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Showing NP-Card for 1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one (NP0192344)

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Record Information
Version2.0
Created at2022-09-04 09:31:58 UTC
Updated at2022-09-04 09:31:58 UTC
NP-MRD IDNP0192344
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one
Description13-Nor-Opposit-4(15)-en-11-one belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. 1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one is found in Chrysopogon zizanioides. Based on a literature review very few articles have been published on 13-nor-Opposit-4(15)-en-11-one.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0192344 (1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one)


  Mrv1652309042211312D          

 15 16  0  0  1  0            999 V2000
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    3.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    2.3061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  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  1  0  0  0
  6  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
  2 15  1  0  0  0  0
  6 15  1  0  0  0  0
M  END
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3D MOL for NP0192344 (1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one)

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3D SDF for NP0192344 (1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one)

  Mrv1652309042211312D          

 15 16  0  0  1  0            999 V2000
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    3.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    2.3061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  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  1  0  0  0
  6  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
  2 15  1  0  0  0  0
  6 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192344

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC1CC[C@@]2(C)CCCC(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O/c1-10-5-4-7-14(3)8-6-12(13(10)14)9-11(2)15/h12-13H,1,4-9H2,2-3H3/t12?,13?,14-/m1/s1

> <INCHI_KEY>
LTLLRSRCWUAIJT-JXQTWKCFSA-N

> <FORMULA>
C14H22O

> <MOLECULAR_WEIGHT>
206.329

> <EXACT_MASS>
206.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
24.8312367074377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(3aR)-3a-methyl-7-methylidene-octahydro-1H-inden-1-yl]propan-2-one

> <JCHEM_LOGP>
3.202684869333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.5993209351007

> <JCHEM_PKA_STRONGEST_BASIC>
-7.277597678889142

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
62.6693

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(3aR)-3a-methyl-7-methylidene-hexahydro-1H-inden-1-yl]propan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0192344 (1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one)
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PDB for NP0192344 (1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.626  -1.532   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.877   4.625   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.401   6.090   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.383   4.305   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0192344 (1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one)
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SMILES for NP0192344 (1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one)
CC(=O)CC1CC[C@@]2(C)CCCC(=C)C12
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INCHI for NP0192344 (1-[(3ar)-3a-methyl-7-methylidene-hexahydro-1h-inden-1-yl]propan-2-one)
InChI=1S/C14H22O/c1-10-5-4-7-14(3)8-6-12(13(10)14)9-11(2)15/h12-13H,1,4-9H2,2-3H3/t12?,13?,14-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC14H22O
Average Mass206.3290 Da
Monoisotopic Mass206.16707 Da
IUPAC Name1-[(3aR)-3a-methyl-7-methylidene-octahydro-1H-inden-1-yl]propan-2-one
Traditional Name1-[(3aR)-3a-methyl-7-methylidene-hexahydro-1H-inden-1-yl]propan-2-one
CAS Registry NumberNot Available
SMILES
CC(=O)CC1CC[C@@]2(C)CCCC(=C)C12
InChI Identifier
InChI=1S/C14H22O/c1-10-5-4-7-14(3)8-6-12(13(10)14)9-11(2)15/h12-13H,1,4-9H2,2-3H3/t12?,13?,14-/m1/s1
InChI KeyLTLLRSRCWUAIJT-JXQTWKCFSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Vetiveria zizanioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentIridoids and derivatives  
Alternative Parents
Substituents
  • 11-noriridane monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Ketone
    • 

  • 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
logP3.2ChemAxon
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.67 m³·mol⁻¹ChemAxon
Polarizability24.83 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91747153  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]