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Showing NP-Card for 12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione (NP0322903)

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Record Information
Version2.0
Created at2022-09-12 01:58:30 UTC
Updated at2022-09-12 01:58:31 UTC
NP-MRD IDNP0322903
Secondary Accession NumbersNone
Natural Product Identification
Common Name12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione
Description13-Methoxy-2,6,6-trimethyl-12-(propan-2-yl)-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]Pentadec-12-ene-9,11,14-trione belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione is found in Taiwania cryptomerioides. 13-Methoxy-2,6,6-trimethyl-12-(propan-2-yl)-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]Pentadec-12-ene-9,11,14-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0322903 (12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione)


  Mrv1533004261505242D          

 26 29  0  0  0  0            999 V2000
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   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
    1.9520    1.1270    0.0000 O   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
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772    1.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587    1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  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
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
Download

3D MOL for NP0322903 (12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione)

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3D SDF for NP0322903 (12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione)

  Mrv1533004261505242D          

 26 29  0  0  0  0            999 V2000
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   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
    1.9520    1.1270    0.0000 O   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
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772    1.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587    1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  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
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0322903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C(C)C)C(=O)C23OC2(C1=O)C1(C)CCCC(C)(C)C1CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-11(2)14-15(25-6)17(24)21-19(5)9-7-8-18(3,4)12(19)10-13(22)20(21,26-21)16(14)23/h11-12H,7-10H2,1-6H3

> <INCHI_KEY>
FYLUPAHQDHDVMV-UHFFFAOYSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.45

> <EXACT_MASS>
360.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.03057444287168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-methoxy-2,6,6-trimethyl-12-(propan-2-yl)-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
4.097184959333332

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.387762045594418

> <JCHEM_PKA_STRONGEST_BASIC>
-4.314527564160576

> <JCHEM_POLAR_SURFACE_AREA>
72.97

> <JCHEM_REFRACTIVITY>
96.40379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0322903 (12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione)
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PDB for NP0322903 (12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione)
HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.644   2.104   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.171   2.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.456   3.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   25                                             
CONECT   11   10   12                                                       
CONECT   12   11   10   13   15                                             
CONECT   13   12    3   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   15   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   10   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

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3D PDB for NP0322903 (12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione)
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SMILES for NP0322903 (12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione)
COC1=C(C(C)C)C(=O)C23OC2(C1=O)C1(C)CCCC(C)(C)C1CC3=O
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INCHI for NP0322903 (12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione)
InChI=1S/C21H28O5/c1-11(2)14-15(25-6)17(24)21-19(5)9-7-8-18(3,4)12(19)10-13(22)20(21,26-21)16(14)23/h11-12H,7-10H2,1-6H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC21H28O5
Average Mass360.4500 Da
Monoisotopic Mass360.19367 Da
IUPAC Name13-methoxy-2,6,6-trimethyl-12-(propan-2-yl)-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione
Traditional Name12-isopropyl-13-methoxy-2,6,6-trimethyl-15-oxatetracyclo[8.4.1.0¹,¹⁰.0²,⁷]pentadec-12-ene-9,11,14-trione
CAS Registry NumberNot Available
SMILES
COC1=C(C(C)C)C(=O)C23OC2(C1=O)C1(C)CCCC(C)(C)C1CC3=O
InChI Identifier
InChI=1S/C21H28O5/c1-11(2)14-15(25-6)17(24)21-19(5)9-7-8-18(3,4)12(19)10-13(22)20(21,26-21)16(14)23/h11-12H,7-10H2,1-6H3
InChI KeyFYLUPAHQDHDVMV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Taiwania cryptomerioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentDiterpenoids  
Alternative Parents
Substituents
  • Abietane diterpenoid
    • 

  • Diterpenoid
    • 

  • Cyclohexenone
    • 

  • Oxepane
    • 

  • Vinylogous ester
    • 

  • Ketone
    • 

  • Dialkyl ether
    • 

  • Oxirane
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP3.37ALOGPS
logP4.1ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)17.39ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area72.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.4 m³·mol⁻¹ChemAxon
Polarizability39.03 ųChemAxon
Number of Rings4ChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]