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Showing metabocard for Chamissonolide (HMDB0341142)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 19:18:34 UTC
Update Date2022-09-22 18:35:02 UTC
HMDB IDHMDB0341142
Secondary Accession NumbersNone
Metabolite Identification
Common NameChamissonolide
Descriptionchamissonolide belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. Based on a literature review very few articles have been published on chamissonolide.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for HMDB0341142 (Chamissonolide)


  Mrv1652309092221562D          

 30 32  0  0  1  0            999 V2000
    0.3449   -1.9822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106   -1.6751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0366   -2.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893   -1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136   -0.3737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2525    0.3249    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904    0.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -0.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352   -0.4476    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4396   -0.6312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1496    0.1974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5885    0.8959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917    0.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746    0.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890   -0.4476    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6847   -0.6312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107   -0.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4392   -1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876   -2.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054   -1.2519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2684   -2.0761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -1.6099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5621   -0.7849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -2.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -1.2519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8558   -2.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  1  0  0  0
 26 29  1  0  0  0  0
  2 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
Download

3D MOL for HMDB0341142 (Chamissonolide)

Download
3D SDF for HMDB0341142 (Chamissonolide)

  Mrv1652309092221562D          

 30 32  0  0  1  0            999 V2000
    0.3449   -1.9822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106   -1.6751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0366   -2.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893   -1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136   -0.3737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2525    0.3249    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904    0.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -0.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352   -0.4476    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4396   -0.6312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1496    0.1974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5885    0.8959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917    0.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746    0.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890   -0.4476    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6847   -0.6312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107   -0.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4392   -1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876   -2.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054   -1.2519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2684   -2.0761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -1.6099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5621   -0.7849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -2.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -1.2519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8558   -2.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  1  0  0  0
 26 29  1  0  0  0  0
  2 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0341142

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(O)C[C@]([H])(OC(C)=O)[C@@]2([H])[C@]([H])(C)C[C@@]3([H])OC(=O)C(=C)[C@@]3([H])[C@]([H])(O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O6/c1-7-5-10-13(8(2)16(21)23-10)15(20)17(4)12(19)6-11(14(7)17)22-9(3)18/h7,10-15,19-20H,2,5-6H2,1,3-4H3/t7-,10-,11+,12-,13-,14-,15+,17-/m1/s1

> <INCHI_KEY>
TVXMVPIXPQJTJQ-ZBUGIYPBSA-N

> <FORMULA>
C17H24O6

> <MOLECULAR_WEIGHT>
324.373

> <EXACT_MASS>
324.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
33.264318670545755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,4S,4aS,5R,7S,7aS,8R,9aR)-4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-7-yl acetate

> <JCHEM_LOGP>
0.3451223333333346

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.801936207016759

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.054142237429197

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0031669675020547

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
80.05250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4S,4aS,5R,7S,7aS,8R,9aR)-4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3aH-azuleno[6,5-b]furan-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0341142 (Chamissonolide)
Download
PDB for HMDB0341142 (Chamissonolide)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  H   UNK     0       0.644  -3.700   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       2.073  -3.127   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.935  -4.661   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.913  -2.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.519  -0.698   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       2.338   0.606   0.000  0.00  0.00           H+0
HETATM    7  O   UNK     0       0.729   0.625   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.811   0.601   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.601   1.923   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.561  -0.744   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.052  -0.836   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       4.554  -1.178   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       4.013   0.368   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       4.832   1.672   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       3.344   1.756   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.553   0.368   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.513  -0.836   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       5.011  -1.178   0.000  0.00  0.00           H+0
HETATM   19  O   UNK     0       8.047  -0.698   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.652  -2.114   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.153  -2.456   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.492  -3.127   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.630  -4.661   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.170  -2.337   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       6.101  -3.875   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       4.783  -3.005   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       4.783  -1.465   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0       4.783  -4.545   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.395  -2.337   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.464  -3.875   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   29                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   13   29                                             
CONECT   12   11                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19   24                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26    2   11   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Download
3D PDB for HMDB0341142 (Chamissonolide)
Download
SMILES for HMDB0341142 (Chamissonolide)
[H][C@@]1(O)C[C@]([H])(OC(C)=O)[C@@]2([H])[C@]([H])(C)C[C@@]3([H])OC(=O)C(=C)[C@@]3([H])[C@]([H])(O)[C@]12C
Download
INCHI for HMDB0341142 (Chamissonolide)
InChI=1S/C17H24O6/c1-7-5-10-13(8(2)16(21)23-10)15(20)17(4)12(19)6-11(14(7)17)22-9(3)18/h7,10-15,19-20H,2,5-6H2,1,3-4H3/t7-,10-,11+,12-,13-,14-,15+,17-/m1/s1
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
ChamissonolidMeSH
2alpha-Acetoxy-2,3-dihydro-4betah-helenalinMeSH
Chemical FormulaC17H24O6
Average Molecular Weight324.373
Monoisotopic Molecular Weight324.157288493
IUPAC Name(3aS,4S,4aS,5R,7S,7aS,8R,9aR)-4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-7-yl acetate
Traditional Name(3aS,4S,4aS,5R,7S,7aS,8R,9aR)-4,5-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3aH-azuleno[6,5-b]furan-7-yl acetate
CAS Registry NumberNot Available
SMILES
[H][C@@]1(O)C[C@]([H])(OC(C)=O)[C@@]2([H])[C@]([H])(C)C[C@@]3([H])OC(=O)C(=C)[C@@]3([H])[C@]([H])(O)[C@]12C
InChI Identifier
InChI=1S/C17H24O6/c1-7-5-10-13(8(2)16(21)23-10)15(20)17(4)12(19)6-11(14(7)17)22-9(3)18/h7,10-15,19-20H,2,5-6H2,1,3-4H3/t7-,10-,11+,12-,13-,14-,15+,17-/m1/s1
InChI KeyTVXMVPIXPQJTJQ-ZBUGIYPBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentSesquiterpene lactones  
Alternative Parents
Substituents
  • Helenalin-skeleton
    • 

  • Ambrosanolide
    • 

  • Pseudoguaiane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Gamma butyrolactone
    • 

  • Cyclic alcohol
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Tetrahydrofuran
    • 

  • Enoate ester
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.35ChemAxon
pKa (Strongest Acidic)14.05ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.05 m³·mol⁻¹ChemAxon
Polarizability33.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Predicted Kovats Retention Indices
Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal  details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal  details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00021069  
Chemspider ID8194713  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10019140  
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864  ]