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Showing NP-Card for (1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid (NP0225441)

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Record Information
Version2.0
Created at2022-09-06 04:09:50 UTC
Updated at2022-09-06 04:09:50 UTC
NP-MRD IDNP0225441
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid
DescriptionChaminic acid, also known as chaminate or CRN-10-COOH, 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-3-ene-3-carboxylic acid is found in Calocedrus formosana. (1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid was first documented in 2015 (PMID: 24819613). Based on a literature review very few articles have been published on Chaminic acid (PMID: 35009066).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0225441 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid)


  Mrv1652309062206092D          

 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  1  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  2  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
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3D MOL for NP0225441 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

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3D SDF for NP0225441 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

  Mrv1652309062206092D          

 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  1  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  2  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>
NP0225441

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2CC=C(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/h3,7-8H,4-5H2,1-2H3,(H,11,12)/t7-,8+/m1/s1

> <INCHI_KEY>
CKSIWMCJGLFKSZ-SFYZADRCSA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.22

> <EXACT_MASS>
166.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.390342570766435

> <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-3-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>
4.852002032025706

> <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-3-ene-3-carboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0225441 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid)
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PDB for NP0225441 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid)
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       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 NP0225441 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid)
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SMILES for NP0225441 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid)
CC1(C)[C@@H]2CC=C(C[C@H]12)C(O)=O
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INCHI for NP0225441 ((1s,6r)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid)
InChI=1S/C10H14O2/c1-10(2)7-4-3-6(9(11)12)5-8(7)10/h3,7-8H,4-5H2,1-2H3,(H,11,12)/t7-,8+/m1/s1
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View in JSmol
Synonyms
ValueSource
ChaminateGenerator
CRN-10-COOHMeSH
delta3-Caren-10-carboxylic acidMeSH
Chemical FormulaC10H14O2
Average Mass166.2200 Da
Monoisotopic Mass166.09938 Da
IUPAC Name(1S,6R)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid
Traditional Name(1S,6R)-7,7-dimethylbicyclo[4.1.0]hept-3-ene-3-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1(C)[C@@H]2CC=C(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/h3,7-8H,4-5H2,1-2H3,(H,11,12)/t7-,8+/m1/s1
InChI KeyCKSIWMCJGLFKSZ-SFYZADRCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Calocedrus formosanaLOTUS 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
logP1.99ChemAxon
pKa (Strongest Acidic)4.85ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.44 m³·mol⁻¹ChemAxon
Polarizability18.39 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00011046  
Chemspider ID61591061  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound90472689  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hsiao WW, Kumar KJS, Lee HJ, Tsao NW, Wang SY: Anti-Melanogenic Activity of Calocedrus formosana Wood Essential Oil and Its Chemical Composition Analysis. Plants (Basel). 2021 Dec 25;11(1):62. doi: 10.3390/plants11010062. [PubMed:35009066  ] 
  2. Schmidt L, Belov VN, Goen T: Human metabolism of Delta3-carene and renal elimination of Delta3-caren-10-carboxylic acid (chaminic acid) after oral administration. Arch Toxicol. 2015 Mar;89(3):381-92. doi: 10.1007/s00204-014-1251-5. Epub 2014  May 14. [PubMed:24819613  ] 
  3. LOTUS database [Link]