Np mrd loader

Showing NP-Card for 1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane (NP0239359)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-06 22:56:19 UTC
Updated at2022-09-06 22:56:19 UTC
NP-MRD IDNP0239359
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane
Description2-Methylenebornane belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane is found in Aspergillus candidus and Chrysanthemum morifolium. 1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane was first documented in 2017 (PMID: 28246382). Based on a literature review a small amount of articles have been published on 2-Methylenebornane (PMID: 34964253) (PMID: 32364702) (PMID: 29672609).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0239359 (1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane)


  Mrv1652309072200562D          

 11 12  0  0  0  0            999 V2000
   -0.1565    1.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2733    0.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543   -0.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -0.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709   -0.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899    0.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850    0.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812    1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599    0.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3133    0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2880   -0.2873    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0239359 (1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane)

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.4131    1.1403   -0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    0.3621   -0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8023   -0.5701   -1.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219   -1.0350   -1.0158 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2372   -2.0535    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5206   -1.2191    1.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303    0.2052    0.6229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5057    1.2342    1.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9032    0.1686   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0413    1.3549   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595   -0.1142    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6705    1.7561    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9698    1.1214   -1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5068   -1.4476   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414   -0.1296   -2.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2660   -1.2969   -1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074   -2.8419   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439   -2.4940    0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206   -1.3851    2.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5742   -1.5345    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412    1.4740    1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762    2.1293    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235    0.8698    2.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8255    1.1139   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2955    2.2700   -0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0952    1.4675   -1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8674   -0.5802    0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7673   -0.8063    1.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4793    0.8404    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9 11  1  0
  9  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  2  1  0
  2  1  2  3
  2  3  1  0
  7  9  1  0
  3  4  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
  4 16  1  6
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
M  END
Download

3D SDF for NP0239359 (1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane)


  Mrv1652309072200562D          

 11 12  0  0  0  0            999 V2000
   -0.1565    1.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2733    0.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543   -0.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -0.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709   -0.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899    0.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850    0.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812    1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599    0.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3133    0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2880   -0.2873    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239359

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CCC1(C)C(=C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H18/c1-8-7-9-5-6-11(8,4)10(9,2)3/h9H,1,5-7H2,2-4H3

> <INCHI_KEY>
ZASFWGOMAIPHLN-UHFFFAOYSA-N

> <FORMULA>
C11H18

> <MOLECULAR_WEIGHT>
150.265

> <EXACT_MASS>
150.14085058

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
18.836843194829477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane

> <JCHEM_LOGP>
3.1596422366666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
48.1249

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0239359 (1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane)

Download
PDB for NP0239359 (1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.292   2.537   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.510   1.053   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.475  -0.487   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.581  -1.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.932  -0.487   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.968   1.053   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.652   1.853   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.018   3.419   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.232   0.322   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.585   0.829   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.538  -0.536   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7    4   10   11                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0239359 (1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane)
Download
SMILES for NP0239359 (1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane)
CC1(C)C2CCC1(C)C(=C)C2
Download
INCHI for NP0239359 (1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane)
InChI=1S/C11H18/c1-8-7-9-5-6-11(8,4)10(9,2)3/h9H,1,5-7H2,2-4H3
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC11H18
Average Mass150.2650 Da
Monoisotopic Mass150.14085 Da
IUPAC Name1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane
Traditional Name1,7,7-trimethyl-2-methylidenebicyclo[2.2.1]heptane
CAS Registry NumberNot Available
SMILES
CC1(C)C2CCC1(C)C(=C)C2
InChI Identifier
InChI=1S/C11H18/c1-8-7-9-5-6-11(8,4)10(9,2)3/h9H,1,5-7H2,2-4H3
InChI KeyZASFWGOMAIPHLN-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
Aspergillus candidusLOTUS Database
Chrysanthemum morifoliumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
    • 

  • Bornane monoterpenoid
    • 

  • Branched unsaturated hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.12 m³·mol⁻¹ChemAxon
Polarizability18.84 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID110022  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound123425  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Drummond L, von Wallbrunn C, Buchhaupt M: Microbial Degradation of 2-Methylisoborneol in Forest Soil. Chem Biodivers. 2022 Feb;19(2):e202100734. doi: 10.1002/cbdv.202100734. Epub 2021  Dec 29. [PubMed:34964253  ] 
  2. Chou WK, Gould CA, Cane DE: Incubation of 2-methylisoborneol synthase with the intermediate analog 2-methylneryl diphosphate. J Antibiot (Tokyo). 2017 May;70(5):625-631. doi: 10.1038/ja.2017.24. Epub 2017  Mar 1. [PubMed:28246382  ] 
  3. Kschowak MJ, Maier F, Wortmann H, Buchhaupt M: Analyzing and Engineering the Product Selectivity of a 2-Methylenebornane Synthase. ACS Synth Biol. 2020 May 15;9(5):981-986. doi: 10.1021/acssynbio.9b00432. Epub  2020 May 4. [PubMed:32364702  ] 
  4. Kschowak MJ, Wortmann H, Dickschat JS, Schrader J, Buchhaupt M: Heterologous expression of 2-methylisoborneol / 2 methylenebornane biosynthesis genes in Escherichia coli yields novel C11-terpenes. PLoS One. 2018 Apr 19;13(4):e0196082. doi: 10.1371/journal.pone.0196082.  eCollection 2018. [PubMed:29672609  ] 
  5. LOTUS database [Link]