NP-MRD: Showing NP-Card for (1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate (NP0221808)

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Record Information

Version

2.0

Created at

2022-09-05 23:28:25 UTC

Updated at

2022-09-05 23:28:25 UTC

NP-MRD ID

NP0221808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate

Description

(1R,2S,4E,8E,10R)-4,8,11,11-tetramethylbicyclo[8.1.0]Undeca-4,8-dien-2-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as bicyclogermacrane and isolepidozane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the bicyclogermacrane (3,7,11,11-tetramethylbicyclo[8.1.0]Undecane, 9CI) skeleton or the isolepidozane skeleton. (1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate is found in Senecio crassissimus and Stylotrichium rotundifolium. Based on a literature review very few articles have been published on (1R,2S,4E,8E,10R)-4,8,11,11-tetramethylbicyclo[8.1.0]Undeca-4,8-dien-2-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201282D          

 22 23  0  0  1  0            999 V2000
    4.1858    5.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5382    4.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0684    3.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4208    3.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2462    3.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8938    4.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7763    3.1363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1287    2.3903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9509    2.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3033    1.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5246    1.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1255    1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4779    0.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    0.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858    0.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7160   -0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335    0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0113    0.9662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6589    1.7122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1890    1.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    1.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801    0.3175    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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  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  2  0  0  0  0
 18 17  1  1  0  0  0
 19 18  1  0  0  0  0
 19  8  1  0  0  0  0
 19 20  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221808

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1C\C(C)=C\CC\C(C)=C\[C@@H]2[C@@H]1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-7-15(4)19(21)22-17-12-14(3)10-8-9-13(2)11-16-18(17)20(16,5)6/h7,10-11,16-18H,8-9,12H2,1-6H3/b13-11+,14-10+,15-7-/t16-,17+,18+/m1/s1

> <INCHI_KEY>
MLQMIURMODQIOF-GSXOEQPUSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.578403180463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4E,8E,10R)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
5.365548159000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.851306991955144

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
93.94720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4E,8E,10R)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

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       7.814   9.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.471   8.260   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.594   6.994   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.252   5.601   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.060   7.120   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.402   8.513   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.182   5.854   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.840   4.462   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.375   4.335   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.033   2.943   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.579   2.434   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.568   2.816   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.225   1.424   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.348   0.158   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.814   0.285   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.937  -0.981   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.156   1.677   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.621   1.804   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.963   3.196   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.086   1.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.568   2.190   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.323   0.593   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18    8   20                                                  
CONECT   20   19   18   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,4E,8E,10R)-4,8,11,11-Tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1C\C(C)=C\CC\C(C)=C\[C@@H]2[C@@H]1C2(C)C

InChI Identifier

InChI=1S/C20H30O2/c1-7-15(4)19(21)22-17-12-14(3)10-8-9-13(2)11-16-18(17)20(16,5)6/h7,10-11,16-18H,8-9,12H2,1-6H3/b13-11+,14-10+,15-7-/t16-,17+,18+/m1/s1

InChI Key

MLQMIURMODQIOF-GSXOEQPUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Senecio crassissimus	LOTUS Database	35616633
Stylotrichium rotundifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclogermacrane and isolepidozane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the bicyclogermacrane (3,7,11,11-tetramethylbicyclo[8.1.0]Undecane, 9CI) skeleton or the isolepidozane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Bicyclogermacrane and isolepidozane sesquiterpenoids

Alternative Parents

Substituents

Bicyclogermacrane sesquiterpenoid
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

163194085

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate (NP0221808)

MOL for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)

PDB for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)

Structure for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0221808 ((1r,2s,4e,8e,10r)-4,8,11,11-tetramethylbicyclo[8.1.0]undeca-4,8-dien-2-yl (2z)-2-methylbut-2-enoate)