NP-MRD: Showing NP-Card for (1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate (NP0219474)

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Record Information

Version

1.0

Created at

2022-09-05 20:28:31 UTC

Updated at

2022-09-05 20:28:32 UTC

NP-MRD ID

NP0219474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate

Description

(1S,3S,7S,8R)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]Tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate 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. (1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate is found in Eremanthus erythropappus. Based on a literature review very few articles have been published on (1S,3S,7S,8R)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]Tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222282D          

 24 26  0  0  1  0            999 V2000
    3.5079    4.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813    3.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    2.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665    3.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783    3.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    2.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    1.6859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3126    2.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923    2.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1550    2.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8804    1.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107    0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0480   -0.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4361   -0.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633   -0.5159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5836   -0.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.1256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9109   -0.2853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227    0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3301    0.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855    1.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5964    1.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652    0.9330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5683    0.5801    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 21  1  1  0  0  0
 17 23  1  0  0  0  0
  7 23  1  0  0  0  0
 15 24  1  6  0  0  0
 11 24  1  0  0  0  0
M  END


  Mrv1652309052222282D          

 24 26  0  0  1  0            999 V2000
    3.5079    4.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813    3.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    2.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665    3.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783    3.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    2.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    1.6859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3126    2.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923    2.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1550    2.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8804    1.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107    0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0480   -0.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4361   -0.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633   -0.5159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5836   -0.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.1256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9109   -0.2853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227    0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3301    0.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855    1.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5964    1.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652    0.9330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5683    0.5801    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 21  1  1  0  0  0
 17 23  1  0  0  0  0
  7 23  1  0  0  0  0
 15 24  1  6  0  0  0
 11 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C(=O)O[C@@H]1\C=C(C)/C2=CC(=O)[C@H](C[C@@H]3OC(=O)C(=C)[C@H]13)O2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-8(2)17(20)23-14-5-9(3)12-6-11(19)13(22-12)7-15-16(14)10(4)18(21)24-15/h5-6,13-16H,1,4,7H2,2-3H3/b9-5-/t13-,14+,15-,16+/m0/s1

> <INCHI_KEY>
MFOWZFZXFMFYTH-RYQCEGGUSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.336

> <EXACT_MASS>
330.1103383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.01030277997438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,7S,8R,9Z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate

> <JCHEM_LOGP>
2.251170868333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.470687885017792

> <JCHEM_PKA_STRONGEST_BASIC>
-4.865295174192071

> <JCHEM_POLAR_SURFACE_AREA>
78.90000000000002

> <JCHEM_REFRACTIVITY>
85.8403

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,7S,8R,9Z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.548   7.664   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.872   6.158   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.730   5.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.337   5.686   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.480   6.719   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.661   4.180   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.519   3.147   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.183   3.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.652   3.750   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.023   5.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.510   2.717   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.193   1.210   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.823  -0.196   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.681  -1.229   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.158  -0.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.689  -0.799   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.832   0.234   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.167  -0.533   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.309   0.501   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.816   0.184   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.680   1.906   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.447   3.241   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.148   1.742   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.794   1.083   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17    7                                                  
CONECT   24   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(1S,3S,7S,8R)-10-Methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0,]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoic acid	Generator

Chemical Formula

C₁₈H₁₈O₆

Average Mass

330.3360 Da

Monoisotopic Mass

330.11034 Da

IUPAC Name

(1S,3S,7S,8R,9Z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate

Traditional Name

(1S,3S,7S,8R,9Z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0^{3,7}]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=C)C(=O)O[C@@H]1\C=C(C)/C2=CC(=O)[C@H](C[C@@H]3OC(=O)C(=C)[C@H]13)O2

InChI Identifier

InChI=1S/C18H18O6/c1-8(2)17(20)23-14-5-9(3)12-6-11(19)13(22-12)7-15-16(14)10(4)18(21)24-15/h5-6,13-16H,1,4,7H2,2-3H3/b9-5-/t13-,14+,15-,16+/m0/s1

InChI Key

MFOWZFZXFMFYTH-RYQCEGGUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eremanthus erythropappus	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
Sesquiterpenoid
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Dihydrofuran
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	2.25	ChemAxon
pKa (Strongest Acidic)	8.47	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.84 m³·mol⁻¹	ChemAxon
Polarizability	32.01 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

163024449

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate (NP0219474)

MOL for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)

3D MOL for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)

3D SDF for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)

3D-SDF for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)

PDB for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)

3D PDB for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)

SMILES for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)

INCHI for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)

Structure for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)

3D Structure for NP0219474 ((1s,3s,7s,8r,9z)-10-methyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradeca-9,11-dien-8-yl 2-methylprop-2-enoate)