NP-MRD: Showing NP-Card for 11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate (NP0318268)

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Record Information

Version

2.0

Created at

2022-09-11 18:39:53 UTC

Updated at

2022-09-11 18:39:53 UTC

NP-MRD ID

NP0318268

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate

Description

11-Hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]Tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. 11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate is found in Montanoa guatemalensis. 11-Hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]Tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231520442D          

 27 30  0  0  0  0            999 V2000
    1.1916   -0.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897    0.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7755    1.4785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005    1.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474    2.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4225    1.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942    2.0873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729    0.6635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950    0.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    1.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7162    2.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5382    1.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886    1.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4170    0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -0.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5143    0.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1178   -0.9702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2958   -0.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4737   -0.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8717   -1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492   -0.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023   -1.3464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047   -0.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407    0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233   -0.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994    0.4564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658    2.7642    0.0000 C   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  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  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  2  0  0  0  0
 12 13  1  4  0  0  0
 13 14  1  0  0  0  0
 14 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
 15 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
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  9 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 27  1  0  0  0  0
M  END


  Mrv1533004231520442D          

 27 30  0  0  0  0            999 V2000
    1.1916   -0.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897    0.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7755    1.4785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005    1.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474    2.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4225    1.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942    2.0873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729    0.6635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950    0.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    1.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7162    2.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5382    1.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886    1.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4170    0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -0.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5143    0.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1178   -0.9702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2958   -0.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4737   -0.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8717   -1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492   -0.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023   -1.3464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047   -0.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407    0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233   -0.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994    0.4564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658    2.7642    0.0000 C   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  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  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  2  0  0  0  0
 12 13  1  4  0  0  0
 13 14  1  0  0  0  0
 14 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
 15 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
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  9 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318268

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC1(C)C(=O)OC1CC(C)=CCCC2(C)OC2C2OC(=O)C(=C)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O7/c1-10-7-6-8-18(4)14(27-18)15-20(23,11(2)16(21)25-15)13(9-10)24-17(22)19(5)12(3)26-19/h7,12-15,23H,2,6,8-9H2,1,3-5H3

> <INCHI_KEY>
VIRIAKAYXFJSGP-UHFFFAOYSA-N

> <FORMULA>
C20H26O7

> <MOLECULAR_WEIGHT>
378.421

> <EXACT_MASS>
378.167853177

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.32295702727254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.227726539333334

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.967791641579844

> <JCHEM_PKA_STRONGEST_BASIC>
-3.968486171043844

> <JCHEM_POLAR_SURFACE_AREA>
97.89

> <JCHEM_REFRACTIVITY>
93.72479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       2.224  -0.112   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.221   1.428   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.448   2.760   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.988   2.763   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.635   4.161   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.522   2.633   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.402   3.896   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.176   1.239   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.711   1.108   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.057   2.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.937   3.766   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.471   3.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.125   2.241   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.245   0.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.899  -0.417   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.293   0.237   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.553  -1.811   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.019  -1.680   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.484  -1.550   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.360  -2.603   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.012  -1.859   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.618  -2.513   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.302  -0.347   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.249   0.777   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.830  -0.156   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.666   0.852   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.283   5.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    4                                                       
CONECT    4    3    2    5    6                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   15   19                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    9   19   26                                             
CONECT   26   25                                                            
CONECT   27   11                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
11-Hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0,]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylic acid	Generator
11-Hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₆O₇

Average Mass

378.4210 Da

Monoisotopic Mass

378.16785 Da

IUPAC Name

11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate

Traditional Name

11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC1OC1(C)C(=O)OC1CC(C)=CCCC2(C)OC2C2OC(=O)C(=C)C12O

InChI Identifier

InChI=1S/C20H26O7/c1-10-7-6-8-18(4)14(27-18)15-20(23,11(2)16(21)25-15)13(9-10)24-17(22)19(5)12(3)26-19/h7,12-15,23H,2,6,8-9H2,1,3-5H3

InChI Key

VIRIAKAYXFJSGP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Montanoa guatemalensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	1.82	ALOGPS
logP	2.23	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.97	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.72 m³·mol⁻¹	ChemAxon
Polarizability	38.32 Å³	ChemAxon
Number of Rings	4	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 11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate (NP0318268)

MOL for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)

3D MOL for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)

3D SDF for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)

3D-SDF for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)

PDB for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)

3D PDB for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)

SMILES for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)

INCHI for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)

Structure for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)

3D Structure for NP0318268 (11-hydroxy-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl 2,3-dimethyloxirane-2-carboxylate)