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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:51:42 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036695

Secondary Accession Numbers

HMDB36695

Metabolite Identification

Common Name

Crispolide

Description

Crispolide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on Crispolide.

Structure

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

HMDB0036695
     RDKit          3D
Crispolide
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.2399    1.3398    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4321    0.3567    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642   -1.0545    0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7670   -1.5909    0.6763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777   -1.7529    0.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -0.7527    0.1583 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0729    0.3351   -0.6096 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4468    1.6675   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0304    1.7566   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415    1.0620    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614   -0.0376    1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0528   -1.2646    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3309   -2.4632    1.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.0995   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    0.1247   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431    1.4168   -0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8817    2.4410    0.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037    3.4018   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2186   -1.3839   -0.3552 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4188   -2.7476   -0.5657 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485    2.3822    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    1.1444    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -0.4477    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -0.0603   -1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6078    2.0928   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0120    2.3460    0.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    2.7737   -0.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3168   -0.0082    2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0374   -0.0165    1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502   -3.3572    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4119   -2.6181    1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8285   -2.3915    2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -1.9871   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929   -1.0439   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6594    0.0601    0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    0.1382   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708    1.6746   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4532    3.5852   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -0.9682   -1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022   -3.0532    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
  7  2  1  0
 16 10  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  1
  7 24  1  6
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  6
 18 38  1  0
 19 39  1  6
 20 40  1  0
M  END


  Mrv1652307201900042D          

 25 27  0  0  1  0            999 V2000
    5.7213    1.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -1.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1572    1.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055    1.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851   -0.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457    0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3160    0.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4216    0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4966    0.6609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5838    0.7668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3332   -0.1477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6033   -0.6157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6592    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7394   -0.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7776   -1.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4678   -0.1582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    1.1987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0517   -0.5530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0275    1.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9788    2.2625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6901    0.4874    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171    1.5581    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -0.9723    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291    0.1906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  8  1  2  0  0  0  0
  9  3  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15  2  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 13 16  1  6  0  0  0
 17 14  2  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
 11 20  1  1  0  0  0
 20 18  1  0  0  0  0
 21  3  1  0  0  0  0
 10 22  1  6  0  0  0
 11 23  1  6  0  0  0
 12 24  1  1  0  0  0
 13 25  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0036695

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C1=C2\CC(C)(CC[C@@]2([H])OO)[C@]([H])(O)[C@@]2([H])OC(=O)C(=C)[C@]2([H])C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-8-10-4-3-9-7-15(2,6-5-11(9)20-18)13(16)12(10)19-14(8)17/h3,10-13,16,18H,1,4-7H2,2H3/b9-3+/t10-,11+,12-,13+,15?/m0/s1

> <INCHI_KEY>
JXXWNBNYEWOORY-IIHAKNSESA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.32

> <EXACT_MASS>
280.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.770596974445894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,7S,11R)-11-hydroperoxy-2-hydroxy-1-methyl-6-methylidene-4-oxatricyclo[8.3.1.0^{3,7}]tetradec-9-en-5-one

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
1.7571193836666674

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.71269820783241

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.706927371526595

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3638692276072852

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
71.3955

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,7S,11R)-11-hydroperoxy-2-hydroxy-1-methyl-6-methylidene-4-oxatricyclo[8.3.1.0^{3,7}]tetradec-9-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036695
     RDKit          3D
Crispolide
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.2399    1.3398    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4321    0.3567    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642   -1.0545    0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7670   -1.5909    0.6763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777   -1.7529    0.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -0.7527    0.1583 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0729    0.3351   -0.6096 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4468    1.6675   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0304    1.7566   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415    1.0620    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614   -0.0376    1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0528   -1.2646    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3309   -2.4632    1.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.0995   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    0.1247   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431    1.4168   -0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8817    2.4410    0.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037    3.4018   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2186   -1.3839   -0.3552 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4188   -2.7476   -0.5657 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485    2.3822    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    1.1444    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -0.4477    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -0.0603   -1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6078    2.0928   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0120    2.3460    0.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    2.7737   -0.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3168   -0.0082    2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0374   -0.0165    1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502   -3.3572    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4119   -2.6181    1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8285   -2.3915    2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -1.9871   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929   -1.0439   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6594    0.0601    0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    0.1382   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708    1.6746   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4532    3.5852   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -0.9682   -1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022   -3.0532    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
  7  2  1  0
 16 10  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  1
  7 24  1  6
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  6
 18 38  1  0
 19 39  1  6
 20 40  1  0
M  END

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0      10.680   2.751   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.131  -2.454   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.893   2.720   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.477   2.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.419  -0.052   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.519  -1.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.939   0.490   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.923   1.410   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.520   1.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.394   1.234   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.956   1.431   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.089  -0.276   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.726  -1.149   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.564   0.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.113  -0.915   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.051  -2.654   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.073  -0.295   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.414   2.238   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.430  -1.032   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.918   2.568   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       5.561   4.223   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       6.888   0.910   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.392   2.908   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       8.132  -1.815   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       6.401   0.356   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   15                                                            
CONECT    3    4    9   21                                                  
CONECT    4    3   10                                                       
CONECT    5    6   11                                                       
CONECT    6    5   15                                                       
CONECT    7    9   15                                                       
CONECT    8    1   10   14                                                  
CONECT    9    3    7   11                                                  
CONECT   10    4    8   12   22                                             
CONECT   11    5    9   20   23                                             
CONECT   12   10   13   19   24                                             
CONECT   13   12   15   16   25                                             
CONECT   14    8   17   19                                                  
CONECT   15    2    6    7   13                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   20                                                            
CONECT   19   12   14                                                       
CONECT   20   11   18                                                       
CONECT   21    3                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0036695
HETATM    1  C1  UNL     1       4.240   1.340   0.294  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.432   0.357   0.032  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.664  -1.054   0.316  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.767  -1.591   0.676  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.478  -1.753   0.132  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.427  -0.753   0.158  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.073   0.335  -0.610  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.447   1.668  -0.667  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.030   1.757  -0.218  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.941   1.062   0.293  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.061  -0.038   1.327  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.053  -1.265   0.437  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.331  -2.463   1.301  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.223  -1.099  -0.507  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.065   0.125  -0.257  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.243   1.417  -0.317  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.882   2.441   0.369  1.00  0.00           O  
HETATM   18  O4  UNL     1      -3.204   3.402  -0.469  1.00  0.00           O  
HETATM   19  C15 UNL     1       0.219  -1.384  -0.355  1.00  0.00           C  
HETATM   20  O5  UNL     1       0.419  -2.748  -0.566  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.049   2.382   0.075  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.185   1.144   0.766  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.430  -0.448   1.218  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.271  -0.060  -1.651  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.608   2.093  -1.682  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.012   2.346   0.008  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.306   2.774  -0.385  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.317  -0.008   2.106  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.037  -0.016   1.847  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.950  -3.357   0.737  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.412  -2.618   1.480  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.829  -2.392   2.291  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.902  -1.987  -0.465  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.893  -1.044  -1.567  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.659   0.060   0.685  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.841   0.138  -1.064  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.171   1.675  -1.388  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.453   3.585  -1.086  1.00  0.00           H  
HETATM   39  H19 UNL     1       0.020  -0.968  -1.389  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.002  -3.053   0.200  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   19   23
CONECT    7    8   24
CONECT    8    9   25   26
CONECT    9   10   10   27
CONECT   10   11   16
CONECT   11   12   28   29
CONECT   12   13   14   19
CONECT   13   30   31   32
CONECT   14   15   33   34
CONECT   15   16   35   36
CONECT   16   17   37
CONECT   17   18
CONECT   18   38
CONECT   19   20   39
CONECT   20   40
END

HMDB0036695
     RDKit          3D
Crispolide
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.2399    1.3398    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4321    0.3567    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642   -1.0545    0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7670   -1.5909    0.6763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777   -1.7529    0.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -0.7527    0.1583 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0729    0.3351   -0.6096 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4468    1.6675   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0304    1.7566   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415    1.0620    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0614   -0.0376    1.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0528   -1.2646    0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3309   -2.4632    1.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.0995   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    0.1247   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431    1.4168   -0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8817    2.4410    0.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037    3.4018   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2186   -1.3839   -0.3552 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4188   -2.7476   -0.5657 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485    2.3822    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1854    1.1444    0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -0.4477    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -0.0603   -1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6078    2.0928   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0120    2.3460    0.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    2.7737   -0.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3168   -0.0082    2.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0374   -0.0165    1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502   -3.3572    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4119   -2.6181    1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8285   -2.3915    2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -1.9871   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929   -1.0439   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6594    0.0601    0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    0.1382   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708    1.6746   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4532    3.5852   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -0.9682   -1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022   -3.0532    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
  7  2  1  0
 16 10  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  1
  7 24  1  6
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  6
 18 38  1  0
 19 39  1  6
 20 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1b-Hydroperoxy-5b-hydroxy-4,14-cyclo-9,11-germacradien-12,6a-olide	HMDB

Chemical Formula

C₁₅H₂₀O₅

Average Molecular Weight

280.32

Monoisotopic Molecular Weight

280.131073744

IUPAC Name

(2S,3S,7S,11R)-11-hydroperoxy-2-hydroxy-1-methyl-6-methylidene-4-oxatricyclo[8.3.1.0^{3,7}]tetradec-9-en-5-one

Traditional Name

(2S,3S,7S,11R)-11-hydroperoxy-2-hydroxy-1-methyl-6-methylidene-4-oxatricyclo[8.3.1.0^{3,7}]tetradec-9-en-5-one

CAS Registry Number

83217-86-1

SMILES

[H]\C1=C2\CC(C)(CC[C@@]2([H])OO)[C@]([H])(O)[C@@]2([H])OC(=O)C(=C)[C@]2([H])C1

InChI Identifier

InChI=1S/C15H20O5/c1-8-10-4-3-9-7-15(2,6-5-11(9)20-18)13(16)12(10)19-14(8)17/h3,10-13,16,18H,1,4-7H2,2H3/b9-3+/t10-,11+,12-,13+,15?/m0/s1

InChI Key

JXXWNBNYEWOORY-IIHAKNSESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Hydroperoxide
Secondary alcohol
Carboxylic acid derivative
Peroxol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Alkyl hydroperoxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

bitter

Disposition

Biological location

Cellular substructure

Herbs and Spices (FooDB: FOOD00866)

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	20090 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.14 g/L	ALOGPS
logP	1.21	ALOGPS
logP	1.76	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.4 m³·mol⁻¹	ChemAxon
Polarizability	28.77 Å³	ChemAxon
Number of Rings	3	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]+	165.708	31661259
DarkChem	[M-H]-	161.804	31661259
DeepCCS	[M+H]+	165.531	30932474
DeepCCS	[M-H]-	163.373	30932474
DeepCCS	[M-2H]-	196.895	30932474
DeepCCS	[M+Na]+	171.411	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.7	32859911
AllCCS	[M+NH4]+	170.1	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	168.7	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Crispolide	[H]\C1=C2\CC(C)(CC[C@@]2([H])OO)[C@]([H])(O)[C@@]2([H])OC(=O)C(=C)[C@]2([H])C1	3399.8	Standard polar	33892256
Crispolide	[H]\C1=C2\CC(C)(CC[C@@]2([H])OO)[C@]([H])(O)[C@@]2([H])OC(=O)C(=C)[C@]2([H])C1	2117.8	Standard non polar	33892256
Crispolide	[H]\C1=C2\CC(C)(CC[C@@]2([H])OO)[C@]([H])(O)[C@@]2([H])OC(=O)C(=C)[C@]2([H])C1	2455.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Crispolide,1TMS,isomer #1	C=C1C(=O)O[C@H]2[C@H]1C/C=C1/CC(C)(CC[C@H]1OO)[C@@H]2O[Si](C)(C)C	2421.2	Semi standard non polar	33892256
Crispolide,1TBDMS,isomer #1	C=C1C(=O)O[C@H]2[C@H]1C/C=C1/CC(C)(CC[C@H]1OO)[C@@H]2O[Si](C)(C)C(C)(C)C	2638.2	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 - Crispolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zg0-1940000000-e030fc44b3940015343a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Crispolide GC-MS (1 TMS) - 70eV, Positive	splash10-0079-6869000000-00cea548e2553bbd24c5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Crispolide 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 - Crispolide 10V, Positive-QTOF	splash10-001i-0090000000-ff4cd129993fc0e1342b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 20V, Positive-QTOF	splash10-06sr-0290000000-c7473c8da004393f2239	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 40V, Positive-QTOF	splash10-0006-3940000000-7f232a2cb895b35704c3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 10V, Negative-QTOF	splash10-004i-0090000000-992a143d3eb7244d48b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 20V, Negative-QTOF	splash10-01ti-0090000000-2e6408dd809d549b8bf4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 40V, Negative-QTOF	splash10-0zfs-9060000000-efe75263a4b311ebb0b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 10V, Positive-QTOF	splash10-0002-0090000000-2cb14853e10b3483a75b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 20V, Positive-QTOF	splash10-0002-0090000000-3487fc3ae6103a394c4a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 40V, Positive-QTOF	splash10-0ab9-1960000000-bb191514460e9a8bec1a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 10V, Negative-QTOF	splash10-004i-0090000000-043a95ec3a9c60d0d2b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 20V, Negative-QTOF	splash10-002b-0090000000-610032dcf8bf88ba5792	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crispolide 40V, Negative-QTOF	splash10-00l7-0190000000-fd68ff99a61f624b358e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB015629

KNApSAcK ID

C00012420

Chemspider ID

68894490

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752041

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856541

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 Crispolide (HMDB0036695)

MOL for HMDB0036695 (Crispolide)

3D MOL for HMDB0036695 (Crispolide)

3D SDF for HMDB0036695 (Crispolide)

3D-SDF for HMDB0036695 (Crispolide)

PDB for HMDB0036695 (Crispolide)

3D PDB for HMDB0036695 (Crispolide)

SMILES for HMDB0036695 (Crispolide)

INCHI for HMDB0036695 (Crispolide)

Structure for HMDB0036695 (Crispolide)

3D Structure for HMDB0036695 (Crispolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra