NP-MRD: Showing NP-Card for (1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one (NP0255660)

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Record Information

Version

2.0

Created at

2022-09-07 20:13:38 UTC

Updated at

2022-09-07 20:13:38 UTC

NP-MRD ID

NP0255660

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one

Description

(1R,3S,5R,7R,11R)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]Tetradec-8-en-13-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on (1R,3S,5R,7R,11R)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]Tetradec-8-en-13-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072222132D          

 19 21  0  0  1  0            999 V2000
    3.6734    0.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1931    0.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3681    0.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186    1.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894    2.2247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8813    3.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6373    3.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292    4.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3013    2.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0573    3.2157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1492    4.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214    2.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295    1.9063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4493    1.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5376    1.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8735    1.5760    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2094    2.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534    1.7352    0.0000 C   0  0  2  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  4  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 17 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19  2  1  6  0  0  0
  6 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255660

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@]2(C)O[C@H]2C[C@H]2[C@@H](CC(C)=C1)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O3/c1-9-5-10(2)8-16(4)14(19-16)7-12-11(3)15(17)18-13(12)6-9/h5,10,12-14H,3,6-8H2,1-2,4H3/t10-,12+,13+,14-,16+/m0/s1

> <INCHI_KEY>
ALZAUQVBTYKTMB-OIUQYKKBSA-N

> <FORMULA>
C16H22O3

> <MOLECULAR_WEIGHT>
262.349

> <EXACT_MASS>
262.156894568

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.820381837572036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,5R,7R,11R)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0^{3,5}]tetradec-8-en-13-one

> <JCHEM_LOGP>
3.0464967746666662

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.223697489314034

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
73.40950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5R,7R,11R)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0^{3,5}]tetradec-8-en-13-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.857   0.526   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.960   1.778   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.420   1.788   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.507   0.549   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.955   3.256   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.207   4.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.378   5.683   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.790   6.300   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.961   7.830   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.029   5.386   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.440   6.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.612   7.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.680   5.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.508   3.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.039   3.387   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.337   2.028   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.097   2.942   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.858   3.856   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.446   3.239   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   14   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂O₃

Average Mass

262.3490 Da

Monoisotopic Mass

262.15689 Da

IUPAC Name

(1R,3S,5R,7R,11R)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0^{3,5}]tetradec-8-en-13-one

Traditional Name

(1R,3S,5R,7R,11R)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0^{3,5}]tetradec-8-en-13-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@]2(C)O[C@H]2C[C@H]2[C@@H](CC(C)=C1)OC(=O)C2=C

InChI Identifier

InChI=1S/C16H22O3/c1-9-5-10(2)8-16(4)14(19-16)7-12-11(3)15(17)18-13(12)6-9/h5,10,12-14H,3,6-8H2,1-2,4H3/t10-,12+,13+,14-,16+/m0/s1

InChI Key

ALZAUQVBTYKTMB-OIUQYKKBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Germacrane sesquiterpenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.05	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.41 m³·mol⁻¹	ChemAxon
Polarizability	28.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163006057

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one (NP0255660)

MOL for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)

3D MOL for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)

3D SDF for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)

3D-SDF for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)

PDB for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)

3D PDB for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)

SMILES for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)

INCHI for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)

Structure for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)

3D Structure for NP0255660 ((1r,3s,5r,7r,11r)-5,7,9-trimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-13-one)