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Showing NP-Card for (3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one (NP0301986)

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Record Information
Version2.0
Created at2022-09-10 15:15:54 UTC
Updated at2022-09-10 15:15:54 UTC
NP-MRD IDNP0301986
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one
Description(3R,3aS,8aR)-8a-methyl-5-methylidene-3-(propan-2-yl)-decahydroazulen-4-one belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. (3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one is found in Leminda millecra. Based on a literature review very few articles have been published on (3R,3aS,8aR)-8a-methyl-5-methylidene-3-(propan-2-yl)-decahydroazulen-4-one.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0301986 ((3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one)


  Mrv1652309102217152D          

 16 17  0  0  1  0            999 V2000
    4.6713    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5603   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6680    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8611    2.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2201    3.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.4430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3526    1.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    2.7617    0.0000 O   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  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  6  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
Download

3D MOL for NP0301986 ((3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one)

Download
3D SDF for NP0301986 ((3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one)

  Mrv1652309102217152D          

 16 17  0  0  1  0            999 V2000
    4.6713    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5603   -0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6680    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8611    2.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2201    3.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.4430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3526    1.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    2.7617    0.0000 O   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  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  6  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0301986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@@]2(C)CCCC(=C)C(=O)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-10(2)12-7-9-15(4)8-5-6-11(3)14(16)13(12)15/h10,12-13H,3,5-9H2,1-2,4H3/t12-,13-,15-/m1/s1

> <INCHI_KEY>
XWNLLHLOYWVRDK-UMVBOHGHSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.476210227798937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,8aR)-8a-methyl-5-methylidene-3-(propan-2-yl)-decahydroazulen-4-one

> <JCHEM_LOGP>
4.513572693666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.908524190859844

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
67.32149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,8aR)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1H-azulen-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0301986 ((3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one)
Download
PDB for NP0301986 ((3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.720   4.515   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.760   3.311   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.428   1.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.760   0.536   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   0.193   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.054   1.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.779  -0.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   0.678   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.684   1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.114   4.634   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.607   4.954   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.144   5.779   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.054   2.694   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   3.654   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.916   5.155   0.000  0.00  0.00           O+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   14                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10    6   15                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0301986 ((3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one)
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SMILES for NP0301986 ((3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one)
CC(C)[C@H]1CC[C@@]2(C)CCCC(=C)C(=O)[C@@H]12
Download
INCHI for NP0301986 ((3r,3as,8ar)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1h-azulen-4-one)
InChI=1S/C15H24O/c1-10(2)12-7-9-15(4)8-5-6-11(3)14(16)13(12)15/h10,12-13H,3,5-9H2,1-2,4H3/t12-,13-,15-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H24O
Average Mass220.3560 Da
Monoisotopic Mass220.18272 Da
IUPAC Name(3R,3aS,8aR)-8a-methyl-5-methylidene-3-(propan-2-yl)-decahydroazulen-4-one
Traditional Name(3R,3aS,8aR)-3-isopropyl-8a-methyl-5-methylidene-hexahydro-1H-azulen-4-one
CAS Registry NumberNot Available
SMILES
CC(C)[C@H]1CC[C@@]2(C)CCCC(=C)C(=O)[C@@H]12
InChI Identifier
InChI=1S/C15H24O/c1-10(2)12-7-9-15(4)8-5-6-11(3)14(16)13(12)15/h10,12-13H,3,5-9H2,1-2,4H3/t12-,13-,15-/m1/s1
InChI KeyXWNLLHLOYWVRDK-UMVBOHGHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Leminda millecraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentGermacrane sesquiterpenoids  
Alternative Parents
Substituents
  • Germacrane sesquiterpenoid
    • 

  • 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
logP4.51ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.32 m³·mol⁻¹ChemAxon
Polarizability26.48 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 Compound163008720  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]