NP-MRD: Showing NP-Card for (1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one (NP0225772)

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Record Information

Version

2.0

Created at

2022-09-06 04:35:51 UTC

Updated at

2022-09-06 04:35:51 UTC

NP-MRD ID

NP0225772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one

Description

(1R,2Z,4R,8R,9R,11R)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]Tetradeca-2,12-dien-6-one belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. (1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one is found in Greenmaniella resinosa. Based on a literature review very few articles have been published on (1R,2Z,4R,8R,9R,11R)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]Tetradeca-2,12-dien-6-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206352D          

 25 27  0  0  1  0            999 V2000
    5.4278   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9034    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    1.4924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8492    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0287    2.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8492   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3883   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6041    0.4125    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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24  2  1  6  0  0  0
  6 24  1  0  0  0  0
 15 25  1  0  0  0  0
 10 25  1  0  0  0  0
M  END


  Mrv1652309062206352D          

 25 27  0  0  1  0            999 V2000
    5.4278   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9034    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    1.4924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8492    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0287    2.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8492   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3883   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6041    0.4125    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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24  2  1  6  0  0  0
  6 24  1  0  0  0  0
 15 25  1  0  0  0  0
 10 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225772

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]12O[C@](C)(C[C@@H](OCC(C)C)[C@@H]3[C@H](OC(=O)C3=C)\C=C1\C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-12(2)11-23-16-10-19(5)7-8-20(22-6,25-19)13(3)9-15-17(16)14(4)18(21)24-15/h7-9,12,15-17H,4,10-11H2,1-3,5-6H3/b13-9-/t15-,16-,17+,19+,20-/m1/s1

> <INCHI_KEY>
OCMNFBXJZYUCJE-KMPYGETESA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.439

> <EXACT_MASS>
348.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.55724691672835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2Z,4R,8R,9R,11R)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-6-one

> <JCHEM_LOGP>
3.632287277333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.826024782279394

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
95.9105

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2Z,4R,8R,9R,11R)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      10.132  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.656  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.561   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.101   0.770   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.656   2.016   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.191   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.286   2.786   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.822   3.262   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.822   4.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.357   2.786   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.452   4.032   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.920   3.871   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.452   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.452  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.357  -1.246   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.452  -2.492   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.822  -1.722   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.286  -1.246   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.191  -2.492   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.565  -3.899   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.034  -4.060   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.407  -5.466   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.128  -2.814   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.191  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.861   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13   25                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   25                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18    2    6                                                  
CONECT   25   15   10                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₅

Average Mass

348.4390 Da

Monoisotopic Mass

348.19367 Da

IUPAC Name

(1R,2Z,4R,8R,9R,11R)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-6-one

Traditional Name

(1R,2Z,4R,8R,9R,11R)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-6-one

CAS Registry Number

Not Available

SMILES

CO[C@]12O[C@](C)(C[C@@H](OCC(C)C)[C@@H]3[C@H](OC(=O)C3=C)\C=C1\C)C=C2

InChI Identifier

InChI=1S/C20H28O5/c1-12(2)11-23-16-10-19(5)7-8-20(22-6,25-19)13(3)9-15-17(16)14(4)18(21)24-15/h7-9,12,15-17H,4,10-11H2,1-3,5-6H3/b13-9-/t15-,16-,17+,19+,20-/m1/s1

InChI Key

OCMNFBXJZYUCJE-KMPYGETESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Greenmaniella resinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Gamma butyrolactone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
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	3.63	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.91 m³·mol⁻¹	ChemAxon
Polarizability	37.56 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

163025477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one (NP0225772)

MOL for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)

3D MOL for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)

3D SDF for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)

3D-SDF for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)

PDB for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)

3D PDB for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)

SMILES for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)

INCHI for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)

Structure for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)

3D Structure for NP0225772 ((1r,2z,4r,8r,9r,11r)-1-methoxy-2,11-dimethyl-7-methylidene-9-(2-methylpropoxy)-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-6-one)