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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:07:51 UTC

Update Date

2022-03-07 02:55:07 UTC

HMDB ID

HMDB0036941

Secondary Accession Numbers

HMDB36941

Metabolite Identification

Common Name

Smilagenone

Description

Smilagenone, also known as sarsasapogenone or spirostan-3-one, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Smilagenone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 02241217592D          

 30 35  0  0  0  0            999 V2000
   -2.0281   -0.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -1.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7432   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -1.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -1.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7432   -2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -1.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145   -2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995   -1.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995   -1.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145    0.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995    0.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141    0.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    0.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993   -0.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846   -0.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684    0.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684    0.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9220    0.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5035    1.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1718    2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993    0.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846    1.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289    1.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7501    2.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    1.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718   -2.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 30  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 25  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 25  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 26  1  0  0  0  0
 20 29  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 28  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0036941
     RDKit          3D
Smilagenone
 72 77  0  0  0  0  0  0  0  0999 V2000
    7.0458   -0.3835   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -0.7076    1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857   -1.6599    0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697   -1.2224    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604    0.1397    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510    0.9665    0.6688 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3474    0.5528    1.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807    0.6212    1.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5202    1.5320    0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289    1.5744    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425    1.5355   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0016    1.2345   -0.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    2.0577    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1667    1.8499    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6168    0.5487   -0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9898    0.2533    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4732   -1.1077    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6019   -1.3771   -0.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4920   -2.2217    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1761   -1.8212   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6143   -0.5476    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071   -0.8250    1.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544   -0.2062   -0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2696   -1.1395   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0947   -0.8214   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151    0.5194   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    0.4781   -2.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    1.0670   -0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405    0.0155   -0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8512    0.3907   -1.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0132   -0.8507    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1681    0.7112   -0.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7316   -0.7978   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585   -1.1463    1.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8814   -1.7130   -0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1645   -2.7037    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6556   -1.2249    2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8765   -1.9381    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1225    1.3483    1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9979    0.4403    2.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    2.5410    0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3139    0.7938    1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    2.5644    1.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161    2.5269   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420    1.7235   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819    1.9818    1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317    3.1383    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265    2.6592   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382    1.9139    1.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876    0.6599   -1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6904    0.9648   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1028    0.4662    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -3.1386   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906   -2.4650    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2670   -1.7306   -1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702   -2.6682   -0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -1.9196    1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -0.2750    2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3754   -0.5824    2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5873   -0.4961   -1.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233   -1.3020    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5317   -2.1603   -0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920   -0.9171    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -1.5803   -1.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2929   -0.5433   -3.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9408    0.7372   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    1.2229   -3.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274    1.8943   -1.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203   -1.0042   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -0.4612   -2.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7013    0.8446   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874    1.1899   -2.4920 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
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
  7  2  1  0
 28  9  1  0
 29  5  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  0
 29 69  1  0
 30 70  1  0
 30 71  1  0
 30 72  1  0
M  END


  Mrv0541 02241217592D          

 30 35  0  0  0  0            999 V2000
   -2.0281   -0.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -1.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7432   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -1.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -1.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7432   -2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -1.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145   -2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995   -1.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995   -1.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3145    0.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5995    0.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141    0.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    0.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993   -0.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846   -0.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684    0.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684    0.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9220    0.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5035    1.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1718    2.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993    0.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846    1.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289    1.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7501    2.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    1.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718   -2.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 30  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 25  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 25  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 26  1  0  0  0  0
 20 29  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 28  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036941

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(CC3C4CCC5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-18,20-24H,5-15H2,1-4H3

> <INCHI_KEY>
CIBAPVLFORANSS-UHFFFAOYSA-N

> <FORMULA>
C27H42O3

> <MOLECULAR_WEIGHT>
414.6206

> <EXACT_MASS>
414.31339521

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
49.65445052788634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-one

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
5.540385736999999

> <ALOGPS_LOGS>
-7.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0490905373511765

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
118.3878

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.92e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036941
     RDKit          3D
Smilagenone
 72 77  0  0  0  0  0  0  0  0999 V2000
    7.0458   -0.3835   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -0.7076    1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857   -1.6599    0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697   -1.2224    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604    0.1397    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510    0.9665    0.6688 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3474    0.5528    1.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807    0.6212    1.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5202    1.5320    0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289    1.5744    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425    1.5355   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0016    1.2345   -0.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    2.0577    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1667    1.8499    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6168    0.5487   -0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9898    0.2533    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4732   -1.1077    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6019   -1.3771   -0.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4920   -2.2217    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1761   -1.8212   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6143   -0.5476    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071   -0.8250    1.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544   -0.2062   -0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2696   -1.1395   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0947   -0.8214   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151    0.5194   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    0.4781   -2.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    1.0670   -0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405    0.0155   -0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8512    0.3907   -1.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0132   -0.8507    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1681    0.7112   -0.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7316   -0.7978   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585   -1.1463    1.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8814   -1.7130   -0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1645   -2.7037    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6556   -1.2249    2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8765   -1.9381    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1225    1.3483    1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9979    0.4403    2.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    2.5410    0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3139    0.7938    1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    2.5644    1.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161    2.5269   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420    1.7235   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819    1.9818    1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317    3.1383    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265    2.6592   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382    1.9139    1.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876    0.6599   -1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6904    0.9648   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1028    0.4662    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -3.1386   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906   -2.4650    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2670   -1.7306   -1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702   -2.6682   -0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -1.9196    1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -0.2750    2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3754   -0.5824    2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5873   -0.4961   -1.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233   -1.3020    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5317   -2.1603   -0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920   -0.9171    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -1.5803   -1.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2929   -0.5433   -3.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9408    0.7372   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    1.2229   -3.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274    1.8943   -1.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203   -1.0042   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -0.4612   -2.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7013    0.8446   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874    1.1899   -2.4920 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
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
  7  2  1  0
 28  9  1  0
 29  5  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  0
 29 69  1  0
 30 70  1  0
 30 71  1  0
 30 72  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.786  -0.440   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.786  -1.980   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.121  -1.210   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.455  -1.980   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.455  -3.520   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.121  -4.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.786  -3.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.454  -4.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.119  -3.520   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.119  -1.980   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.454  -1.210   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.454   0.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.119   1.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.213   0.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.375   1.862   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.213  -1.210   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.679  -1.685   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.585  -0.440   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.048   0.035   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.048   1.575   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.454   0.948   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.702   1.854   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.540   3.387   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.787   4.290   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.679   0.805   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.585   2.052   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.107   3.518   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.134   4.013   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.889   3.107   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -7.787  -4.290   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11    2   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   25                                             
CONECT   15   14                                                            
CONECT   16   10   14   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26   29                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23                                                            
CONECT   25   14   18   26                                                  
CONECT   26   20   25   27                                                  
CONECT   27   26                                                            
CONECT   28   23   29                                                       
CONECT   29   20   28                                                       
CONECT   30    5                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

COMPND    HMDB0036941
HETATM    1  C1  UNL     1       7.046  -0.383  -0.042  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.044  -0.708   1.043  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.986  -1.660   0.591  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.670  -1.222   1.161  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.260   0.140   0.643  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.351   0.967   0.669  1.00  0.00           O  
HETATM    7  C6  UNL     1       5.347   0.553   1.544  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.181   0.621   1.377  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.520   1.532   0.561  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.029   1.574   0.827  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.543   1.535  -0.554  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.002   1.235  -0.629  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.690   2.058   0.446  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.167   1.850   0.493  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.617   0.549  -0.128  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.990   0.253   0.386  1.00  0.00           C  
HETATM   17  C15 UNL     1      -6.473  -1.108   0.072  1.00  0.00           C  
HETATM   18  O3  UNL     1      -7.602  -1.377  -0.253  1.00  0.00           O  
HETATM   19  C16 UNL     1      -5.492  -2.222   0.167  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.176  -1.821  -0.489  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.614  -0.548   0.133  1.00  0.00           C  
HETATM   22  C19 UNL     1      -3.407  -0.825   1.578  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.354  -0.206  -0.627  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.270  -1.140  -0.188  1.00  0.00           C  
HETATM   25  C22 UNL     1       0.095  -0.821  -0.646  1.00  0.00           C  
HETATM   26  C23 UNL     1       0.315   0.519  -1.236  1.00  0.00           C  
HETATM   27  C24 UNL     1       0.128   0.478  -2.723  1.00  0.00           C  
HETATM   28  C25 UNL     1       1.700   1.067  -0.864  1.00  0.00           C  
HETATM   29  C26 UNL     1       2.741   0.016  -0.794  1.00  0.00           C  
HETATM   30  C27 UNL     1       3.851   0.391  -1.784  1.00  0.00           C  
HETATM   31  H1  UNL     1       8.013  -0.851   0.199  1.00  0.00           H  
HETATM   32  H2  UNL     1       7.168   0.711  -0.158  1.00  0.00           H  
HETATM   33  H3  UNL     1       6.732  -0.798  -1.027  1.00  0.00           H  
HETATM   34  H4  UNL     1       6.559  -1.146   1.923  1.00  0.00           H  
HETATM   35  H5  UNL     1       4.881  -1.713  -0.508  1.00  0.00           H  
HETATM   36  H6  UNL     1       5.164  -2.704   0.935  1.00  0.00           H  
HETATM   37  H7  UNL     1       3.656  -1.225   2.269  1.00  0.00           H  
HETATM   38  H8  UNL     1       2.877  -1.938   0.846  1.00  0.00           H  
HETATM   39  H9  UNL     1       6.123   1.348   1.550  1.00  0.00           H  
HETATM   40  H10 UNL     1       4.998   0.440   2.585  1.00  0.00           H  
HETATM   41  H11 UNL     1       1.986   2.541   0.667  1.00  0.00           H  
HETATM   42  H12 UNL     1      -0.314   0.794   1.500  1.00  0.00           H  
HETATM   43  H13 UNL     1      -0.183   2.564   1.298  1.00  0.00           H  
HETATM   44  H14 UNL     1      -0.316   2.527  -1.028  1.00  0.00           H  
HETATM   45  H15 UNL     1      -2.342   1.723  -1.595  1.00  0.00           H  
HETATM   46  H16 UNL     1      -2.182   1.982   1.430  1.00  0.00           H  
HETATM   47  H17 UNL     1      -2.532   3.138   0.144  1.00  0.00           H  
HETATM   48  H18 UNL     1      -4.726   2.659  -0.046  1.00  0.00           H  
HETATM   49  H19 UNL     1      -4.538   1.914   1.551  1.00  0.00           H  
HETATM   50  H20 UNL     1      -4.688   0.660  -1.236  1.00  0.00           H  
HETATM   51  H21 UNL     1      -6.690   0.965  -0.139  1.00  0.00           H  
HETATM   52  H22 UNL     1      -6.103   0.466   1.472  1.00  0.00           H  
HETATM   53  H23 UNL     1      -5.824  -3.139  -0.333  1.00  0.00           H  
HETATM   54  H24 UNL     1      -5.291  -2.465   1.225  1.00  0.00           H  
HETATM   55  H25 UNL     1      -4.267  -1.731  -1.579  1.00  0.00           H  
HETATM   56  H26 UNL     1      -3.470  -2.668  -0.244  1.00  0.00           H  
HETATM   57  H27 UNL     1      -3.242  -1.920   1.785  1.00  0.00           H  
HETATM   58  H28 UNL     1      -2.630  -0.275   2.088  1.00  0.00           H  
HETATM   59  H29 UNL     1      -4.375  -0.582   2.107  1.00  0.00           H  
HETATM   60  H30 UNL     1      -2.587  -0.496  -1.698  1.00  0.00           H  
HETATM   61  H31 UNL     1      -1.323  -1.302   0.912  1.00  0.00           H  
HETATM   62  H32 UNL     1      -1.532  -2.160  -0.606  1.00  0.00           H  
HETATM   63  H33 UNL     1       0.792  -0.917   0.239  1.00  0.00           H  
HETATM   64  H34 UNL     1       0.504  -1.580  -1.378  1.00  0.00           H  
HETATM   65  H35 UNL     1       0.293  -0.543  -3.076  1.00  0.00           H  
HETATM   66  H36 UNL     1      -0.941   0.737  -2.932  1.00  0.00           H  
HETATM   67  H37 UNL     1       0.821   1.223  -3.167  1.00  0.00           H  
HETATM   68  H38 UNL     1       1.927   1.894  -1.551  1.00  0.00           H  
HETATM   69  H39 UNL     1       2.420  -1.004  -0.986  1.00  0.00           H  
HETATM   70  H40 UNL     1       4.129  -0.461  -2.417  1.00  0.00           H  
HETATM   71  H41 UNL     1       4.701   0.845  -1.235  1.00  0.00           H  
HETATM   72  H42 UNL     1       3.487   1.190  -2.492  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    7   34
CONECT    3    4   35   36
CONECT    4    5   37   38
CONECT    5    6    8   29
CONECT    6    7
CONECT    7   39   40
CONECT    8    9
CONECT    9   10   28   41
CONECT   10   11   42   43
CONECT   11   12   26   44
CONECT   12   13   23   45
CONECT   13   14   46   47
CONECT   14   15   48   49
CONECT   15   16   21   50
CONECT   16   17   51   52
CONECT   17   18   18   19
CONECT   19   20   53   54
CONECT   20   21   55   56
CONECT   21   22   23
CONECT   22   57   58   59
CONECT   23   24   60
CONECT   24   25   61   62
CONECT   25   26   63   64
CONECT   26   27   28
CONECT   27   65   66   67
CONECT   28   29   68
CONECT   29   30   69
CONECT   30   70   71   72
END

HMDB0036941
     RDKit          3D
Smilagenone
 72 77  0  0  0  0  0  0  0  0999 V2000
    7.0458   -0.3835   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -0.7076    1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857   -1.6599    0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697   -1.2224    1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604    0.1397    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510    0.9665    0.6688 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3474    0.5528    1.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1807    0.6212    1.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5202    1.5320    0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289    1.5744    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425    1.5355   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0016    1.2345   -0.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    2.0577    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1667    1.8499    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6168    0.5487   -0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9898    0.2533    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4732   -1.1077    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6019   -1.3771   -0.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4920   -2.2217    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1761   -1.8212   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6143   -0.5476    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071   -0.8250    1.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544   -0.2062   -0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2696   -1.1395   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0947   -0.8214   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3151    0.5194   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    0.4781   -2.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    1.0670   -0.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405    0.0155   -0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8512    0.3907   -1.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0132   -0.8507    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1681    0.7112   -0.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7316   -0.7978   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585   -1.1463    1.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8814   -1.7130   -0.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1645   -2.7037    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6556   -1.2249    2.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8765   -1.9381    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1225    1.3483    1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9979    0.4403    2.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    2.5410    0.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3139    0.7938    1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    2.5644    1.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161    2.5269   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420    1.7235   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819    1.9818    1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317    3.1383    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265    2.6592   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382    1.9139    1.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6876    0.6599   -1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6904    0.9648   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1028    0.4662    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8245   -3.1386   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906   -2.4650    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2670   -1.7306   -1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702   -2.6682   -0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422   -1.9196    1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -0.2750    2.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3754   -0.5824    2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5873   -0.4961   -1.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233   -1.3020    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5317   -2.1603   -0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920   -0.9171    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037   -1.5803   -1.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2929   -0.5433   -3.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9408    0.7372   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    1.2229   -3.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274    1.8943   -1.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203   -1.0042   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -0.4612   -2.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7013    0.8446   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874    1.1899   -2.4920 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
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
  7  2  1  0
 28  9  1  0
 29  5  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  0
 29 69  1  0
 30 70  1  0
 30 71  1  0
 30 72  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5beta,25R)-Spirostan-3-one	HMDB
25-Episarsasapogenone	HMDB
Sarsasapogenone	HMDB
Spirostan-3-one	HMDB
Sarsasapogenone, (5alpha-25R)-isomer	MeSH

Chemical Formula

C₂₇H₄₂O₃

Average Molecular Weight

414.6206

Monoisotopic Molecular Weight

414.31339521

IUPAC Name

5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-one

Traditional Name

5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-one

CAS Registry Number

512-07-2

SMILES

CC1C2C(CC3C4CCC5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO1

InChI Identifier

InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-18,20-24H,5-15H2,1-4H3

InChI Key

CIBAPVLFORANSS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Spirostane skeleton
3-oxosteroid
Oxosteroid
Steroid
Ketal
Oxane
Tetrahydrofuran
Ketone
Cyclic ketone
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036941)
Cell membrane (HMDB: HMDB0036941)

Biofluid or Excreta

Urine (HMDB: HMDB0036941)

Tissue substructure

Hepatic tissue (HMDB: HMDB0036941)

Cellular substructure

Extracellular (HMDB: HMDB0036941)
Membrane (HMDB: HMDB0036941)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036941)

Source

Endogenous

Endogenous (HMDB: HMDB0036941)

Plant

Plant (HMDB: HMDB0036941)

Animal

Animal (HMDB: HMDB0036941)

Exogenous

Food

Food (HMDB: HMDB0036941)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036941)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036941)

Cellular process

Cell signaling (HMDB: HMDB0036941)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036941)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036941)

Nutrient

Nutrient (HMDB: HMDB0036941)

Molecular messenger

Signaling molecule (HMDB: HMDB0036941)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036941)

Emulsifier (HMDB: HMDB0036941)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	188 - 189 °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	2.9e-05 g/L	ALOGPS
logP	4.14	ALOGPS
logP	5.54	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	118.39 m³·mol⁻¹	ChemAxon
Polarizability	49.65 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	196.601	31661259
DarkChem	[M-H]-	191.155	31661259
DeepCCS	[M-2H]-	236.523	30932474
DeepCCS	[M+Na]+	212.103	30932474
AllCCS	[M+H]+	207.7	32859911
AllCCS	[M+H-H2O]+	205.6	32859911
AllCCS	[M+NH4]+	209.7	32859911
AllCCS	[M+Na]+	210.2	32859911
AllCCS	[M-H]-	206.2	32859911
AllCCS	[M+Na-2H]-	207.8	32859911
AllCCS	[M+HCOO]-	209.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Smilagenone	CC1C2C(CC3C4CCC5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO1	3536.8	Standard polar	33892256
Smilagenone	CC1C2C(CC3C4CCC5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO1	3127.6	Standard non polar	33892256
Smilagenone	CC1C2C(CC3C4CCC5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO1	3405.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Smilagenone,1TMS,isomer #1	CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C	3330.2	Semi standard non polar	33892256
Smilagenone,1TMS,isomer #1	CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C	3159.7	Standard non polar	33892256
Smilagenone,1TMS,isomer #2	CC1CCC2(OC1)OC1CC3C4CCC5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C	3357.5	Semi standard non polar	33892256
Smilagenone,1TMS,isomer #2	CC1CCC2(OC1)OC1CC3C4CCC5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C	3216.7	Standard non polar	33892256
Smilagenone,1TBDMS,isomer #1	CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C	3574.5	Semi standard non polar	33892256
Smilagenone,1TBDMS,isomer #1	CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C	3367.5	Standard non polar	33892256
Smilagenone,1TBDMS,isomer #2	CC1CCC2(OC1)OC1CC3C4CCC5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C	3598.1	Semi standard non polar	33892256
Smilagenone,1TBDMS,isomer #2	CC1CCC2(OC1)OC1CC3C4CCC5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C	3437.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Smilagenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4s-3159000000-542e7dc675517bf4ce05	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Smilagenone 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 - Smilagenone 10V, Positive-QTOF	splash10-014i-8048900000-9b13f9aa3b594130cff7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 20V, Positive-QTOF	splash10-00xr-8198200000-f32c85cf75f50873a5ab	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 40V, Positive-QTOF	splash10-066r-9054000000-b9d4208da6e48c4ee19a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 10V, Positive-QTOF	splash10-014i-8048900000-9b13f9aa3b594130cff7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 20V, Positive-QTOF	splash10-00xr-8198200000-f32c85cf75f50873a5ab	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 40V, Positive-QTOF	splash10-066r-9054000000-b9d4208da6e48c4ee19a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 10V, Negative-QTOF	splash10-03di-4011900000-2473bea931f335f7cac6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 20V, Negative-QTOF	splash10-03dj-2039300000-5c3b29791cfa45af139f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 40V, Negative-QTOF	splash10-014j-9033000000-b05e67e3a7880c576f3a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 10V, Negative-QTOF	splash10-03di-4011900000-2473bea931f335f7cac6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 20V, Negative-QTOF	splash10-03dj-2039300000-5c3b29791cfa45af139f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 40V, Negative-QTOF	splash10-014j-9033000000-b05e67e3a7880c576f3a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 10V, Positive-QTOF	splash10-014i-0013900000-8600851e1b5173533f01	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 20V, Positive-QTOF	splash10-00mk-1159300000-c0eba19fafc68510a6f7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 40V, Positive-QTOF	splash10-0036-3952000000-27be854367b89fd29eec	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 10V, Negative-QTOF	splash10-03di-0000900000-382bbcadd43c6789b832	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 20V, Negative-QTOF	splash10-03di-0000900000-af0d9054cd738c556ebf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Smilagenone 40V, Negative-QTOF	splash10-03di-0009500000-341b22116ef35ac10e8b	2021-09-24	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

FDB015910

KNApSAcK ID

Not Available

Chemspider ID

277091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

313275

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

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 Smilagenone (HMDB0036941)

MOL for HMDB0036941 (Smilagenone)

3D MOL for HMDB0036941 (Smilagenone)

3D SDF for HMDB0036941 (Smilagenone)

3D-SDF for HMDB0036941 (Smilagenone)

PDB for HMDB0036941 (Smilagenone)

3D PDB for HMDB0036941 (Smilagenone)

SMILES for HMDB0036941 (Smilagenone)

INCHI for HMDB0036941 (Smilagenone)

Structure for HMDB0036941 (Smilagenone)

3D Structure for HMDB0036941 (Smilagenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra