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Showing NP-Card for (5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane (NP0230623)

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Record Information
Version2.0
Created at2022-09-06 11:07:46 UTC
Updated at2022-09-06 11:07:46 UTC
NP-MRD IDNP0230623
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane
Description(5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]Hexane belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane is found in Achillea abrotanoides, Achillea millefolium, Ageratum conyzoides, Aloysia citrodora, Aloysia gratissima, Alpinia zerumbet, Artemisia annua, Artemisia herba-alba, Artemisia thuscula, Artemisia vulgaris, Athamanta macedonica, Bellis perennis, Chamaecyparis obtusa, Chromolaena odorata, Citrus reticulata, Citrus sinensis, Cuminum cyminum, Cyclotrichium niveum, Eucalyptus dealbata, Juniperus monticola, Lepechinia chamaedryoides, Liquidambar styraciflua, Melaleuca alternifolia, Mentha arvensis, Micromeria biflora, Micromeria myrtifolia, Nepeta nuda, Nepeta racemosa, Ocimum americanum, Ocimum gratissimum, Origanum acutidens, Origanum hypericifolium, Origanum majorana, Origanum minutiflorum, Origanum ramonense, Origanum sipyleum, Origanum syriacum, Origanum vulgare, Pimenta racemosa, Piper auritum, Pycnanthemum floridanum, Salvia absconditiflora, Salvia caespitosa, Salvia fruticosa, Santolina chamaecyparissus, Thymbra capitata, Thymbra spicata, Thymus eigii, Thymus longicaulis, Thymus saturejoides, Thymus vulgaris, Thymus zygioides, Trachyspermum ammi and Vitex negundo. Based on a literature review very few articles have been published on (5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]Hexane.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0230623 ((5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane)


  Mrv1652309062213072D          

 10 11  0  0  1  0            999 V2000
    2.4975    2.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224   -0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073   -0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    1.2987    0.0000 C   0  0  1  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
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
 10  9  1  1  0  0  0
  2 10  1  0  0  0  0
  5 10  1  0  0  0  0
M  END
Download

3D MOL for NP0230623 ((5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.4397   -0.3693   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -0.4876   -0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355   -1.5127    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   -0.7057    0.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1003    0.3221   -0.0807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4307    0.3670   -0.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2888    1.4369   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1847   -0.9389   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6931    1.5731   -0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1752    0.3730   -0.8384 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9259    0.4276   -0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0948   -1.0379    0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8515   -1.9523    1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289   -2.3326   -0.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302   -1.4021    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2974   -0.2212    1.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    0.5957   -1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0907    2.4172   -0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9930    1.3766    1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    1.1366   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6115   -0.9427    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5911   -1.8188   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0717   -0.9289   -1.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3361    2.3993   -0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2716    1.9086    0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006    0.3169   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  5  6  1  6
  5  9  1  0
  9 10  1  0
 10  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 10  5  1  0
  4  5  1  0
  7 18  1  0
  7 19  1  0
  7 20  1  0
  6 17  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  6
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
M  END
Download

3D SDF for NP0230623 ((5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane)


  Mrv1652309062213072D          

 10 11  0  0  1  0            999 V2000
    2.4975    2.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224   -0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073   -0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    1.2987    0.0000 C   0  0  1  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
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
 10  9  1  1  0  0  0
  2 10  1  0  0  0  0
  5 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230623

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C12C[C@H]1C(=C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3/t9-,10?/m0/s1

> <INCHI_KEY>
NDVASEGYNIMXJL-RGURZIINSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.250722224102113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexane

> <JCHEM_LOGP>
2.859595116666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
43.6498

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0230623 ((5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane)

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PDB for NP0230623 ((5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane)
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       4.662   4.365   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.186   2.900   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.091   1.654   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.186   0.408   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.721   0.884   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.095  -0.523   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.000  -1.768   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.563  -0.684   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.388   1.654   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.721   2.424   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9   10                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0230623 ((5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane)
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SMILES for NP0230623 ((5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane)
CC(C)C12C[C@H]1C(=C)CC2
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INCHI for NP0230623 ((5s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane)
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3/t9-,10?/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H16
Average Mass136.2380 Da
Monoisotopic Mass136.12520 Da
IUPAC Name(5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexane
Traditional Name(5S)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexane
CAS Registry NumberNot Available
SMILES
CC(C)C12C[C@H]1C(=C)CC2
InChI Identifier
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3/t9-,10?/m0/s1
InChI KeyNDVASEGYNIMXJL-RGURZIINSA-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
Achillea abrotanoidesLOTUS Database
Achillea millefoliumLOTUS Database
Ageratum conyzoidesLOTUS Database
Aloysia citrodoraLOTUS Database
Aloysia gratissimaLOTUS Database
Alpinia zerumbetLOTUS Database
Artemisia annuaLOTUS Database
Artemisia herba-albaLOTUS Database
Artemisia thusculaLOTUS Database
Artemisia vulgarisLOTUS Database
Athamanta macedonicaLOTUS Database
Bellis perennisLOTUS Database
Chamaecyparis obtusaLOTUS Database
Chromolaena odorataLOTUS Database
Citrus reticulataLOTUS Database
Citrus sinensisLOTUS Database
Cuminum cyminumLOTUS Database
Cyclotrichium niveumLOTUS Database
Eucalyptus dealbataLOTUS Database
Juniperus monticolaLOTUS Database
Lepechinia chamaedryoidesLOTUS Database
Liquidambar styracifluaLOTUS Database
Melaleuca alternifoliaLOTUS Database
Mentha arvensisLOTUS Database
Micromeria bifloraLOTUS Database
Micromeria myrtifoliaLOTUS Database
Nepeta nudaLOTUS Database
Nepeta racemosaLOTUS Database
Ocimum americanumLOTUS Database
Ocimum gratissimumLOTUS Database
Origanum acutidensLOTUS Database
Origanum hypericifoliumLOTUS Database
Origanum majoranaLOTUS Database
Origanum minutiflorumLOTUS Database
Origanum ramonenseLOTUS Database
Origanum sipyleumLOTUS Database
Origanum syriacumLOTUS Database
Origanum vulgareLOTUS Database
Pimenta racemosaLOTUS Database
Piper auritumLOTUS Database
Pycnanthemum floridanumLOTUS Database
Salvia absconditifloraLOTUS Database
Salvia caespitosaLOTUS Database
Salvia fruticosaLOTUS Database
Santolina chamaecyparissusLOTUS Database
Thymbra capitataLOTUS Database
Thymbra spicataLOTUS Database
Thymus eigiiLOTUS Database
Thymus longicaulisLOTUS Database
Thymus satureioidesLOTUS Database
Thymus vulgarisLOTUS Database
Thymus zygioidesLOTUS Database
Trachyspermum ammiLOTUS Database
Vitex negundoLOTUS 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
    • 

  • Thujane 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
logP2.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.65 m³·mol⁻¹ChemAxon
Polarizability17.25 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 ID4934637  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6429260  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]