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Showing metabocard for 2-Heptene (HMDB0061892)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:44 UTC
Update Date2022-03-07 03:17:49 UTC
HMDB IDHMDB0061892
Secondary Accession Numbers
  • HMDB61892
Metabolite Identification
Common Name2-Heptene
Description2-Heptene belongs to the class of organic compounds known as unsaturated aliphatic hydrocarbons. These are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. These compounds contain one or more double or triple bonds. Heptene is a higher olefin, or alkene with the formula C7H14. 2-Heptene is possibly neutral. It is used as an additive in lubricants, as a catalyst, and as a surfactant. The commercial product is a liquid that is a mixture of isomers.
Structure
Data?1563866243
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061892 (2-Heptene)


  Mrv0541 10081412342D          

  9  8  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0061892 (2-Heptene)

HMDB0061892
     RDKit          3D
2-Heptene
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.8647    0.0428   -0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169    0.7864    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3650    0.5471    1.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4499   -0.4636    0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8454    0.2425    0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182   -0.7579   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1051   -0.0234   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609    0.2430   -1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358   -1.0570   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8594    0.4486   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1800    1.5330    0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    1.0367    2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070   -0.9383   -0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2336   -1.2007    1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6670    1.0913   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063    0.6503    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4149   -1.1432   -1.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748   -1.5453    0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9806   -0.6737   -0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401    0.2511   -1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1370    0.9303   -0.2240 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  1  0
  6  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  7 21  1  0
M  END
Download

3D SDF for HMDB0061892 (2-Heptene)


  Mrv0541 10081412342D          

  9  8  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061892

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(C)=C(/[H])CCCC

> <INCHI_IDENTIFIER>
InChI=1S/C7H14/c1-3-5-7-6-4-2/h3,5H,4,6-7H2,1-2H3/b5-3-

> <INCHI_KEY>
OTTZHAVKAVGASB-HYXAFXHYSA-N

> <FORMULA>
C7H14

> <MOLECULAR_WEIGHT>
98.1861

> <EXACT_MASS>
98.109550448

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
13.519023030261625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-hept-2-ene

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
3.2137849009999995

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
35.1258

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-heptene (cis)

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0061892 (2-Heptene)

HMDB0061892
     RDKit          3D
2-Heptene
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.8647    0.0428   -0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169    0.7864    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3650    0.5471    1.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4499   -0.4636    0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8454    0.2425    0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182   -0.7579   -0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1051   -0.0234   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609    0.2430   -1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358   -1.0570   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8594    0.4486   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1800    1.5330    0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    1.0367    2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070   -0.9383   -0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2336   -1.2007    1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6670    1.0913   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063    0.6503    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4149   -1.1432   -1.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748   -1.5453    0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9806   -0.6737   -0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401    0.2511   -1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1370    0.9303   -0.2240 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  1  0
  6  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  7 21  1  0
M  END
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PDB for HMDB0061892 (2-Heptene)

HEADER    PROTEIN                                 08-OCT-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-14         0                                  
HETATM    1  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0       2.310   1.334   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0      -0.770   1.334   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5    8                                                  
CONECT    4    2    6                                                       
CONECT    5    3    7    9                                                  
CONECT    6    4    7                                                       
CONECT    7    5    6                                                       
CONECT    8    3                                                            
CONECT    9    5                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0061892 (2-Heptene)

COMPND    HMDB0061892
HETATM    1  C1  UNL     1      -2.865   0.043  -0.711  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.517   0.786   0.525  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.365   0.547   1.110  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.450  -0.464   0.509  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.845   0.242   0.163  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.818  -0.758  -0.459  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.105  -0.023  -0.795  1.00  0.00           C  
HETATM    8  H1  UNL     1      -2.161   0.243  -1.546  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.936  -1.057  -0.546  1.00  0.00           H  
HETATM   10  H3  UNL     1      -3.859   0.449  -1.061  1.00  0.00           H  
HETATM   11  H4  UNL     1      -3.180   1.533   0.979  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.016   1.037   2.017  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.907  -0.938  -0.369  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.234  -1.201   1.322  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.667   1.091  -0.525  1.00  0.00           H  
HETATM   16  H9  UNL     1       1.306   0.650   1.081  1.00  0.00           H  
HETATM   17  H10 UNL     1       1.415  -1.143  -1.403  1.00  0.00           H  
HETATM   18  H11 UNL     1       2.075  -1.545   0.277  1.00  0.00           H  
HETATM   19  H12 UNL     1       3.981  -0.674  -0.553  1.00  0.00           H  
HETATM   20  H13 UNL     1       3.140   0.251  -1.891  1.00  0.00           H  
HETATM   21  H14 UNL     1       3.137   0.930  -0.224  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3   11
CONECT    3    4   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7   19   20   21
END
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SMILES for HMDB0061892 (2-Heptene)

[H]\C(C)=C(/[H])CCCC
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INCHI for HMDB0061892 (2-Heptene)

InChI=1S/C7H14/c1-3-5-7-6-4-2/h3,5H,4,6-7H2,1-2H3/b5-3-
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC7H14
Average Molecular Weight98.1861
Monoisotopic Molecular Weight98.109550448
IUPAC Name(2Z)-hept-2-ene
Traditional Name2-heptene (cis)
CAS Registry NumberNot Available
SMILES
[H]\C(C)=C(/[H])CCCC
InChI Identifier
InChI=1S/C7H14/c1-3-5-7-6-4-2/h3,5H,4,6-7H2,1-2H3/b5-3-
InChI KeyOTTZHAVKAVGASB-HYXAFXHYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as unsaturated aliphatic hydrocarbons. These are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. These compounds contain one or more double or triple bonds.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassUnsaturated aliphatic hydrocarbons
Direct ParentUnsaturated aliphatic hydrocarbons
Alternative Parents
Substituents
  • Unsaturated aliphatic hydrocarbon
  • Olefin
  • Alkene
  • Acyclic olefin
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological location
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
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP3.95ALOGPS
logP3.21ChemAxon
logS-3.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.13 m³·mol⁻¹ChemAxon
Polarizability13.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.8331661259
DarkChem[M-H]-118.17331661259
DeepCCS[M+H]+131.29530932474
DeepCCS[M-H]-128.96830932474
DeepCCS[M-2H]-164.59930932474
DeepCCS[M+Na]+138.76630932474
AllCCS[M+H]+125.132859911
AllCCS[M+H-H2O]+120.632859911
AllCCS[M+NH4]+129.332859911
AllCCS[M+Na]+130.532859911
AllCCS[M-H]-132.932859911
AllCCS[M+Na-2H]-136.732859911
AllCCS[M+HCOO]-141.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Heptene[H]\C(C)=C(/[H])CCCC879.5Standard polar33892256
2-Heptene[H]\C(C)=C(/[H])CCCC711.0Standard non polar33892256
2-Heptene[H]\C(C)=C(/[H])CCCC708.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Heptene GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-4c97e980e20aab4ef8452017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Heptene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 10V, Positive-QTOFsplash10-0002-9000000000-814e429d69b303ea01552017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 20V, Positive-QTOFsplash10-0002-9000000000-4f7ca6b2a32219de65bb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 40V, Positive-QTOFsplash10-052f-9000000000-cbc4036f40e62466bb882017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 10V, Negative-QTOFsplash10-0002-9000000000-977311324da413d593d22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 20V, Negative-QTOFsplash10-0002-9000000000-31ced3983290f48b314f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 40V, Negative-QTOFsplash10-0002-9000000000-3622a90afe9fdd2dfb8b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 10V, Positive-QTOFsplash10-0a4i-9000000000-be254a819808416d534a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 20V, Positive-QTOFsplash10-0a4i-9000000000-ea9e169aed983ed50b4f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 40V, Positive-QTOFsplash10-0a4l-9000000000-1a9b86255b691c1b25932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 10V, Negative-QTOFsplash10-0002-9000000000-ab2d4bc3d9a1e9fe228e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 20V, Negative-QTOFsplash10-0002-9000000000-487be81d51c51d5b50ba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Heptene 40V, Negative-QTOFsplash10-00di-9000000000-98fd9e0931014f6f198a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHeptene
METLIN IDNot Available
PubChem Compound643836
PDB IDNot Available
ChEBI ID88413
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. Leeney TJ, Marsham PR, Ritchie GA, Senior MW: Inhibitors of prostaglandin biosynthesis: a bicyclo-(2.2.1)-heptene analogue of '2' series prostaglandins and related derivatives. Prostaglandins. 1976 Jun;11(6):953-60. [PubMed:819968 ]
  2. Weinshenker NM: Improved preparation of a prostaglandin intermediate; 2-chloro-2-cyano- 5-7-syn-methoxymethyl bicyclo (2.2.1) heptene. Prostaglandins. 1973 Feb;3(2):219-22. [PubMed:4729570 ]
  3. Jean Lahouste, Maurice Lemattre, Jean-Claude Muller, Claude Stein, 'Process for manufacturing polymers of bicyclo [2.2.1] heptene-2 and its substitution derivatives.' U.S. Patent US4020021, issued September, 1971. [Link]
  4. Burton A. Christensen, Robert B. Morin, Edward Walton, '3-(.bet a.-Hydroxyethylidene)-6-(.alpha.-Hydroxyethyl)-7-oxo-4-oxaazabicyclo[3.2. 0]heptene-2-carboxylic acid and derivatives thereof.' U.S. Patent US4076826, issued April, 1976. [Link]
  5. Maurizio Foglio, Antonino Suarato, Paolo Masi, Giovanni Franceschi, Giorgio Palamidessi, Luigi Bernardi, U.S. Patent US4077970, issued December, 1975. [Link]
  6. Claude Stein, Patrick Le Delliou, 'Method of cold-shaping of mixtures comprising poly[2.2.1]bicyclo-2-heptene or its short-chain.' U.S. Patent US4137210, issued May, 1971. [Link]
  7. Maurizio Foglio, Antonino Suarato, Paolo Masi, Giovanni Franceschi, Giorgio Palamidessi, Luigi Bernardi, 'Process for the production of substituted 4-thia-2,6-diaza[3.2.0]-2-heptene-7-one.' U.S. Patent US4155911, issued May 22, 1979. [Link]
  8. Tsuneo Kanamaru, Susumu Shinagawa, Masayuki Muroi, '2-oxo-5-methyl-6-[4-heptene]-2H-pyrano[3,2-c]pyridine.' U.S. Patent US4803275, issued February 07, 1989. [Link]
  9. Dariush Davalian, Cheng-I Lin, Edwin F. Ullman, '2-methyl-4-hexene- and 2-methyl-4-heptene-1,2-diol derivatives.' U.S. Patent US5089390, issued February, 1988. [Link]
  10. Dariush Davalian, Cheng-I Lin, Edwin F. Ullman, '2-methyl-4-hexene-and 3-methyl-5-heptene-1,2-diol derivatives.' U.S. Patent US5401649, issued September, 1988. [Link]