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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:23:28 UTC

Update Date

2021-09-26 23:10:35 UTC

HMDB ID

HMDB0255610

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nimbolide

Description

Nimbolide 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. Nimbolide is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Nimbolide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nimbolide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1533004171515142D          

 34 39  0  0  0  0            999 V2000
    2.4004    4.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0075    3.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273    3.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399    2.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4343    2.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541    1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8612    1.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    1.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6809    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3909   -0.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0099    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8313    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0115    1.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016    1.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825    1.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242    2.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7688    1.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9491    2.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7704    2.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0978    1.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4788    1.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -0.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304   -0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1718   -1.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    0.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8577    0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666    1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    1.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    2.7904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4668    1.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    2.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.7205    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  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  2  0  0  0  0
  7 15  1  0  0  0  0
 11 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 17 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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  6 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 22 34  1  0  0  0  0
 26 34  1  0  0  0  0
M  END

HMDB0255610
     RDKit          3D
Nimbolide
 64 69  0  0  0  0  0  0  0  0999 V2000
    0.5038    3.8415    4.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455    3.4262    2.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736    2.0539    2.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244    1.2774    3.3528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    1.6513    1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0282    0.2005    1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365   -0.6237    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5470   -1.3841    2.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059   -0.1467    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2210    0.7772   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0067    2.2416   -0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4751    0.1091   -0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723    0.7797   -1.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5031    1.1991   -1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8168    1.7863   -2.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7430    1.7236   -3.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7509    1.1370   -2.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697   -1.2968   -1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -1.4954    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139   -2.4491    0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0680   -1.7506   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -2.4602    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450   -3.5766   -0.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5996   -3.2711   -1.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8361   -3.8381   -2.6481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535   -2.0777   -1.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6925   -2.6649   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6770   -1.1491   -2.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0485   -0.0058   -2.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169    0.3565   -1.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0681    1.0784   -1.7763 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4223    0.5916    0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5350   -1.5860    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488    4.1588    3.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4628    2.9691    4.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217    4.6298    4.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0170    2.0676    1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4867   -0.2144    1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.3267    2.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8135   -2.4448    1.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700   -0.9745    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    2.7625   -0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    2.4169   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7130    2.7287    0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1078   -0.0290    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695    1.0849   -0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7897    2.2179   -3.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7447    0.9657   -3.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593   -1.1976   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -2.0027   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -1.6639    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -1.3128   -1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2003   -2.8262    1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5068   -2.9496    0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9288   -3.5586   -1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4850   -1.8952   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4550   -1.4323   -2.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2962    0.6964   -3.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3375    0.0418    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5044    1.6160    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4348    0.6333    1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1574   -1.7308    0.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 32  6  1  0
 21  7  1  0
 34 22  1  0
 19  9  1  0
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 17 13  2  0
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  1 37  1  0
  5 38  1  0
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 34 64  1  0
M  END


  Mrv1533004171515142D          

 34 39  0  0  0  0            999 V2000
    2.4004    4.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0075    3.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273    3.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399    2.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4343    2.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541    1.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8612    1.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    1.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6809    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3909   -0.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0099    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8313    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0115    1.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016    1.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825    1.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242    2.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7688    1.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9491    2.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7704    2.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0978    1.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4788    1.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -0.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304   -0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1718   -1.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    0.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8577    0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666    1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    1.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    2.7904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4668    1.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    2.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.7205    0.0000 C   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
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 22 23  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0255610

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)CC1C2(C)C(OC3CC(C(C)=C23)C2=COC=C2)C2OC(=O)C3(C)C=CC(=O)C1(C)C23

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O7/c1-13-15(14-7-9-32-12-14)10-16-20(13)27(4)17(11-19(29)31-5)26(3)18(28)6-8-25(2)22(26)21(23(27)33-16)34-24(25)30/h6-9,12,15-17,21-23H,10-11H2,1-5H3

> <INCHI_KEY>
JZIQWNPPBKFOPT-UHFFFAOYSA-N

> <FORMULA>
C27H30O7

> <MOLECULAR_WEIGHT>
466.53

> <EXACT_MASS>
466.199153306

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.34647617487529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
3.1439661966666677

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8590085361326616

> <JCHEM_POLAR_SURFACE_AREA>
92.03999999999999

> <JCHEM_REFRACTIVITY>
121.86489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255610
     RDKit          3D
Nimbolide
 64 69  0  0  0  0  0  0  0  0999 V2000
    0.5038    3.8415    4.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455    3.4262    2.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736    2.0539    2.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244    1.2774    3.3528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    1.6513    1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0282    0.2005    1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365   -0.6237    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5470   -1.3841    2.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059   -0.1467    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2210    0.7772   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0067    2.2416   -0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4751    0.1091   -0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723    0.7797   -1.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5031    1.1991   -1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8168    1.7863   -2.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7430    1.7236   -3.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7509    1.1370   -2.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697   -1.2968   -1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -1.4954    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139   -2.4491    0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0680   -1.7506   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -2.4602    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450   -3.5766   -0.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5996   -3.2711   -1.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8361   -3.8381   -2.6481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535   -2.0777   -1.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6925   -2.6649   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6770   -1.1491   -2.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0485   -0.0058   -2.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169    0.3565   -1.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0681    1.0784   -1.7763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1731   -0.1253    0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4223    0.5916    0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5350   -1.5860    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488    4.1588    3.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4628    2.9691    4.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217    4.6298    4.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442    2.2398    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0170    2.0676    1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4867   -0.2144    1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.3267    2.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8135   -2.4448    1.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700   -0.9745    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    2.7625   -0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    2.4169   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7130    2.7287    0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1078   -0.0290    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695    1.0849   -0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7897    2.2179   -3.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7447    0.9657   -3.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593   -1.1976   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -2.0027   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -1.6639    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -1.3128   -1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2003   -2.8262    1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5068   -2.9496    0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9288   -3.5586   -1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4850   -1.8952   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4550   -1.4323   -2.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2962    0.6964   -3.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3375    0.0418    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5044    1.6160    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4348    0.6333    1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1574   -1.7308    0.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 32  6  1  0
 21  7  1  0
 34 22  1  0
 19  9  1  0
 34 26  1  0
 17 13  2  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 14 48  1  0
 15 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 21 54  1  0
 22 55  1  0
 27 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  0
 29 60  1  0
 33 61  1  0
 33 62  1  0
 33 63  1  0
 34 64  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.481   8.399   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.614   7.356   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.278   5.853   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.808   5.393   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.411   4.811   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.074   3.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.208   2.265   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.699   3.724   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.871   0.762   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.196  -0.022   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.352   0.996   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.885   1.140   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.222   2.643   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.896   3.427   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.741   2.409   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.752   4.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.635   3.254   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.972   4.757   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.505   4.901   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      15.116   3.488   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.960   2.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.401   0.302   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.760  -1.098   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.230  -0.920   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.187  -2.053   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.926   0.589   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.671  -0.302   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.601   1.374   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.618   2.914   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.960   3.669   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.921   5.209   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.605   2.848   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.728   4.383   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.268   1.345   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8    9   15                                             
CONECT    8    7                                                            
CONECT    9    7   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    7   11                                                  
CONECT   16   14                                                            
CONECT   17   13   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17                                                       
CONECT   22    9   23   34                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   34                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    6   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   22   26                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

COMPND    HMDB0255610
HETATM    1  C1  UNL     1       0.504   3.842   4.027  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.146   3.426   2.858  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.274   2.054   2.535  1.00  0.00           C  
HETATM    4  O2  UNL     1       0.224   1.277   3.353  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.966   1.651   1.290  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.028   0.200   1.001  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.136  -0.624   0.832  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.547  -1.384   2.127  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.406  -0.147   0.255  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.221   0.777  -0.193  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.007   2.242  -0.289  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.475   0.109  -0.651  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.172   0.780  -1.733  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.503   1.199  -1.660  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.817   1.786  -2.856  1.00  0.00           C  
HETATM   16  O3  UNL     1       4.743   1.724  -3.599  1.00  0.00           O  
HETATM   17  C14 UNL     1       3.751   1.137  -2.972  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.970  -1.297  -1.022  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.107  -1.495   0.167  1.00  0.00           C  
HETATM   20  O4  UNL     1       1.114  -2.449   0.005  1.00  0.00           O  
HETATM   21  C17 UNL     1      -0.068  -1.751  -0.243  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.299  -2.460   0.120  1.00  0.00           C  
HETATM   23  O5  UNL     1      -1.645  -3.577  -0.651  1.00  0.00           O  
HETATM   24  C19 UNL     1      -2.600  -3.271  -1.578  1.00  0.00           C  
HETATM   25  O6  UNL     1      -2.836  -3.838  -2.648  1.00  0.00           O  
HETATM   26  C20 UNL     1      -3.354  -2.078  -1.066  1.00  0.00           C  
HETATM   27  C21 UNL     1      -4.692  -2.665  -0.557  1.00  0.00           C  
HETATM   28  C22 UNL     1      -3.677  -1.149  -2.160  1.00  0.00           C  
HETATM   29  C23 UNL     1      -3.049  -0.006  -2.274  1.00  0.00           C  
HETATM   30  C24 UNL     1      -2.017   0.356  -1.310  1.00  0.00           C  
HETATM   31  O7  UNL     1      -1.068   1.078  -1.776  1.00  0.00           O  
HETATM   32  C25 UNL     1      -2.173  -0.125   0.038  1.00  0.00           C  
HETATM   33  C26 UNL     1      -3.422   0.592   0.601  1.00  0.00           C  
HETATM   34  C27 UNL     1      -2.535  -1.586   0.048  1.00  0.00           C  
HETATM   35  H1  UNL     1       1.549   4.159   3.850  1.00  0.00           H  
HETATM   36  H2  UNL     1       0.463   2.969   4.739  1.00  0.00           H  
HETATM   37  H3  UNL     1      -0.122   4.630   4.489  1.00  0.00           H  
HETATM   38  H4  UNL     1      -0.644   2.240   0.423  1.00  0.00           H  
HETATM   39  H5  UNL     1      -2.017   2.068   1.485  1.00  0.00           H  
HETATM   40  H6  UNL     1      -1.487  -0.214   1.999  1.00  0.00           H  
HETATM   41  H7  UNL     1      -0.239  -1.327   2.895  1.00  0.00           H  
HETATM   42  H8  UNL     1       0.814  -2.445   1.880  1.00  0.00           H  
HETATM   43  H9  UNL     1       1.470  -0.974   2.566  1.00  0.00           H  
HETATM   44  H10 UNL     1       2.896   2.762  -0.712  1.00  0.00           H  
HETATM   45  H11 UNL     1       1.203   2.417  -1.032  1.00  0.00           H  
HETATM   46  H12 UNL     1       1.713   2.729   0.650  1.00  0.00           H  
HETATM   47  H13 UNL     1       4.108  -0.029   0.245  1.00  0.00           H  
HETATM   48  H14 UNL     1       6.170   1.085  -0.819  1.00  0.00           H  
HETATM   49  H15 UNL     1       6.790   2.218  -3.114  1.00  0.00           H  
HETATM   50  H16 UNL     1       2.745   0.966  -3.389  1.00  0.00           H  
HETATM   51  H17 UNL     1       2.459  -1.198  -1.979  1.00  0.00           H  
HETATM   52  H18 UNL     1       3.820  -2.003  -1.094  1.00  0.00           H  
HETATM   53  H19 UNL     1       2.734  -1.664   1.056  1.00  0.00           H  
HETATM   54  H20 UNL     1       0.034  -1.313  -1.221  1.00  0.00           H  
HETATM   55  H21 UNL     1      -1.200  -2.826   1.167  1.00  0.00           H  
HETATM   56  H22 UNL     1      -4.507  -2.950   0.493  1.00  0.00           H  
HETATM   57  H23 UNL     1      -4.929  -3.559  -1.128  1.00  0.00           H  
HETATM   58  H24 UNL     1      -5.485  -1.895  -0.636  1.00  0.00           H  
HETATM   59  H25 UNL     1      -4.455  -1.432  -2.876  1.00  0.00           H  
HETATM   60  H26 UNL     1      -3.296   0.696  -3.111  1.00  0.00           H  
HETATM   61  H27 UNL     1      -4.337   0.042   0.291  1.00  0.00           H  
HETATM   62  H28 UNL     1      -3.504   1.616   0.193  1.00  0.00           H  
HETATM   63  H29 UNL     1      -3.435   0.633   1.684  1.00  0.00           H  
HETATM   64  H30 UNL     1      -3.157  -1.731   0.990  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   38   39
CONECT    6    7   32   40
CONECT    7    8    9   21
CONECT    8   41   42   43
CONECT    9   10   10   19
CONECT   10   11   12
CONECT   11   44   45   46
CONECT   12   13   18   47
CONECT   13   14   17   17
CONECT   14   15   15   48
CONECT   15   16   49
CONECT   16   17
CONECT   17   50
CONECT   18   19   51   52
CONECT   19   20   53
CONECT   20   21
CONECT   21   22   54
CONECT   22   23   34   55
CONECT   23   24
CONECT   24   25   25   26
CONECT   26   27   28   34
CONECT   27   56   57   58
CONECT   28   29   29   59
CONECT   29   30   60
CONECT   30   31   31   32
CONECT   32   33   34
CONECT   33   61   62   63
CONECT   34   64
END

HMDB0255610
     RDKit          3D
Nimbolide
 64 69  0  0  0  0  0  0  0  0999 V2000
    0.5038    3.8415    4.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455    3.4262    2.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736    2.0539    2.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244    1.2774    3.3528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    1.6513    1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0282    0.2005    1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365   -0.6237    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5470   -1.3841    2.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059   -0.1467    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2210    0.7772   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0067    2.2416   -0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4751    0.1091   -0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723    0.7797   -1.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5031    1.1991   -1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8168    1.7863   -2.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7430    1.7236   -3.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7509    1.1370   -2.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697   -1.2968   -1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068   -1.4954    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139   -2.4491    0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0680   -1.7506   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -2.4602    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450   -3.5766   -0.6512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5996   -3.2711   -1.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8361   -3.8381   -2.6481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535   -2.0777   -1.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6925   -2.6649   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6770   -1.1491   -2.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0485   -0.0058   -2.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169    0.3565   -1.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0681    1.0784   -1.7763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1731   -0.1253    0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4223    0.5916    0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5350   -1.5860    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5488    4.1588    3.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4628    2.9691    4.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217    4.6298    4.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442    2.2398    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0170    2.0676    1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4867   -0.2144    1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.3267    2.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8135   -2.4448    1.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4700   -0.9745    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    2.7625   -0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    2.4169   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7130    2.7287    0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1078   -0.0290    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695    1.0849   -0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7897    2.2179   -3.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7447    0.9657   -3.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593   -1.1976   -1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -2.0027   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -1.6639    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -1.3128   -1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2003   -2.8262    1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5068   -2.9496    0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9288   -3.5586   -1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4850   -1.8952   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4550   -1.4323   -2.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2962    0.6964   -3.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3375    0.0418    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5044    1.6160    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4348    0.6333    1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1574   -1.7308    0.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 32  6  1  0
 21  7  1  0
 34 22  1  0
 19  9  1  0
 34 26  1  0
 17 13  2  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 14 48  1  0
 15 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 21 54  1  0
 22 55  1  0
 27 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  0
 29 60  1  0
 33 61  1  0
 33 62  1  0
 33 63  1  0
 34 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetic acid	Generator

Chemical Formula

C₂₇H₃₀O₇

Average Molecular Weight

466.53

Monoisotopic Molecular Weight

466.199153306

IUPAC Name

methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate

Traditional Name

methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C2(C)C(OC3CC(C(C)=C23)C2=COC=C2)C2OC(=O)C3(C)C=CC(=O)C1(C)C23

InChI Identifier

InChI=1S/C27H30O7/c1-13-15(14-7-9-32-12-14)10-16-20(13)27(4)17(11-19(29)31-5)26(3)18(28)6-8-25(2)22(26)21(23(27)33-16)34-24(25)30/h6-9,12,15-17,21-23H,10-11H2,1-5H3

InChI Key

JZIQWNPPBKFOPT-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
Naphthofuran
Cyclohexenone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Heteroaromatic compound
Methyl ester
Tetrahydrofuran
Furan
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Ether
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	3.76	ALOGPS
logP	3.14	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	92.04 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.86 m³·mol⁻¹	ChemAxon
Polarizability	48.35 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
DeepCCS	[M-2H]-	237.027	30932474
DeepCCS	[M+Na]+	212.453	30932474
AllCCS	[M+H]+	209.3	32859911
AllCCS	[M+H-H2O]+	207.2	32859911
AllCCS	[M+NH4]+	211.2	32859911
AllCCS	[M+Na]+	211.8	32859911
AllCCS	[M-H]-	215.9	32859911
AllCCS	[M+Na-2H]-	216.7	32859911
AllCCS	[M+HCOO]-	217.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nimbolide	COC(=O)CC1C2(C)C(OC3CC(C(C)=C23)C2=COC=C2)C2OC(=O)C3(C)C=CC(=O)C1(C)C23	4747.4	Standard polar	33892256
Nimbolide	COC(=O)CC1C2(C)C(OC3CC(C(C)=C23)C2=COC=C2)C2OC(=O)C3(C)C=CC(=O)C1(C)C23	3097.3	Standard non polar	33892256
Nimbolide	COC(=O)CC1C2(C)C(OC3CC(C(C)=C23)C2=COC=C2)C2OC(=O)C3(C)C=CC(=O)C1(C)C23	3433.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nimbolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1974700000-afeb12077a05b66fb48e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nimbolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

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

100017

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Nimbolide (HMDB0255610)

MOL for HMDB0255610 (Nimbolide)

3D MOL for HMDB0255610 (Nimbolide)

3D SDF for HMDB0255610 (Nimbolide)

3D-SDF for HMDB0255610 (Nimbolide)

PDB for HMDB0255610 (Nimbolide)

3D PDB for HMDB0255610 (Nimbolide)

SMILES for HMDB0255610 (Nimbolide)

INCHI for HMDB0255610 (Nimbolide)

Structure for HMDB0255610 (Nimbolide)

3D Structure for HMDB0255610 (Nimbolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra