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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:44:41 UTC

Update Date

2022-03-07 02:54:58 UTC

HMDB ID

HMDB0036587

Secondary Accession Numbers

HMDB36587

Metabolite Identification

Common Name

Quassin

Description

Quassin belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Based on a literature review a small amount of articles have been published on Quassin.

Structure

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


  Mrv0541 05061309132D          

 28 31  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    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
    3.5724    1.2375    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
   -0.7145    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
    0.0000    3.3000    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
    0.0000    2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 10  7  1  0  0  0  0
 11  2  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 18 11  2  0  0  0  0
 18 17  1  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21  3  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22 12  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  2  0  0  0  0
 25 20  2  0  0  0  0
 26  5  1  0  0  0  0
 26 14  1  0  0  0  0
 27  6  1  0  0  0  0
 27 18  1  0  0  0  0
 28 15  1  0  0  0  0
 28 16  1  0  0  0  0
M  END

HMDB0036587
     RDKit          3D
Quassin
 56 59  0  0  0  0  0  0  0  0999 V2000
    4.3731    3.1579   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    2.5978    0.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    1.3796    0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539    0.2802    1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -1.0461    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -1.8236    0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221   -0.9221    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967   -2.2218    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884   -2.1096   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500   -2.1614    1.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6251   -2.1452    1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2769   -2.5372    2.3538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369   -1.6339    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5841   -0.6029   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9854    0.6932   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557    1.1022   -0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1390    1.5351    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546    2.7863    0.9686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9809    2.8881    2.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7406    1.1514    0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092    1.5436    1.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    0.3021   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.0680   -0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145   -0.3123   -1.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    1.3578   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3022    2.4076   -0.6660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515   -0.9026   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9924   -1.3533   -2.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1712    2.4777   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8316    4.1143    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    3.3180   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355    0.3024    1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8857   -1.5962    1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736   -2.7290   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1781   -1.1909   -0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6091   -2.1865    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426   -0.5822    1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9836   -2.9289    0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653   -2.7271   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0193   -3.0295   -0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -2.5096   -0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3023   -1.2037    0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1482   -0.6575   -1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8507    0.6291   -1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9862    0.7038    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5088    2.1858   -0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2487    3.9518    2.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182    2.3091    2.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999    2.5999    3.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965    0.8921   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719    0.2642   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1110   -1.3534   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1504    0.0205   -2.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1534   -0.5299   -2.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879   -2.0321   -2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -1.9911   -2.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 22 27  1  0
 27 28  1  0
 25  3  1  0
 23  7  1  0
 27  9  1  0
 27 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
M  END


  Mrv0541 05061309132D          

 28 31  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    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
    3.5724    1.2375    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
   -0.7145    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
    0.0000    3.3000    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
    0.0000    2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 10  7  1  0  0  0  0
 11  2  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 18 11  2  0  0  0  0
 18 17  1  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21  3  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22 12  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  2  0  0  0  0
 25 20  2  0  0  0  0
 26  5  1  0  0  0  0
 26 14  1  0  0  0  0
 27  6  1  0  0  0  0
 27 18  1  0  0  0  0
 28 15  1  0  0  0  0
 28 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036587

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3

> <INCHI_KEY>
IOSXSVZRTUWBHC-UHFFFAOYSA-N

> <FORMULA>
C22H28O6

> <MOLECULAR_WEIGHT>
388.4541

> <EXACT_MASS>
388.188588628

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.99780541870241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,15-dimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.235244382666666

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.076212391719164

> <JCHEM_PKA_STRONGEST_BASIC>
-4.595373576144004

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
104.20339999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quassin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036587
     RDKit          3D
Quassin
 56 59  0  0  0  0  0  0  0  0999 V2000
    4.3731    3.1579   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    2.5978    0.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    1.3796    0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539    0.2802    1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -1.0461    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -1.8236    0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221   -0.9221    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967   -2.2218    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884   -2.1096   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500   -2.1614    1.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6251   -2.1452    1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2769   -2.5372    2.3538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369   -1.6339    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5841   -0.6029   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9854    0.6932   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557    1.1022   -0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1390    1.5351    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546    2.7863    0.9686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9809    2.8881    2.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7406    1.1514    0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092    1.5436    1.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    0.3021   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.0680   -0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145   -0.3123   -1.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    1.3578   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3022    2.4076   -0.6660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515   -0.9026   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9924   -1.3533   -2.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1712    2.4777   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8316    4.1143    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    3.3180   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355    0.3024    1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8857   -1.5962    1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736   -2.7290   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1781   -1.1909   -0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6091   -2.1865    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426   -0.5822    1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9836   -2.9289    0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653   -2.7271   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0193   -3.0295   -0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -2.5096   -0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3023   -1.2037    0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1482   -0.6575   -1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8507    0.6291   -1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9862    0.7038    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5088    2.1858   -0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2487    3.9518    2.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182    2.3091    2.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999    2.5999    3.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965    0.8921   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719    0.2642   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1110   -1.3534   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1504    0.0205   -2.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1534   -0.5299   -2.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879   -2.0321   -2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -1.9911   -2.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 22 27  1  0
 27 28  1  0
 25  3  1  0
 23  7  1  0
 27  9  1  0
 27 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   26                                                            
CONECT    6   27                                                            
CONECT    7   10   14                                                       
CONECT    8   12   15                                                       
CONECT    9   13   16                                                       
CONECT   10    1    7   12                                                  
CONECT   11    2   13   18                                                  
CONECT   12    8   10   22                                                  
CONECT   13    9   11   21                                                  
CONECT   14    7   20   26                                                  
CONECT   15    8   21   28                                                  
CONECT   16    9   23   28                                                  
CONECT   17   18   19   24                                                  
CONECT   18   11   17   27                                                  
CONECT   19   17   21   22                                                  
CONECT   20   14   22   25                                                  
CONECT   21    3   13   15   19                                             
CONECT   22    4   12   19   20                                             
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   20                                                            
CONECT   26    5   14                                                       
CONECT   27    6   18                                                       
CONECT   28   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0036587
HETATM    1  C1  UNL     1       4.373   3.158  -0.069  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.614   2.598   0.987  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.964   1.380   0.675  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.454   0.280   1.208  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.849  -1.046   0.947  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.726  -1.824   0.011  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.422  -0.922   0.515  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.797  -2.222   0.122  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.688  -2.110  -0.033  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.250  -2.161   1.259  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.625  -2.145   1.351  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.277  -2.537   2.354  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.337  -1.634   0.193  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.584  -0.603  -0.631  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.985   0.693  -0.080  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.456   1.102  -0.107  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.139   1.535   0.440  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.555   2.786   0.969  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.981   2.888   2.313  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.741   1.151   0.463  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.009   1.544   1.406  1.00  0.00           O  
HETATM   22  C17 UNL     1      -0.298   0.302  -0.673  1.00  0.00           C  
HETATM   23  C18 UNL     1       1.189   0.068  -0.563  1.00  0.00           C  
HETATM   24  C19 UNL     1       1.815  -0.312  -1.883  1.00  0.00           C  
HETATM   25  C20 UNL     1       1.812   1.358  -0.194  1.00  0.00           C  
HETATM   26  O6  UNL     1       1.302   2.408  -0.666  1.00  0.00           O  
HETATM   27  C21 UNL     1      -1.152  -0.903  -0.817  1.00  0.00           C  
HETATM   28  C22 UNL     1      -0.992  -1.353  -2.291  1.00  0.00           C  
HETATM   29  H1  UNL     1       5.171   2.478  -0.401  1.00  0.00           H  
HETATM   30  H2  UNL     1       4.832   4.114   0.196  1.00  0.00           H  
HETATM   31  H3  UNL     1       3.705   3.318  -0.956  1.00  0.00           H  
HETATM   32  H4  UNL     1       4.335   0.302   1.871  1.00  0.00           H  
HETATM   33  H5  UNL     1       2.886  -1.596   1.936  1.00  0.00           H  
HETATM   34  H6  UNL     1       3.274  -2.729  -0.398  1.00  0.00           H  
HETATM   35  H7  UNL     1       4.178  -1.191  -0.782  1.00  0.00           H  
HETATM   36  H8  UNL     1       4.609  -2.186   0.619  1.00  0.00           H  
HETATM   37  H9  UNL     1       0.843  -0.582   1.423  1.00  0.00           H  
HETATM   38  H10 UNL     1       0.984  -2.929   0.987  1.00  0.00           H  
HETATM   39  H11 UNL     1       1.265  -2.727  -0.744  1.00  0.00           H  
HETATM   40  H12 UNL     1      -1.019  -3.029  -0.560  1.00  0.00           H  
HETATM   41  H13 UNL     1      -3.613  -2.510  -0.443  1.00  0.00           H  
HETATM   42  H14 UNL     1      -4.302  -1.204   0.526  1.00  0.00           H  
HETATM   43  H15 UNL     1      -3.148  -0.657  -1.626  1.00  0.00           H  
HETATM   44  H16 UNL     1      -4.851   0.629  -1.029  1.00  0.00           H  
HETATM   45  H17 UNL     1      -4.986   0.704   0.762  1.00  0.00           H  
HETATM   46  H18 UNL     1      -4.509   2.186  -0.241  1.00  0.00           H  
HETATM   47  H19 UNL     1      -3.249   3.952   2.479  1.00  0.00           H  
HETATM   48  H20 UNL     1      -3.918   2.309   2.403  1.00  0.00           H  
HETATM   49  H21 UNL     1      -2.200   2.600   3.029  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.397   0.892  -1.638  1.00  0.00           H  
HETATM   51  H23 UNL     1       2.772   0.264  -2.070  1.00  0.00           H  
HETATM   52  H24 UNL     1       2.111  -1.353  -1.977  1.00  0.00           H  
HETATM   53  H25 UNL     1       1.150   0.021  -2.700  1.00  0.00           H  
HETATM   54  H26 UNL     1      -1.153  -0.530  -2.985  1.00  0.00           H  
HETATM   55  H27 UNL     1      -1.888  -2.032  -2.443  1.00  0.00           H  
HETATM   56  H28 UNL     1      -0.130  -1.991  -2.445  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   32
CONECT    5    6    7   33
CONECT    6   34   35   36
CONECT    7    8   23   37
CONECT    8    9   38   39
CONECT    9   10   27   40
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   41   42
CONECT   14   15   27   43
CONECT   15   16   17   17
CONECT   16   44   45   46
CONECT   17   18   20
CONECT   18   19
CONECT   19   47   48   49
CONECT   20   21   21   22
CONECT   22   23   27   50
CONECT   23   24   25
CONECT   24   51   52   53
CONECT   25   26   26
CONECT   27   28
CONECT   28   54   55   56
END

HMDB0036587
     RDKit          3D
Quassin
 56 59  0  0  0  0  0  0  0  0999 V2000
    4.3731    3.1579   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    2.5978    0.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    1.3796    0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539    0.2802    1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -1.0461    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -1.8236    0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221   -0.9221    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967   -2.2218    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884   -2.1096   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500   -2.1614    1.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6251   -2.1452    1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2769   -2.5372    2.3538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369   -1.6339    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5841   -0.6029   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9854    0.6932   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557    1.1022   -0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1390    1.5351    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5546    2.7863    0.9686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9809    2.8881    2.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7406    1.1514    0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092    1.5436    1.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    0.3021   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.0680   -0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145   -0.3123   -1.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    1.3578   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3022    2.4076   -0.6660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515   -0.9026   -0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9924   -1.3533   -2.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1712    2.4777   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8316    4.1143    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    3.3180   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3355    0.3024    1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8857   -1.5962    1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736   -2.7290   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1781   -1.1909   -0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6091   -2.1865    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426   -0.5822    1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9836   -2.9289    0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653   -2.7271   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0193   -3.0295   -0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -2.5096   -0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3023   -1.2037    0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1482   -0.6575   -1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8507    0.6291   -1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9862    0.7038    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5088    2.1858   -0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2487    3.9518    2.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182    2.3091    2.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999    2.5999    3.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965    0.8921   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719    0.2642   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1110   -1.3534   -1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1504    0.0205   -2.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1534   -0.5299   -2.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879   -2.0321   -2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -1.9911   -2.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 22 27  1  0
 27 28  1  0
 25  3  1  0
 23  7  1  0
 27  9  1  0
 27 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Nigakilactone D	HMDB
Quassin	MeSH

Chemical Formula

C₂₂H₂₈O₆

Average Molecular Weight

388.4541

Monoisotopic Molecular Weight

388.188588628

IUPAC Name

4,15-dimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione

Traditional Name

quassin

CAS Registry Number

76-78-8

SMILES

COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O

InChI Identifier

InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3

InChI Key

IOSXSVZRTUWBHC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Delta valerolactone
Cyclohexenone
Delta_valerolactone
Pyran
Oxane
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	221 - 222 °C	Not Available
Boiling Point	586.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	566.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.220 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.043 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.24	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.08	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.2 m³·mol⁻¹	ChemAxon
Polarizability	41 Å³	ChemAxon
Number of Rings	4	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]+	192.024	31661259
DarkChem	[M-H]-	186.721	31661259
DeepCCS	[M-2H]-	228.907	30932474
DeepCCS	[M+Na]+	204.432	30932474
AllCCS	[M+H]+	190.7	32859911
AllCCS	[M+H-H2O]+	188.2	32859911
AllCCS	[M+NH4]+	193.0	32859911
AllCCS	[M+Na]+	193.7	32859911
AllCCS	[M-H]-	197.9	32859911
AllCCS	[M+Na-2H]-	198.4	32859911
AllCCS	[M+HCOO]-	199.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.39 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4494 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.66 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2977.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	250.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	592.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	581.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1120.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	534.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1536.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	214.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	13.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quassin	COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O	3953.9	Standard polar	33892256
Quassin	COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O	2706.1	Standard non polar	33892256
Quassin	COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O	3037.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quassin,1TMS,isomer #1	COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(O[Si](C)(C)C)=C(C2(C)C1=O)C34C	2949.0	Semi standard non polar	33892256
Quassin,1TMS,isomer #1	COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(O[Si](C)(C)C)=C(C2(C)C1=O)C34C	2761.5	Standard non polar	33892256
Quassin,1TBDMS,isomer #1	COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C(C2(C)C1=O)C34C	3161.1	Semi standard non polar	33892256
Quassin,1TBDMS,isomer #1	COC1=CC(C)C2CC3OC(=O)CC4C(C)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C(C2(C)C1=O)C34C	2979.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Quassin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0odj-0209000000-e284c8786161fb2c0379	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quassin 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 - Quassin 10V, Positive-QTOF	splash10-000i-0009000000-7e540d032cd53e8bed92	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 20V, Positive-QTOF	splash10-0072-0019000000-17bae020877053ca3160	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 40V, Positive-QTOF	splash10-0udi-9453000000-d49be7bcb435b4da0085	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 10V, Negative-QTOF	splash10-000i-0009000000-9ac13bf543d17c7a8ccd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 20V, Negative-QTOF	splash10-000l-0009000000-ac85f55d6c57b2e68200	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 40V, Negative-QTOF	splash10-002f-3019000000-c8ca587aaf4c7a602155	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 10V, Positive-QTOF	splash10-000l-0009000000-7da52e89cb542bda89c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 20V, Positive-QTOF	splash10-03dr-0029000000-a48b2bc4a57e0ce12130	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 40V, Positive-QTOF	splash10-00n0-3897000000-6f3942b0306db2d2d125	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 10V, Negative-QTOF	splash10-000i-0009000000-7f16ac45973a6479b3e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 20V, Negative-QTOF	splash10-000i-0009000000-f8847d5c1dba461f6dac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quassin 40V, Negative-QTOF	splash10-0avr-0029000000-d98d24d4098095349f75	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Quassin

METLIN ID

Not Available

PubChem Compound

4998

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1368861

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Quassin (HMDB0036587)

MOL for HMDB0036587 (Quassin)

3D MOL for HMDB0036587 (Quassin)

3D SDF for HMDB0036587 (Quassin)

3D-SDF for HMDB0036587 (Quassin)

PDB for HMDB0036587 (Quassin)

3D PDB for HMDB0036587 (Quassin)

SMILES for HMDB0036587 (Quassin)

INCHI for HMDB0036587 (Quassin)

Structure for HMDB0036587 (Quassin)

3D Structure for HMDB0036587 (Quassin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra