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Showing NP-Card for methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate (NP0272017)

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Record Information
Version2.0
Created at2022-09-08 18:29:43 UTC
Updated at2022-09-08 18:29:44 UTC
NP-MRD IDNP0272017
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate
DescriptionMethyl isonuapauanoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate is found in Diacarnus bismarckensis and Negombata corticata. Methyl isonuapauanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0272017 (methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate)


  Mrv1533004241516042D          

 24 25  0  0  0  0            999 V2000
    1.9592   -6.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -5.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -5.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -4.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -4.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -5.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -3.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -3.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4895   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377   -0.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4555    0.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6430    0.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858    1.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7983    1.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804    0.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5501   -0.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1632   -0.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4353   -1.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -2.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -3.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
M  END
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3D MOL for NP0272017 (methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate)

Download
3D SDF for NP0272017 (methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate)

  Mrv1533004241516042D          

 24 25  0  0  0  0            999 V2000
    1.9592   -6.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -5.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -5.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -4.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -4.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -5.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -3.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -3.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4895   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377   -0.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4555    0.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6430    0.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858    1.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7983    1.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804    0.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5501   -0.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1632   -0.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4353   -1.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -2.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -3.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(C)C1CCC(C)(CCC2C(=C)CCCC2(C)C)OO1

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O4/c1-14-8-7-11-19(3,4)16(14)9-12-20(5)13-10-17(23-24-20)15(2)18(21)22-6/h15-17H,1,7-13H2,2-6H3

> <INCHI_KEY>
MYBJZJMUOIRKIX-UHFFFAOYSA-N

> <FORMULA>
C20H34O4

> <MOLECULAR_WEIGHT>
338.488

> <EXACT_MASS>
338.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.316987318177894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate

> <ALOGPS_LOGP>
5.34

> <JCHEM_LOGP>
4.970410055333334

> <ALOGPS_LOGS>
-5.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.836291214937567

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
94.1148

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0272017 (methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate)
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PDB for NP0272017 (methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       3.657 -11.960   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.991 -11.190   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.991  -9.650   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.325  -8.880   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.657  -8.880   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.324  -9.650   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.657  -7.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.324  -6.570   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.324  -5.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.647  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.120  -1.633   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.110  -0.453   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.584   0.994   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.067   1.261   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.574   2.174   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.090   1.906   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.617   0.459   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.627  -0.721   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.771  -1.751   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.413  -2.246   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.991  -5.030   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.991  -6.570   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   23                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   10   24                                                       
CONECT   24   23    7                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

Download
3D PDB for NP0272017 (methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate)
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SMILES for NP0272017 (methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate)
COC(=O)C(C)C1CCC(C)(CCC2C(=C)CCCC2(C)C)OO1
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INCHI for NP0272017 (methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate)
InChI=1S/C20H34O4/c1-14-8-7-11-19(3,4)16(14)9-12-20(5)13-10-17(23-24-20)15(2)18(21)22-6/h15-17H,1,7-13H2,2-6H3
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View in JSmol
Synonyms
ValueSource
Methyl isonuapauanoic acidGenerator
Methyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoic acidGenerator
Chemical FormulaC20H34O4
Average Mass338.4880 Da
Monoisotopic Mass338.24571 Da
IUPAC Namemethyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate
Traditional Namemethyl 2-{6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyl-1,2-dioxan-3-yl}propanoate
CAS Registry NumberNot Available
SMILES
COC(=O)C(C)C1CCC(C)(CCC2C(=C)CCCC2(C)C)OO1
InChI Identifier
InChI=1S/C20H34O4/c1-14-8-7-11-19(3,4)16(14)9-12-20(5)13-10-17(23-24-20)15(2)18(21)22-6/h15-17H,1,7-13H2,2-6H3
InChI KeyMYBJZJMUOIRKIX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Diacarnus bismarckensisLOTUS Database
Negombata corticataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquiterpenoid
    • 

  • Megastigmane sesquiterpenoid
    • 

  • Cyclofarsesane sesquiterpenoid
    • 

  • Ortho-dioxane
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Dialkyl peroxide
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP5.34ALOGPS
logP4.97ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.11 m³·mol⁻¹ChemAxon
Polarizability39.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound387914  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]