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Showing NP-Card for ent-15b,16b-Epoxy-3-kauranone (NP0335739)

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Record Information
Version2.0
Created at2024-09-11 03:00:16 UTC
Updated at2024-09-11 03:00:16 UTC
NP-MRD IDNP0335739
Secondary Accession NumbersNone
Natural Product Identification
Common Nameent-15b,16b-Epoxy-3-kauranone
DescriptionEnt-15b,16b-Epoxy-3-kauranone belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Based on a literature review very few articles have been published on ent-15b,16b-Epoxy-3-kauranone.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335739 (ent-15b,16b-Epoxy-3-kauranone)


  Mrv2104 05262305322D          

 22 26  0  0  0  0            999 V2000
    4.1140    3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1565    3.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4372    1.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425    1.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9409    0.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355    0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1166    3.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9930    1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2148    1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282    2.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    0.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407    2.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008    1.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1450    2.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306    2.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188    2.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886    1.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7593    1.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    2.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9232    2.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4086    2.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 17  1  1  0  0  0  0
 17  2  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18  3  1  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19  4  1  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20 10  1  0  0  0  0
 20 11  1  0  0  0  0
 20 14  1  0  0  0  0
 20 16  1  0  0  0  0
 21 15  2  0  0  0  0
 22 16  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
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3D MOL for NP0335739 (ent-15b,16b-Epoxy-3-kauranone)

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3D SDF for NP0335739 (ent-15b,16b-Epoxy-3-kauranone)

  Mrv2104 05262305322D          

 22 26  0  0  0  0            999 V2000
    4.1140    3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1565    3.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4372    1.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425    1.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9409    0.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355    0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1166    3.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9930    1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2148    1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282    2.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    0.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407    2.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8008    1.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1450    2.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306    2.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188    2.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886    1.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7593    1.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    2.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9232    2.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4086    2.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 17  1  1  0  0  0  0
 17  2  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18  3  1  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19  4  1  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20 10  1  0  0  0  0
 20 11  1  0  0  0  0
 20 14  1  0  0  0  0
 20 16  1  0  0  0  0
 21 15  2  0  0  0  0
 22 16  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12OC1C13CC2CCC1C1(C)CCC(=O)C(C)(C)C1CC3

> <INCHI_IDENTIFIER>
InChI=1/C20H30O2/c1-17(2)13-7-10-20-11-12(19(4)16(20)22-19)5-6-14(20)18(13,3)9-8-15(17)21/h12-14,16H,5-11H2,1-4H3

> <INCHI_KEY>
SVKMTDSTFGJBCS-UHFFFAOYNA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.16396122520008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,5,9,14-tetramethyl-15-oxapentacyclo[11.3.1.0^{1,10}.0^{4,9}.0^{14,16}]heptadecan-6-one

> <JCHEM_LOGP>
4.2240008153333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.230309350977824

> <JCHEM_POLAR_SURFACE_AREA>
29.6

> <JCHEM_REFRACTIVITY>
85.94159999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5,5,9,14-tetramethyl-15-oxapentacyclo[11.3.1.0^{1,10}.0^{4,9}.0^{14,16}]heptadecan-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0335739 (ent-15b,16b-Epoxy-3-kauranone)
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PDB for NP0335739 (ent-15b,16b-Epoxy-3-kauranone)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       7.680   6.826   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.625   6.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.416   1.946   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.079   2.322   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.623   0.732   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.106   1.322   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.818   5.992   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.320   2.968   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.868   2.457   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.346   5.484   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.204   2.805   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.342   1.723   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.983   4.973   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.228   2.939   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.604   4.481   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.297   4.348   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.435   5.484   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.699   3.459   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.417   3.084   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.927   3.948   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.057   4.992   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.763   4.478   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   19                                                            
CONECT    5    6   12                                                       
CONECT    6    5   14                                                       
CONECT    7   10   13                                                       
CONECT    8    9   15                                                       
CONECT    9    8   18                                                       
CONECT   10    7   20                                                       
CONECT   11   12   20                                                       
CONECT   12    5   11   19                                                  
CONECT   13    7   17   18                                                  
CONECT   14    6   18   20                                                  
CONECT   15    8   17   21                                                  
CONECT   16   19   20   22                                                  
CONECT   17    1    2   13   15                                             
CONECT   18    3    9   13   14                                             
CONECT   19    4   12   16   22                                             
CONECT   20   10   11   14   16                                             
CONECT   21   15                                                            
CONECT   22   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

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3D PDB for NP0335739 (ent-15b,16b-Epoxy-3-kauranone)
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SMILES for NP0335739 (ent-15b,16b-Epoxy-3-kauranone)
CC12OC1C13CC2CCC1C1(C)CCC(=O)C(C)(C)C1CC3
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INCHI for NP0335739 (ent-15b,16b-Epoxy-3-kauranone)
InChI=1/C20H30O2/c1-17(2)13-7-10-20-11-12(19(4)16(20)22-19)5-6-14(20)18(13,3)9-8-15(17)21/h12-14,16H,5-11H2,1-4H3
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SynonymsNot Available
Chemical FormulaC20H30O2
Average Mass302.4580 Da
Monoisotopic Mass302.22458 Da
IUPAC Name5,5,9,14-tetramethyl-15-oxapentacyclo[11.3.1.0^{1,10}.0^{4,9}.0^{14,16}]heptadecan-6-one
Traditional Name5,5,9,14-tetramethyl-15-oxapentacyclo[11.3.1.0^{1,10}.0^{4,9}.0^{14,16}]heptadecan-6-one
CAS Registry NumberNot Available
SMILES
CC12OC1C13CC2CCC1C1(C)CCC(=O)C(C)(C)C1CC3
InChI Identifier
InChI=1/C20H30O2/c1-17(2)13-7-10-20-11-12(19(4)16(20)22-19)5-6-14(20)18(13,3)9-8-15(17)21/h12-14,16H,5-11H2,1-4H3
InChI KeySVKMTDSTFGJBCS-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentKaurane diterpenoids  
Alternative Parents
Substituents
  • Kaurane diterpenoid
    • 

  • Oxane
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP4.22ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.94 m³·mol⁻¹ChemAxon
Polarizability35.16 ųChemAxon
Number of Rings5ChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available