NP-MRD: Showing NP-Card for (2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate (NP0226148)

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Record Information

Version

2.0

Created at

2022-09-06 05:06:06 UTC

Updated at

2022-09-06 05:06:06 UTC

NP-MRD ID

NP0226148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate

Description

(2Z,4R,8R,9R,11S)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]Tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate is found in Dendroviguiera eriophora. Based on a literature review very few articles have been published on (2Z,4R,8R,9R,11S)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]Tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207062D          

 26 28  0  0  1  0            999 V2000
    0.5371   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6204    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8900   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    3.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9060    4.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4337    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    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
  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  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  1  0  0  0
 20 26  1  0  0  0  0
  7 26  1  0  0  0  0
M  END


  Mrv1652309062207062D          

 26 28  0  0  1  0            999 V2000
    0.5371   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6204    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8900   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    3.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9060    4.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4337    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    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
  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  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  1  0  0  0
 20 26  1  0  0  0  0
  7 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C(=O)O[C@@H]1C[C@]2(C)OC(=CC2=O)\C(CO)=C/[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O7/c1-9(2)17(22)25-14-7-19(4)15(21)6-12(26-19)11(8-20)5-13-16(14)10(3)18(23)24-13/h5-6,13-14,16,20H,1,3,7-8H2,2,4H3/b11-5-/t13-,14-,16+,19+/m1/s1

> <INCHI_KEY>
HTMCLLSRQWRPTN-IDRGXCFGSA-N

> <FORMULA>
C19H20O7

> <MOLECULAR_WEIGHT>
360.362

> <EXACT_MASS>
360.120902984

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.32606233557081

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4R,8R,9R,11S)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate

> <JCHEM_LOGP>
1.4031655976666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.021146287600608

> <JCHEM_PKA_STRONGEST_BASIC>
-2.789550613803476

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
92.32830000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4R,8R,9R,11S)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate

> <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       1.003  -4.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.376  -3.129   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.155  -2.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.281  -1.883   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.813  -2.044   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.655  -0.476   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.560   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.025   0.294   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.489   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.395  -0.476   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.985   2.786   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.489   4.802   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.395   3.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.395   2.016   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.859   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.025   5.278   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.025   6.818   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.691   7.588   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.560   4.802   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.655   3.556   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.810   4.032   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.715   2.786   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.255   2.786   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.810   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.286   0.075   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+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   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   14                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20    7                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(2Z,4R,8R,9R,11S)-2-(Hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0,]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoic acid	Generator

Chemical Formula

C₁₉H₂₀O₇

Average Mass

360.3620 Da

Monoisotopic Mass

360.12090 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=C)C(=O)O[C@@H]1C[C@]2(C)OC(=CC2=O)\C(CO)=C/[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H20O7/c1-9(2)17(22)25-14-7-19(4)15(21)6-12(26-19)11(8-20)5-13-16(14)10(3)18(23)24-13/h5-6,13-14,16,20H,1,3,7-8H2,2,4H3/b11-5-/t13-,14-,16+,19+/m1/s1

InChI Key

HTMCLLSRQWRPTN-IDRGXCFGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Viguiera eriophora	LOTUS Database	35616633

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
Gamma butyrolactone
3-furanone
Dicarboxylic acid or derivatives
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Dihydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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

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

162911613

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate (NP0226148)

MOL for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D MOL for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D SDF for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D-SDF for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

PDB for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D PDB for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

SMILES for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

INCHI for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

Structure for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D Structure for NP0226148 ((2z,4r,8r,9r,11s)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)