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Showing NP-Card for 3-methylidenecyclopent-1-ene (NP0234909)

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Record Information
Version1.0
Created at2022-09-06 17:14:51 UTC
Updated at2022-09-06 17:14:52 UTC
NP-MRD IDNP0234909
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-methylidenecyclopent-1-ene
Description3-Methylenecyclopentene belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. 3-methylidenecyclopent-1-ene is found in Artemisia argyi. It was first documented in 2009 (PMID: 19456157). Based on a literature review a small amount of articles have been published on 3-Methylenecyclopentene (PMID: 28328182) (PMID: 22651220).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0234909 (3-methylidenecyclopent-1-ene)


  Mrv1652309062219142D          

  6  6  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
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3D MOL for NP0234909 (3-methylidenecyclopent-1-ene)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    2.0608    0.1853    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069    0.1672    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0974    1.2733   -0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3459    0.8491   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873   -0.5884    0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -1.0514   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174    1.1625    0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959   -0.7177    0.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2722    2.2833   -0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2072    1.4560   -0.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437   -0.6660    1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -1.1217   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337   -1.9050    0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1508   -1.3265   -1.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  1  7  1  0
  1  8  1  0
  6 13  1  0
  6 14  1  0
  5 11  1  0
  5 12  1  0
  4 10  1  0
  3  9  1  0
M  END
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3D SDF for NP0234909 (3-methylidenecyclopent-1-ene)


  Mrv1652309062219142D          

  6  6  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234909

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C=C1CCC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8/c1-6-4-2-3-5-6/h2,4H,1,3,5H2

> <INCHI_KEY>
YWQLRBQGXHZJCF-UHFFFAOYSA-N

> <FORMULA>
C6H8

> <MOLECULAR_WEIGHT>
80.13

> <EXACT_MASS>
80.062600258

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.688832714050971

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylidenecyclopent-1-ene

> <JCHEM_LOGP>
1.8002949536666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
28.447699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-methylidenecyclopent-1-ene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0234909 (3-methylidenecyclopent-1-ene)

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PDB for NP0234909 (3-methylidenecyclopent-1-ene)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END

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3D PDB for NP0234909 (3-methylidenecyclopent-1-ene)
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SMILES for NP0234909 (3-methylidenecyclopent-1-ene)
C=C1CCC=C1
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INCHI for NP0234909 (3-methylidenecyclopent-1-ene)
InChI=1S/C6H8/c1-6-4-2-3-5-6/h2,4H,1,3,5H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC6H8
Average Mass80.1300 Da
Monoisotopic Mass80.06260 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
C=C1CCC=C1
InChI Identifier
InChI=1S/C6H8/c1-6-4-2-3-5-6/h2,4H,1,3,5H2
InChI KeyYWQLRBQGXHZJCF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia argyiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.
KingdomOrganic compounds  
Super ClassHydrocarbons  
ClassUnsaturated hydrocarbons  
Sub ClassBranched unsaturated hydrocarbons  
Direct ParentBranched unsaturated hydrocarbons  
Alternative Parents
Substituents
  • Branched unsaturated hydrocarbon
    • 

  • Cycloalkene
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Olefin
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID120482  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound136723  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Liu B, Li S, Wang M, Cui D: Coordination Polymerization of Renewable 3-Methylenecyclopentene with Rare-Earth-Metal Precursors. Angew Chem Int Ed Engl. 2017 Apr 10;56(16):4560-4564. doi:  10.1002/anie.201700546. Epub 2017 Mar 22. [PubMed:28328182  ] 
  2. Bozkaya U, Ozkan I: Thermal aromatizations of 2-vinylmethylenecyclopropane and 3-vinylcyclobutene. J Org Chem. 2012 Jul 6;77(13):5714-23. doi: 10.1021/jo300877w. Epub 2012 Jun 7. [PubMed:22651220  ] 
  3. Kobayashi S, Lu C, Hoye TR, Hillmyer MA: Controlled polymerization of a cyclic diene prepared from the ring-closing metathesis of a naturally occurring monoterpene. J Am Chem Soc. 2009 Jun 17;131(23):7960-1. doi: 10.1021/ja9027567. [PubMed:19456157  ] 
  4. LOTUS database [Link]