl-beta-glucoside	HMDB
Simmondsin	MeSH

Chemical Formula

C₁₆H₂₅NO₉

Average Molecular Weight

375.371

Monoisotopic Molecular Weight

375.152931403

IUPAC Name

2-[(1E)-2-hydroxy-3,4-dimethoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

Traditional Name

2-[(1E)-2-hydroxy-3,4-dimethoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

CAS Registry Number

51771-52-9

SMILES

COC1CC(OC2OC(CO)C(O)C(O)C2O)\C(=C\C#N)C(O)C1OC

InChI Identifier

InChI=1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3-

InChI Key

KURSRHBVYUACKS-CLTKARDFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Cyclitol or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Nitrile
Carbonitrile
Oxacycle
Ether
Dialkyl ether
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Alcohol
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030394)
Cytoplasm (HMDB: HMDB0030394)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030394)

Source

Endogenous

Endogenous (HMDB: HMDB0030394)

Plant

Plant (HMDB: HMDB0030394)
Coffea (HMDB: HMDB0030394)

Exogenous

Food

Food (HMDB: HMDB0030394)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Nut

Nuts (FooDB: FOOD00869)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	95 - 100 °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	50.6 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.9	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.85 m³·mol⁻¹	ChemAxon
Polarizability	36.33 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]+	187.182	31661259
DarkChem	[M-H]-	177.839	31661259
DeepCCS	[M+H]+	186.142	30932474
DeepCCS	[M-H]-	183.272	30932474
DeepCCS	[M-2H]-	218.667	30932474
DeepCCS	[M+Na]+	194.957	30932474
AllCCS	[M+H]+	188.1	32859911
AllCCS	[M+H-H2O]+	185.5	32859911
AllCCS	[M+NH4]+	190.5	32859911
AllCCS	[M+Na]+	191.1	32859911
AllCCS	[M-H]-	186.5	32859911
AllCCS	[M+Na-2H]-	186.6	32859911
AllCCS	[M+HCOO]-	186.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Simmondsin	COC1CC(OC2OC(CO)C(O)C(O)C2O)\C(=C\C#N)C(O)C1OC	3590.3	Standard polar	33892256
Simmondsin	COC1CC(OC2OC(CO)C(O)C(O)C2O)\C(=C\C#N)C(O)C1OC	2922.7	Standard non polar	33892256
Simmondsin	COC1CC(OC2OC(CO)C(O)C(O)C2O)\C(=C\C#N)C(O)C1OC	3135.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Simmondsin,1TMS,isomer #1	COC1CC(OC2OC(CO[Si](C)(C)C)C(O)C(O)C2O)/C(=C/C#N)C(O)C1OC	3020.1	Semi standard non polar	33892256
Simmondsin,1TMS,isomer #2	COC1CC(OC2OC(CO)C(O[Si](C)(C)C)C(O)C2O)/C(=C/C#N)C(O)C1OC	3013.7	Semi standard non polar	33892256
Simmondsin,1TMS,isomer #3	COC1CC(OC2OC(CO)C(O)C(O[Si](C)(C)C)C2O)/C(=C/C#N)C(O)C1OC	3008.2	Semi standard non polar	33892256
Simmondsin,1TMS,isomer #4	COC1CC(OC2OC(CO)C(O)C(O)C2O[Si](C)(C)C)/C(=C/C#N)C(O)C1OC	3005.5	Semi standard non polar	33892256
Simmondsin,1TMS,isomer #5	COC1CC(OC2OC(CO)C(O)C(O)C2O)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	3019.4	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #1	COC1CC(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O)/C(=C/C#N)C(O)C1OC	3029.4	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #10	COC1CC(OC2OC(CO)C(O)C(O)C2O[Si](C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	3028.2	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #2	COC1CC(OC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O)/C(=C/C#N)C(O)C1OC	3022.0	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #3	COC1CC(OC2OC(CO[Si](C)(C)C)C(O)C(O)C2O[Si](C)(C)C)/C(=C/C#N)C(O)C1OC	3028.7	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #4	COC1CC(OC2OC(CO[Si](C)(C)C)C(O)C(O)C2O)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	3019.1	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #5	COC1CC(OC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)/C(=C/C#N)C(O)C1OC	3021.1	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #6	COC1CC(OC2OC(CO)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)/C(=C/C#N)C(O)C1OC	3017.3	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #7	COC1CC(OC2OC(CO)C(O[Si](C)(C)C)C(O)C2O)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	3031.6	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #8	COC1CC(OC2OC(CO)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)/C(=C/C#N)C(O)C1OC	3016.5	Semi standard non polar	33892256
Simmondsin,2TMS,isomer #9	COC1CC(OC2OC(CO)C(O)C(O[Si](C)(C)C)C2O)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	3018.4	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #1	COC1CC(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)/C(=C/C#N)C(O)C1OC	3000.1	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #10	COC1CC(OC2OC(CO)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	2985.1	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #2	COC1CC(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)/C(=C/C#N)C(O)C1OC	3001.1	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #3	COC1CC(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	3002.0	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #4	COC1CC(OC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)/C(=C/C#N)C(O)C1OC	2978.1	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #5	COC1CC(OC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	2990.5	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #6	COC1CC(OC2OC(CO[Si](C)(C)C)C(O)C(O)C2O[Si](C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	3000.8	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #7	COC1CC(OC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)/C(=C/C#N)C(O)C1OC	3001.4	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #8	COC1CC(OC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	3003.1	Semi standard non polar	33892256
Simmondsin,3TMS,isomer #9	COC1CC(OC2OC(CO)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	2996.0	Semi standard non polar	33892256
Simmondsin,4TMS,isomer #1	COC1CC(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)/C(=C/C#N)C(O)C1OC	2931.1	Semi standard non polar	33892256
Simmondsin,4TMS,isomer #2	COC1CC(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	2949.8	Semi standard non polar	33892256
Simmondsin,4TMS,isomer #3	COC1CC(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	2945.8	Semi standard non polar	33892256
Simmondsin,4TMS,isomer #4	COC1CC(OC2OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	2920.4	Semi standard non polar	33892256
Simmondsin,4TMS,isomer #5	COC1CC(OC2OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	2923.1	Semi standard non polar	33892256
Simmondsin,5TMS,isomer #1	COC1CC(OC2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C)C1OC	2865.1	Semi standard non polar	33892256
Simmondsin,1TBDMS,isomer #1	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O)/C(=C/C#N)C(O)C1OC	3255.0	Semi standard non polar	33892256
Simmondsin,1TBDMS,isomer #2	COC1CC(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)/C(=C/C#N)C(O)C1OC	3262.5	Semi standard non polar	33892256
Simmondsin,1TBDMS,isomer #3	COC1CC(OC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)/C(=C/C#N)C(O)C1OC	3258.2	Semi standard non polar	33892256
Simmondsin,1TBDMS,isomer #4	COC1CC(OC2OC(CO)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O)C1OC	3252.6	Semi standard non polar	33892256
Simmondsin,1TBDMS,isomer #5	COC1CC(OC2OC(CO)C(O)C(O)C2O)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3270.6	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #1	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)/C(=C/C#N)C(O)C1OC	3433.0	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #10	COC1CC(OC2OC(CO)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3445.3	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #2	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)/C(=C/C#N)C(O)C1OC	3440.0	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #3	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O)C1OC	3433.4	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #4	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3430.7	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #5	COC1CC(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)/C(=C/C#N)C(O)C1OC	3437.3	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #6	COC1CC(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O)C1OC	3435.3	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #7	COC1CC(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3451.3	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #8	COC1CC(OC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O)C1OC	3429.3	Semi standard non polar	33892256
Simmondsin,2TBDMS,isomer #9	COC1CC(OC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3437.1	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #1	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)/C(=C/C#N)C(O)C1OC	3585.5	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #10	COC1CC(OC2OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3571.1	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #2	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O)C1OC	3585.7	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #3	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3583.1	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #4	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O)C1OC	3572.9	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #5	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3581.9	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #6	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3586.7	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #7	COC1CC(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O)C1OC	3572.9	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #8	COC1CC(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3577.5	Semi standard non polar	33892256
Simmondsin,3TBDMS,isomer #9	COC1CC(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3576.7	Semi standard non polar	33892256
Simmondsin,4TBDMS,isomer #1	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O)C1OC	3705.8	Semi standard non polar	33892256
Simmondsin,4TBDMS,isomer #2	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3724.8	Semi standard non polar	33892256
Simmondsin,4TBDMS,isomer #3	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3711.8	Semi standard non polar	33892256
Simmondsin,4TBDMS,isomer #4	COC1CC(OC2OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3707.8	Semi standard non polar	33892256
Simmondsin,4TBDMS,isomer #5	COC1CC(OC2OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)/C(=C/C#N)C(O[Si](C)(C)C(C)(C)C)C1OC	3691.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Simmondsin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pbc-6709000000-6998950778cd28d8115f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Simmondsin GC-MS (4 TMS) - 70eV, Positive	splash10-0002-5700029000-7d5f45c590134067edbc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Simmondsin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Simmondsin 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 - Simmondsin 10V, Positive-QTOF	splash10-08i1-0859000000-75c9aa237be28bb87161	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 20V, Positive-QTOF	splash10-0002-0931000000-334b1b9ad66bce406d80	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 40V, Positive-QTOF	splash10-0f6t-9810000000-7e46d7dfb818bceb9ef2	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 10V, Negative-QTOF	splash10-0229-1549000000-f17a64c9d81a11e6b273	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 20V, Negative-QTOF	splash10-03dj-2942000000-754398f69da1c15e0816	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 40V, Negative-QTOF	splash10-0295-5930000000-dc664cfc0e9ff444576b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 10V, Positive-QTOF	splash10-004i-0119000000-d8c528e451fd3e295a78	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 20V, Positive-QTOF	splash10-03dj-0933000000-3b292e8d59637d682a1d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 40V, Positive-QTOF	splash10-08fr-7690000000-c0bd49d4c6ff3a7fbb04	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 10V, Negative-QTOF	splash10-00di-0019000000-a564b8e7ffa695a32dd3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 20V, Negative-QTOF	splash10-0c00-3879000000-f826e8fc4fa488e85bb0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Simmondsin 40V, Negative-QTOF	splash10-052b-8941000000-de6b200cc3b38374a3e6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

FDB002248

KNApSAcK ID

C00054414

Chemspider ID

4733931

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Simmondsin

METLIN ID

Not Available

PubChem Compound

5884740

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

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

Showing metabocard for Simmondsin (HMDB0030394)

MOL for HMDB0030394 (Simmondsin)

3D MOL for HMDB0030394 (Simmondsin)

3D SDF for HMDB0030394 (Simmondsin)

3D-SDF for HMDB0030394 (Simmondsin)

PDB for HMDB0030394 (Simmondsin)

3D PDB for HMDB0030394 (Simmondsin)

SMILES for HMDB0030394 (Simmondsin)

INCHI for HMDB0030394 (Simmondsin)

Structure for HMDB0030394 (Simmondsin)

3D Structure for HMDB0030394 (Simmondsin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra