Showing NP-Card for myrtenic acid (NP0183250)

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Record Information
Version2.0
Created at2022-09-03 22:07:47 UTC
Updated at2022-09-03 22:07:47 UTC
NP-MRD IDNP0183250
Secondary Accession NumbersNone
Natural Product Identification
Common Namemyrtenic acid
DescriptionMyrtenic acid, also known as myrtenoate, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. myrtenic acid is found in Chamaecyparis formosensis. myrtenic acid was first documented in 1980 (PMID: 7385912). Myrtenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 26679931) (PMID: 26996011) (PMID: 29575869).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0183250 (myrtenic acid)

Myrtenic acid
  Mrv1572001071617232D          

 12 13  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  4  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  3  1  0  0  0  0
  7  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  5  2  0  0  0  0
  3 10  1  0  0  0  0
  2 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  2  0  0  0  0
M  END
Download

3D MOL for NP0183250 (myrtenic acid)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -1.2441    1.2223    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130   -0.1201    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443   -1.0345    0.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8408   -0.0888   -1.2352 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0983    1.0202   -1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3095    0.9728   -0.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3642    0.0839    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4627   -0.0651    1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4537   -0.9335    2.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5809    0.7544    1.1007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040   -0.8242    0.4126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0257   -1.3652   -1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629    1.1910    1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2950    1.5550    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    2.0008    0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8707   -1.7405    1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5843   -1.6739   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837   -0.4801    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6884   -0.1930   -1.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681    2.0154   -1.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626    0.8647   -2.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1082    1.6775   -0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4354    0.4769    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2684   -1.5911    1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857   -1.4422   -1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150   -2.2825   -0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4 12  1  0
 12 11  1  0
 11  7  1  0
  7  6  2  0
  6  5  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
 11  2  1  0
  5  4  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
  4 19  1  6
 12 25  1  0
 12 26  1  0
 11 24  1  1
  6 22  1  0
  5 20  1  0
  5 21  1  0
 10 23  1  0
M  END
Download

3D SDF for NP0183250 (myrtenic acid)

Myrtenic acid
  Mrv1572001071617232D          

 12 13  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  4  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  3  1  0  0  0  0
  7  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  5  2  0  0  0  0
  3 10  1  0  0  0  0
  2 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0183250

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CC1C(=CC2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O2/c1-10(2)6-3-4-7(9(11)12)8(10)5-6/h4,6,8H,3,5H2,1-2H3,(H,11,12)

> <INCHI_KEY>
XPHVDOXZJRTIMV-UHFFFAOYSA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.22

> <EXACT_MASS>
166.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.24439621981654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
1.9933540453333336

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.8419393221697336

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
46.4395

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
myrtenic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0183250 (myrtenic acid)

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PDB for NP0183250 (myrtenic acid)
HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Myrtenic acid                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    4   10                                                  
CONECT    3    4    5   10                                                  
CONECT    4    3    2    8    9                                             
CONECT    5    3    7    6                                                  
CONECT    6    1    5                                                       
CONECT    7    5   11   12                                                  
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    3    2                                                       
CONECT   11    7                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0183250 (myrtenic acid)
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SMILES for NP0183250 (myrtenic acid)
CC1(C)C2CC1C(=CC2)C(O)=O
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INCHI for NP0183250 (myrtenic acid)
InChI=1S/C10H14O2/c1-10(2)6-3-4-7(9(11)12)8(10)5-6/h4,6,8H,3,5H2,1-2H3,(H,11,12)
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View in JSmol
Synonyms
ValueSource
Myrtenoic acidChEBI
6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylic acidKegg
MyrtenoateGenerator
6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylateGenerator
MyrtenateGenerator
Chemical FormulaC10H14O2
Average Mass166.2200 Da
Monoisotopic Mass166.09938 Da
IUPAC Name6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylic acid
Traditional Namemyrtenic acid
CAS Registry NumberNot Available
SMILES
CC1(C)C2CC1C(=CC2)C(O)=O
InChI Identifier
InChI=1S/C10H14O2/c1-10(2)6-3-4-7(9(11)12)8(10)5-6/h4,6,8H,3,5H2,1-2H3,(H,11,12)
InChI KeyXPHVDOXZJRTIMV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Chamaecyparis formosensisLOTUS 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
  • Pinane 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 Descriptors
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
logP2.49ALOGPS
logP1.99ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.44 m³·mol⁻¹ChemAxon
Polarizability18.24 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 IDC00011042  
Chemspider IDNot Available
KEGG Compound IDC11940  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound86840  
PDB IDNot Available
ChEBI ID25459  
Good Scents IDNot Available
References
General References
  1. Schmidt L, Goen T: Human metabolism of alpha-pinene and metabolite kinetics after oral administration. Arch Toxicol. 2017 Feb;91(2):677-687. doi: 10.1007/s00204-015-1656-9. Epub 2015  Dec 17. [PubMed:26679931  ] 
  2. Dosoky NS, Moriarity DM, Setzer WN: Phytochemical and Biological Investigations of Conradina canescens. Nat Prod Commun. 2016 Jan;11(1):25-8. [PubMed:26996011  ] 
  3. Turgumbayeva AA, Ustenova GO, Yeskalieva BK, Ramazanova BA, Rahimov KD, Aisa H, Juszkiewicz KT: Volatile oil composition of Carthamus Tinctorius L. flowers grown in Kazakhstan. Ann Agric Environ Med. 2018 Mar 14;25(1):87-89. doi: 10.5604/12321966.1235170.  Epub 2017 Feb 11. [PubMed:29575869  ] 
  4. Southwell IA, Flynn TM, Degabriele R: Metabolism of alpha- and beta-pinene, p-cymene and 1,8-cineole in the brushtail possum, Trichosurus vulpecula. Xenobiotica. 1980 Jan;10(1):17-23. doi: 10.3109/00498258009033726. [PubMed:7385912  ] 
  5. LOTUS database [Link]