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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:41:33 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035684

Secondary Accession Numbers

HMDB35684

Metabolite Identification

Common Name

Deacetylnomilin

Description

Deacetylnomilin, also known as isolimonin, belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Deacetylnomilin 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 05061308382D          

 34 39  0  0  0  0            999 V2000
    4.2725    2.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2964    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0012   -0.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1035    0.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -2.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3999    1.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571   -0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -1.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1929   -1.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784    0.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    1.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5316    0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752    1.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1670    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219    1.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6866    0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    0.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1326    1.9077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3143   -0.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    1.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997   -2.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    0.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835    1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14  6  1  0  0  0  0
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 19 13  1  0  0  0  0
 21 20  1  0  0  0  0
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 22 15  1  0  0  0  0
 23  3  1  0  0  0  0
 23  8  1  0  0  0  0
 23 19  1  0  0  0  0
 24  4  1  0  0  0  0
 24 14  1  0  0  0  0
 24 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25  5  1  0  0  0  0
 25 14  1  0  0  0  0
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 26 23  1  0  0  0  0
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 31  9  1  0  0  0  0
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 32 19  1  0  0  0  0
 32 21  1  0  0  0  0
 33 18  1  0  0  0  0
 33 22  1  0  0  0  0
 34 20  1  0  0  0  0
 34 26  1  0  0  0  0
M  END

HMDB0035684
     RDKit          3D
Deacetylnomilin
 66 71  0  0  0  0  0  0  0  0999 V2000
   -4.4102    0.8397   -1.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.7362   -0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367    2.0947    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405   -0.1129    0.5235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4736   -1.4376    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4525   -2.1953    1.0443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1445   -2.0551    1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2356   -1.0433    1.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414   -0.2893    2.6342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148   -0.1645    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    1.0904    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4164    0.1649   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821    1.0091   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4192    0.3916   -1.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637    0.8534   -2.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381   -0.7691   -1.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122   -1.9690   -2.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100   -0.9517    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760   -1.0462    1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0854   -0.4003    0.9844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3530    0.0871   -0.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    1.5557   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    0.0509   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5540    0.9149    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9331    2.2385    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5494    2.6829    1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5558    1.7250    2.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9742    0.6597    1.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -1.2189   -0.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6093   -2.3219   -0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0642   -3.5084   -0.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557   -2.1145   -1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -1.2694   -2.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505   -0.8210   -1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2737    2.8818   -0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273   -2.4838    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4697   -0.2256    3.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    2.0221    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596    1.1252    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691    1.1718    2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128   -0.8123   -0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    1.0530   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4631   -2.2257   -2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2065   -1.7414   -2.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101   -2.8735   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481   -2.0182    0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964   -2.1367    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4235   -0.6915    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3364    0.4326    1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9144   -1.1545    1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026    2.0266   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0876    0.4553   -1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7802    2.8185   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8389   -0.2945    2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428   -3.0449   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  4  5  1  0
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  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
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 12 13  1  0
 13 14  1  0
 14 15  2  0
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 29 30  1  0
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 12  2  1  0
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 18 10  1  0
 34 21  1  0
 28 24  2  0
 34 32  1  0
  1 35  1  0
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  3 38  1  0
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 32 66  1  0
M  END


  Mrv0541 05061308382D          

 34 39  0  0  0  0            999 V2000
    4.2725    2.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2964    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0012   -0.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1035    0.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1830   -2.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3999    1.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571   -0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -1.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1929   -1.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784    0.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    1.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5316    0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752    1.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1670    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7219    1.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6866    0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    0.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5227    0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -1.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3143   -0.1488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3804    1.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997   -2.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    0.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835    1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
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 31  9  1  0  0  0  0
 31 12  1  0  0  0  0
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 33 18  1  0  0  0  0
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 34 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035684

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C4(C)C(CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O8/c1-22(2)15-10-17(28)25(5)14(24(15,4)16(27)11-18(29)33-22)6-8-23(3)19(13-7-9-31-12-13)32-21(30)20-26(23,25)34-20/h7,9,12,14-16,19-20,27H,6,8,10-11H2,1-5H3

> <INCHI_KEY>
HWAJASVMTDEFJN-UHFFFAOYSA-N

> <FORMULA>
C26H32O8

> <MOLECULAR_WEIGHT>
472.5275

> <EXACT_MASS>
472.209718

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
48.37774004160755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(furan-3-yl)-13-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.576258725333332

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.50166460077634

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.417265493119736

> <JCHEM_PKA_STRONGEST_BASIC>
-3.053322192083649

> <JCHEM_POLAR_SURFACE_AREA>
115.57000000000001

> <JCHEM_REFRACTIVITY>
116.45459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(furan-3-yl)-13-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035684
     RDKit          3D
Deacetylnomilin
 66 71  0  0  0  0  0  0  0  0999 V2000
   -4.4102    0.8397   -1.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.7362   -0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367    2.0947    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405   -0.1129    0.5235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4736   -1.4376    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4525   -2.1953    1.0443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1445   -2.0551    1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2356   -1.0433    1.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414   -0.2893    2.6342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148   -0.1645    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    1.0904    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4164    0.1649   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821    1.0091   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4192    0.3916   -1.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637    0.8534   -2.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381   -0.7691   -1.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122   -1.9690   -2.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100   -0.9517    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760   -1.0462    1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0854   -0.4003    0.9844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3530    0.0871   -0.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    1.5557   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    0.0509   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5540    0.9149    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9331    2.2385    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5494    2.6829    1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5558    1.7250    2.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9742    0.6597    1.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -1.2189   -0.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6093   -2.3219   -0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0642   -3.5084   -0.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557   -2.1145   -1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -1.2694   -2.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505   -0.8210   -1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988    1.8481   -2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5221    0.8342   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0990   -0.0032   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5198    2.1263    1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9019    2.4588    0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2737    2.8818   -0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273   -2.4838    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641   -2.9578    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817   -1.6297    2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697   -0.2256    3.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    2.0221    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596    1.1252    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691    1.1718    2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128   -0.8123   -0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    1.0530   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855    2.0700   -1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -2.2257   -2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2065   -1.7414   -2.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101   -2.8735   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481   -2.0182    0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964   -2.1367    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4235   -0.6915    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3364    0.4326    1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9144   -1.1545    1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026    2.0266   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977    1.8339   -0.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989    2.0334    0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    0.4553   -1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7802    2.8185   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9662    3.6956    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8389   -0.2945    2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428   -3.0449   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 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  2  0
 26 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 12  2  1  0
 34 16  1  0
 18 10  1  0
 34 21  1  0
 28 24  2  0
 34 32  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
 11 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 25 63  1  0
 26 64  1  0
 28 65  1  0
 32 66  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       7.975   3.828   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.887   3.641   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.869  -1.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.287  -0.876   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.927   0.226   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.886  -1.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.256  -3.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.378  -1.534   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.342  -4.644   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.346   3.158   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.253  -0.896   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.108  -2.617   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.360  -2.152   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.373   0.236   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.368   2.006   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.721  -0.747   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.838   2.849   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.326   0.209   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.847  -0.691   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.820   2.231   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.312   1.922   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.814   2.536   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.356  -0.382   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.882   0.545   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.351   1.388   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.842   1.079   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.921  -2.063   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.981   3.561   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      11.787  -0.278   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.710   3.074   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.119  -4.157   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.175   0.461   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.130   1.737   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.329   2.540   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   25                                                            
CONECT    6    8   14                                                       
CONECT    7    9   13                                                       
CONECT    8    6   23                                                       
CONECT    9    7   31                                                       
CONECT   10   15   17                                                       
CONECT   11   16   18                                                       
CONECT   12   13   31                                                       
CONECT   13    7   12   19                                                  
CONECT   14    6   24   25                                                  
CONECT   15   10   22   24                                                  
CONECT   16   11   24   27                                                  
CONECT   17   10   25   28                                                  
CONECT   18   11   29   33                                                  
CONECT   19   13   23   32                                                  
CONECT   20   21   26   34                                                  
CONECT   21   20   30   32                                                  
CONECT   22    1    2   15   33                                             
CONECT   23    3    8   19   26                                             
CONECT   24    4   14   15   16                                             
CONECT   25    5   14   17   26                                             
CONECT   26   20   23   25   34                                             
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   21                                                            
CONECT   31    9   12                                                       
CONECT   32   19   21                                                       
CONECT   33   18   22                                                       
CONECT   34   20   26                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

COMPND    HMDB0035684
HETATM    1  C1  UNL     1      -4.410   0.840  -1.574  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.734   0.736  -0.186  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.837   2.095   0.407  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.640  -0.113   0.524  1.00  0.00           O  
HETATM    5  C4  UNL     1      -4.474  -1.438   0.885  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.453  -2.195   1.044  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.145  -2.055   1.108  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.236  -1.043   1.700  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.941  -0.289   2.634  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.515  -0.164   0.677  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.031   1.090   1.364  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.416   0.165  -0.436  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.682   1.009  -1.469  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.419   0.392  -1.896  1.00  0.00           C  
HETATM   15  O4  UNL     1       0.164   0.853  -2.848  1.00  0.00           O  
HETATM   16  C12 UNL     1       0.138  -0.769  -1.188  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.312  -1.969  -2.078  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.310  -0.952   0.222  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.776  -1.046   1.239  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.085  -0.400   0.984  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.353   0.087  -0.392  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.044   1.556  -0.525  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.861   0.051  -0.615  1.00  0.00           C  
HETATM   24  C20 UNL     1       4.554   0.915   0.365  1.00  0.00           C  
HETATM   25  C21 UNL     1       4.933   2.239   0.108  1.00  0.00           C  
HETATM   26  C22 UNL     1       5.549   2.683   1.250  1.00  0.00           C  
HETATM   27  O5  UNL     1       5.556   1.725   2.140  1.00  0.00           O  
HETATM   28  C23 UNL     1       4.974   0.660   1.652  1.00  0.00           C  
HETATM   29  O6  UNL     1       4.397  -1.219  -0.571  1.00  0.00           O  
HETATM   30  C24 UNL     1       3.609  -2.322  -0.861  1.00  0.00           C  
HETATM   31  O7  UNL     1       4.064  -3.508  -0.660  1.00  0.00           O  
HETATM   32  C25 UNL     1       2.256  -2.115  -1.400  1.00  0.00           C  
HETATM   33  O8  UNL     1       2.173  -1.269  -2.496  1.00  0.00           O  
HETATM   34  C26 UNL     1       1.650  -0.821  -1.324  1.00  0.00           C  
HETATM   35  H1  UNL     1      -4.199   1.848  -2.006  1.00  0.00           H  
HETATM   36  H2  UNL     1      -5.522   0.834  -1.441  1.00  0.00           H  
HETATM   37  H3  UNL     1      -4.099  -0.003  -2.186  1.00  0.00           H  
HETATM   38  H4  UNL     1      -3.520   2.126   1.472  1.00  0.00           H  
HETATM   39  H5  UNL     1      -4.902   2.459   0.424  1.00  0.00           H  
HETATM   40  H6  UNL     1      -3.274   2.882  -0.101  1.00  0.00           H  
HETATM   41  H7  UNL     1      -2.827  -2.484   0.141  1.00  0.00           H  
HETATM   42  H8  UNL     1      -3.264  -2.958   1.779  1.00  0.00           H  
HETATM   43  H9  UNL     1      -1.482  -1.630   2.304  1.00  0.00           H  
HETATM   44  H10 UNL     1      -2.470  -0.226   3.502  1.00  0.00           H  
HETATM   45  H11 UNL     1      -1.226   2.022   0.791  1.00  0.00           H  
HETATM   46  H12 UNL     1       0.060   1.125   1.547  1.00  0.00           H  
HETATM   47  H13 UNL     1      -1.469   1.172   2.405  1.00  0.00           H  
HETATM   48  H14 UNL     1      -2.613  -0.812  -0.979  1.00  0.00           H  
HETATM   49  H15 UNL     1      -2.375   1.053  -2.370  1.00  0.00           H  
HETATM   50  H16 UNL     1      -1.586   2.070  -1.182  1.00  0.00           H  
HETATM   51  H17 UNL     1       0.463  -2.226  -2.829  1.00  0.00           H  
HETATM   52  H18 UNL     1      -1.207  -1.741  -2.658  1.00  0.00           H  
HETATM   53  H19 UNL     1      -0.410  -2.874  -1.428  1.00  0.00           H  
HETATM   54  H20 UNL     1      -0.748  -2.018   0.200  1.00  0.00           H  
HETATM   55  H21 UNL     1       0.996  -2.137   1.485  1.00  0.00           H  
HETATM   56  H22 UNL     1       0.423  -0.692   2.229  1.00  0.00           H  
HETATM   57  H23 UNL     1       2.336   0.433   1.678  1.00  0.00           H  
HETATM   58  H24 UNL     1       2.914  -1.154   1.193  1.00  0.00           H  
HETATM   59  H25 UNL     1       2.603   2.027  -1.365  1.00  0.00           H  
HETATM   60  H26 UNL     1       0.998   1.834  -0.489  1.00  0.00           H  
HETATM   61  H27 UNL     1       2.499   2.033   0.397  1.00  0.00           H  
HETATM   62  H28 UNL     1       4.088   0.455  -1.652  1.00  0.00           H  
HETATM   63  H29 UNL     1       4.780   2.819  -0.810  1.00  0.00           H  
HETATM   64  H30 UNL     1       5.966   3.696   1.372  1.00  0.00           H  
HETATM   65  H31 UNL     1       4.839  -0.295   2.181  1.00  0.00           H  
HETATM   66  H32 UNL     1       1.643  -3.045  -1.384  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    4   12
CONECT    3   38   39   40
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   41   42
CONECT    8    9   10   43
CONECT    9   44
CONECT   10   11   12   18
CONECT   11   45   46   47
CONECT   12   13   48
CONECT   13   14   49   50
CONECT   14   15   15   16
CONECT   16   17   18   34
CONECT   17   51   52   53
CONECT   18   19   54
CONECT   19   20   55   56
CONECT   20   21   57   58
CONECT   21   22   23   34
CONECT   22   59   60   61
CONECT   23   24   29   62
CONECT   24   25   28   28
CONECT   25   26   26   63
CONECT   26   27   64
CONECT   27   28
CONECT   28   65
CONECT   29   30
CONECT   30   31   31   32
CONECT   32   33   34   66
CONECT   33   34
END

HMDB0035684
     RDKit          3D
Deacetylnomilin
 66 71  0  0  0  0  0  0  0  0999 V2000
   -4.4102    0.8397   -1.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.7362   -0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367    2.0947    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6405   -0.1129    0.5235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4736   -1.4376    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4525   -2.1953    1.0443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1445   -2.0551    1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2356   -1.0433    1.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414   -0.2893    2.6342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148   -0.1645    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    1.0904    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4164    0.1649   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821    1.0091   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4192    0.3916   -1.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637    0.8534   -2.8484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381   -0.7691   -1.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122   -1.9690   -2.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100   -0.9517    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760   -1.0462    1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0854   -0.4003    0.9844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3530    0.0871   -0.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    1.5557   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    0.0509   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5540    0.9149    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9331    2.2385    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5494    2.6829    1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5558    1.7250    2.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9742    0.6597    1.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -1.2189   -0.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6093   -2.3219   -0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0642   -3.5084   -0.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2557   -2.1145   -1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -1.2694   -2.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505   -0.8210   -1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988    1.8481   -2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5221    0.8342   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0990   -0.0032   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5198    2.1263    1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9019    2.4588    0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2737    2.8818   -0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273   -2.4838    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641   -2.9578    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817   -1.6297    2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697   -0.2256    3.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    2.0221    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596    1.1252    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691    1.1718    2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128   -0.8123   -0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    1.0530   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855    2.0700   -1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -2.2257   -2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2065   -1.7414   -2.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101   -2.8735   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481   -2.0182    0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964   -2.1367    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4235   -0.6915    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3364    0.4326    1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9144   -1.1545    1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026    2.0266   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977    1.8339   -0.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989    2.0334    0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    0.4553   -1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7802    2.8185   -0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9662    3.6956    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8389   -0.2945    2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428   -3.0449   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 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  2  0
 26 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 12  2  1  0
 34 16  1  0
 18 10  1  0
 34 21  1  0
 28 24  2  0
 34 32  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
 11 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 25 63  1  0
 26 64  1  0
 28 65  1  0
 32 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isolimonin	HMDB

Chemical Formula

C₂₆H₃₂O₈

Average Molecular Weight

472.5275

Monoisotopic Molecular Weight

472.209718

IUPAC Name

7-(furan-3-yl)-13-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

Traditional Name

7-(furan-3-yl)-13-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

CAS Registry Number

3264-90-2

SMILES

CC12CCC3C4(C)C(CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4O

InChI Identifier

InChI=1S/C26H32O8/c1-22(2)15-10-17(28)25(5)14(24(15,4)16(27)11-18(29)33-22)6-8-23(3)19(13-7-9-31-12-13)32-21(30)20-26(23,25)34-20/h7,9,12,14-16,19-20,27H,6,8,10-11H2,1-5H3

InChI Key

HWAJASVMTDEFJN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Naphthopyran
Naphthalene
Caprolactone
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Oxepane
Oxane
Pyran
Dicarboxylic acid or derivatives
Heteroaromatic compound
Furan
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0035684)
Cell membrane (HMDB: HMDB0035684)

Cellular substructure

Extracellular (HMDB: HMDB0035684)
Membrane (HMDB: HMDB0035684)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035684)

Source

Endogenous

Endogenous (HMDB: HMDB0035684)

Plant

Plant (HMDB: HMDB0035684)

Animal

Animal (HMDB: HMDB0035684)

Exogenous

Food

Food (HMDB: HMDB0035684)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Citrus (FooDB: FOOD00859)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035684)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035684)

Cellular process

Cell signaling (HMDB: HMDB0035684)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035684)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035684)

Nutrient

Nutrient (HMDB: HMDB0035684)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035684)

Emulsifier (HMDB: HMDB0035684)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	263 - 265 °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	0.084 g/L	ALOGPS
logP	2.7	ALOGPS
logP	2.58	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	115.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.45 m³·mol⁻¹	ChemAxon
Polarizability	48.38 Å³	ChemAxon
Number of Rings	6	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]+	206.828	31661259
DarkChem	[M-H]-	197.772	31661259
DeepCCS	[M-2H]-	237.041	30932474
DeepCCS	[M+Na]+	212.463	30932474
AllCCS	[M+H]+	209.3	32859911
AllCCS	[M+H-H2O]+	207.3	32859911
AllCCS	[M+NH4]+	211.1	32859911
AllCCS	[M+Na]+	211.6	32859911
AllCCS	[M-H]-	214.4	32859911
AllCCS	[M+Na-2H]-	215.5	32859911
AllCCS	[M+HCOO]-	216.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deacetylnomilin	CC12CCC3C4(C)C(CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4O	3933.5	Standard polar	33892256
Deacetylnomilin	CC12CCC3C4(C)C(CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4O	3064.5	Standard non polar	33892256
Deacetylnomilin	CC12CCC3C4(C)C(CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4O	4101.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Deacetylnomilin,1TMS,isomer #1	CC1(C)OC(=O)CC(O[Si](C)(C)C)C2(C)C1CC(=O)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3632.6	Semi standard non polar	33892256
Deacetylnomilin,1TMS,isomer #2	CC1(C)OC(=O)CC(O)C2(C)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3615.4	Semi standard non polar	33892256
Deacetylnomilin,2TMS,isomer #1	CC1(C)OC(=O)CC(O[Si](C)(C)C)C2(C)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3551.1	Semi standard non polar	33892256
Deacetylnomilin,2TMS,isomer #1	CC1(C)OC(=O)CC(O[Si](C)(C)C)C2(C)C1C=C(O[Si](C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3285.2	Standard non polar	33892256
Deacetylnomilin,1TBDMS,isomer #1	CC1(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C2(C)C1CC(=O)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3876.8	Semi standard non polar	33892256
Deacetylnomilin,1TBDMS,isomer #2	CC1(C)OC(=O)CC(O)C2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3866.4	Semi standard non polar	33892256
Deacetylnomilin,2TBDMS,isomer #1	CC1(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3999.0	Semi standard non polar	33892256
Deacetylnomilin,2TBDMS,isomer #1	CC1(C)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CCC2(C)C(C3=COC=C3)OC(=O)C3OC321	3733.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Deacetylnomilin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01si-2259800000-a4d140cdff7bea3a3998	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deacetylnomilin GC-MS (1 TMS) - 70eV, Positive	splash10-003r-7064490000-0939502d59b9f57a162d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deacetylnomilin 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 - Deacetylnomilin 10V, Positive-QTOF	splash10-0ab9-0001900000-ac2fd55de38221c65f6b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 20V, Positive-QTOF	splash10-0a4u-0025900000-3428d6398664c9707925	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 40V, Positive-QTOF	splash10-00kb-9416000000-5b63ee7c0bd320d2261e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 10V, Negative-QTOF	splash10-00b9-0001900000-7c933e17bd71d8b72217	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 20V, Negative-QTOF	splash10-0umj-1006900000-28026242e599d86106f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 40V, Negative-QTOF	splash10-0a4m-9107200000-389a14bbe7886e74cb64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 10V, Positive-QTOF	splash10-00di-0000900000-6e029cb28edf4d9b8aa3	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 20V, Positive-QTOF	splash10-00di-0141900000-968227572d16a11da18f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 40V, Positive-QTOF	splash10-000i-2921200000-cd914e3f6b6a42b6f420	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 10V, Negative-QTOF	splash10-00di-0000900000-6092626f870c8a12f250	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 20V, Negative-QTOF	splash10-00di-0000900000-c9163d595834a7b09573	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deacetylnomilin 40V, Negative-QTOF	splash10-0006-4013900000-8418108a5da482d487cc	2021-09-25	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

FDB014401

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13857953

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 Deacetylnomilin (HMDB0035684)

MOL for HMDB0035684 (Deacetylnomilin)

3D MOL for HMDB0035684 (Deacetylnomilin)

3D SDF for HMDB0035684 (Deacetylnomilin)

3D-SDF for HMDB0035684 (Deacetylnomilin)

PDB for HMDB0035684 (Deacetylnomilin)

3D PDB for HMDB0035684 (Deacetylnomilin)

SMILES for HMDB0035684 (Deacetylnomilin)

INCHI for HMDB0035684 (Deacetylnomilin)

Structure for HMDB0035684 (Deacetylnomilin)

3D Structure for HMDB0035684 (Deacetylnomilin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra