NP-MRD: Showing NP-Card for {3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate (NP0227256)

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Record Information

Version

2.0

Created at

2022-09-06 06:31:21 UTC

Updated at

2022-09-06 06:31:21 UTC

NP-MRD ID

NP0227256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate

Description

{3-Methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]Tetradec-8-en-8-yl}methyl acetate belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. {3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate is found in Mikania cordata and Mikania trachypleura. {3-Methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]Tetradec-8-en-8-yl}methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171507192D          

 22 24  0  0  0  0            999 V2000
    1.9695    4.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255    4.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3895    5.0595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8174    3.7502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5733    3.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6652    2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3293    3.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853    2.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1772    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5131    1.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7571    1.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931    1.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    0.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4290    0.8010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371    1.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    2.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093    2.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7735    0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5985    0.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880    0.0085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8480    1.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6308    1.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  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  1  0  0  0  0
 14 15  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0227256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=CCC2C(CC3(C)OC3CC1)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-10-13-6-4-12(9-20-11(2)18)5-7-15-17(3,22-15)8-14(13)21-16(10)19/h4,13-15H,1,5-9H2,2-3H3

> <INCHI_KEY>
PCJJNZDKLXQNIP-UHFFFAOYSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.61780034730114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
1.8470379259999998

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2234397462128

> <JCHEM_POLAR_SURFACE_AREA>
65.13

> <JCHEM_REFRACTIVITY>
79.7435

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       3.676   9.147   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.088   8.531   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.327   9.444   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.259   7.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.670   6.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.842   4.853   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.081   5.767   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.493   5.150   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.664   3.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.424   2.706   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.013   3.323   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.774   2.409   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.688   1.169   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.534   1.495   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.363   3.026   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.191   4.556   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.431   5.470   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.910   1.245   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.450   1.256   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.364   0.016   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.916   2.723   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.378   3.209   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   12   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    6                                                       
CONECT   18   10   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    9   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
{3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0,]tetradec-8-en-8-yl}methyl acetic acid	Generator
{3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

{3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate

Traditional Name

{3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=CCC2C(CC3(C)OC3CC1)OC(=O)C2=C

InChI Identifier

InChI=1S/C17H22O5/c1-10-13-6-4-12(9-20-11(2)18)5-7-15-17(3,22-15)8-14(13)21-16(10)19/h4,13-15H,1,5-9H2,2-3H3

InChI Key

PCJJNZDKLXQNIP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mikania cordata	LOTUS Database	35616633
Mikania trachypleura	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	2.49	ALOGPS
logP	1.85	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.74 m³·mol⁻¹	ChemAxon
Polarizability	31.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate (NP0227256)

MOL for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)

3D MOL for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)

3D SDF for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)

3D-SDF for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)

PDB for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)

3D PDB for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)

SMILES for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)

INCHI for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)

Structure for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)

3D Structure for NP0227256 ({3-methyl-12-methylidene-13-oxo-4,14-dioxatricyclo[9.3.0.0³,⁵]tetradec-8-en-8-yl}methyl acetate)