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Showing NP-Card for (1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid (NP0328750)

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Record Information
Version2.0
Created at2022-09-12 12:30:56 UTC
Updated at2022-09-12 12:30:56 UTC
NP-MRD IDNP0328750
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid
Description(-)-Isochaminic acid belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid is found in Bridelia retusa. Based on a literature review very few articles have been published on (-)-Isochaminic acid.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0328750 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid)


  Mrv1652309122214302D          

 12 13  0  0  1  0            999 V2000
    0.1842    0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
  4 12  1  0  0  0  0
  2 12  1  0  0  0  0
M  END
Download

3D MOL for NP0328750 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -2.9182   -0.1103   -0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5316    0.0417   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4502    1.0837    0.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237   -0.1072   -1.1081 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9183    0.6092   -0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8384    0.0824    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0448    0.7948    0.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9178    0.2812    1.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2508    2.0874   -0.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6274   -1.3059    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823   -1.4533    0.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7196   -1.1885   -0.2051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8521   -0.6979   -1.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4347    0.8576   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497   -0.7317   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4053    1.3744    1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641    2.0174    0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8979    0.7234    1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5370   -0.1516   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0263    1.6282   -1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8424    2.8942    0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2652   -1.4908    1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8014   -1.9830   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028   -2.4409    1.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0029   -0.7068    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -2.1078   -0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 12  1  0
 12 11  1  0
 11 10  1  0
 10  6  1  0
  6  5  2  0
  5  4  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  4  2  1  0
  4 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
 12 26  1  6
 11 24  1  0
 11 25  1  0
 10 22  1  0
 10 23  1  0
  5 20  1  0
  4 19  1  6
  9 21  1  0
M  END
Download

3D SDF for NP0328750 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid)


  Mrv1652309122214302D          

 12 13  0  0  1  0            999 V2000
    0.1842    0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
  4 12  1  0  0  0  0
  2 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2CCC(=C[C@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O2/c1-10(2)7-4-3-6(9(11)12)5-8(7)10/h5,7-8H,3-4H2,1-2H3,(H,11,12)/t7-,8+/m1/s1

> <INCHI_KEY>
BKLAIYZBALVMQV-SFYZADRCSA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.22

> <EXACT_MASS>
166.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.34370480253418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6R)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid

> <JCHEM_LOGP>
1.9933540453333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.851377991181794

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
46.4395

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0328750 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid)

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PDB for NP0328750 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.344   0.410   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344  -1.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   12                                             
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    4    2                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0328750 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid)
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SMILES for NP0328750 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid)
CC1(C)[C@@H]2CCC(=C[C@H]12)C(O)=O
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INCHI for NP0328750 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxylic acid)
InChI=1S/C10H14O2/c1-10(2)7-4-3-6(9(11)12)5-8(7)10/h5,7-8H,3-4H2,1-2H3,(H,11,12)/t7-,8+/m1/s1
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View in JSmol
Synonyms
ValueSource
(-)-IsochaminateGenerator
Chemical FormulaC10H14O2
Average Mass166.2200 Da
Monoisotopic Mass166.09938 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC1(C)[C@@H]2CCC(=C[C@H]12)C(O)=O
InChI Identifier
InChI=1S/C10H14O2/c1-10(2)7-4-3-6(9(11)12)5-8(7)10/h5,7-8H,3-4H2,1-2H3,(H,11,12)/t7-,8+/m1/s1
InChI KeyBKLAIYZBALVMQV-SFYZADRCSA-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
Bridelia retusaLOTUS 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
  • Carane monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00036246  
Chemspider ID555055  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound639640  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]