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Showing metabocard for Epinepetalactone (HMDB0035063)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:00:22 UTC
Update Date2022-03-07 02:54:20 UTC
HMDB IDHMDB0035063
Secondary Accession Numbers
  • HMDB35063
Metabolite Identification
Common NameEpinepetalactone
DescriptionEpinepetalactone belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on Epinepetalactone.
Structure
Data?1563862659
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035063 (Epinepetalactone)

  Mrv0541 02241217202D          

 12 13  0  0  0  0            999 V2000
   -1.7401   -0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9305   -0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685   -1.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403   -1.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401    0.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305    0.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    1.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3637    1.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3637    0.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4168   -1.0116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for HMDB0035063 (Epinepetalactone)

HMDB0035063
     RDKit          3D
Epinepetalactone
 26 27  0  0  0  0  0  0  0  0999 V2000
   -3.0097   -0.2884   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8878    0.1012    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025    0.1960    1.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117    0.5536    2.4500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1635    0.8092    1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9432    1.6477    2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4662    0.0032    0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    0.3382   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574   -0.1937    0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4159   -0.3578   -1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122   -0.4317   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804    0.3890   -0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9829    0.0980   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422   -1.3845   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8626    0.1991   -1.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1147   -0.0149    1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -1.0863    0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453    1.4121   -0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -1.2788    0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8111    0.0955   -0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829    0.2824    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -1.4039   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8700    0.1640   -2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725   -1.4597   -1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    0.1338   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4988    1.4765   -0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12  2  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
M  END
Download

3D SDF for HMDB0035063 (Epinepetalactone)

  Mrv0541 02241217202D          

 12 13  0  0  0  0            999 V2000
   -1.7401   -0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9305   -0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685   -1.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403   -1.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401    0.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305    0.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    1.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3637    1.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3637    0.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4168   -1.0116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035063

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C1C(=O)OC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3

> <INCHI_KEY>
ZDKZHVNKFOXMND-UHFFFAOYSA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.217

> <EXACT_MASS>
166.099379692

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.15079988022303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-one

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
1.947327520666667

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.205270434744483

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
45.75470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nepetalactone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0035063 (Epinepetalactone)

HMDB0035063
     RDKit          3D
Epinepetalactone
 26 27  0  0  0  0  0  0  0  0999 V2000
   -3.0097   -0.2884   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8878    0.1012    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025    0.1960    1.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117    0.5536    2.4500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1635    0.8092    1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9432    1.6477    2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4662    0.0032    0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    0.3382   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574   -0.1937    0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4159   -0.3578   -1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122   -0.4317   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804    0.3890   -0.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9829    0.0980   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422   -1.3845   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8626    0.1991   -1.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1147   -0.0149    1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -1.0863    0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453    1.4121   -0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -1.2788    0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8111    0.0955   -0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829    0.2824    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -1.4039   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8700    0.1640   -2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725   -1.4597   -1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    0.1338   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4988    1.4765   -0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12  2  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
M  END
Download

PDB for HMDB0035063 (Epinepetalactone)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.248  -0.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.737  -0.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.435  -2.040   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.075  -2.493   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.248   1.283   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.737   1.283   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.831   2.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.679   2.039   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.679   0.528   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.831   0.075   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.133  -1.435   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.645  -1.888   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3   11                                                       
CONECT    5    6                                                            
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    2    8   10                                                  
CONECT   10    6    9   11                                                  
CONECT   11    4   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for HMDB0035063 (Epinepetalactone)

COMPND    HMDB0035063
HETATM    1  C1  UNL     1      -3.010  -0.288  -0.690  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.888   0.101   0.220  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.103   0.196   1.512  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.112   0.554   2.450  1.00  0.00           O  
HETATM    5  C4  UNL     1       0.164   0.809   1.901  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.943   1.648   2.389  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.466   0.003   0.724  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.700   0.338  -0.031  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.957  -0.194   0.599  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.416  -0.358  -1.370  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.112  -0.432  -1.481  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.580   0.389  -0.322  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.983   0.098  -0.306  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.042  -1.384  -0.853  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.863   0.199  -1.677  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.115  -0.015   1.894  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.372  -1.086   0.902  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.745   1.412  -0.245  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.850  -1.279   0.743  1.00  0.00           H  
HETATM   20  H8  UNL     1       3.811   0.095  -0.040  1.00  0.00           H  
HETATM   21  H9  UNL     1       3.083   0.282   1.569  1.00  0.00           H  
HETATM   22  H10 UNL     1       1.784  -1.404  -1.235  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.870   0.164  -2.212  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.472  -1.460  -1.477  1.00  0.00           H  
HETATM   25  H13 UNL     1      -0.383   0.134  -2.415  1.00  0.00           H  
HETATM   26  H14 UNL     1      -0.499   1.477  -0.551  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3   12
CONECT    3    4   16
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   12   17
CONECT    8    9   10   18
CONECT    9   19   20   21
CONECT   10   11   22   23
CONECT   11   12   24   25
CONECT   12   26
END
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SMILES for HMDB0035063 (Epinepetalactone)

CC1CCC2C1C(=O)OC=C2C
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INCHI for HMDB0035063 (Epinepetalactone)

InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Nepetalactone, 4aa,7a,7abHMDB
trans-cis-NepetalactoneHMDB
trans-NepetalactoneHMDB
(4AS,7S,7ar)-nepetalactoneMeSH, HMDB
Nepetalactone, (4ar-(4aalpha,7beta,7aalpha))-isomerMeSH, HMDB
Nepetalactone, (4aalpha,7alpha,7abeta)-isomerMeSH, HMDB
NepetalactoneMeSH
Chemical FormulaC10H14O2
Average Molecular Weight166.217
Monoisotopic Molecular Weight166.099379692
IUPAC Name4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-one
Traditional Namenepetalactone
CAS Registry Number17257-15-7
SMILES
CC1CCC2C1C(=O)OC=C2C
InChI Identifier
InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3
InChI KeyZDKZHVNKFOXMND-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Iridoid-skeleton
  • Bicyclic monoterpenoid
  • Monoterpenoid
  • Dihydropyranone
  • Enol ester
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot 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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014964
KNApSAcK IDC00003091
Chemspider ID83748
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92770
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.