NP-MRD: Showing NP-Card for 4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene (NP0181059)

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Record Information

Version

2.0

Created at

2022-09-03 19:30:43 UTC

Updated at

2022-09-03 19:30:43 UTC

NP-MRD ID

NP0181059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene

Description

1,7,11-Trimethyl-4-(propan-2-yl)cyclotetradeca-1,3,7,11-tetraene belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions. 4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene is found in Armina maculata, Klyxum flaccidum, Sarcophyton ehrenbergi and Sarcophyton trocheliophorum. 1,7,11-Trimethyl-4-(propan-2-yl)cyclotetradeca-1,3,7,11-tetraene is possibly neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 52  0  0  0  0  0  0  0  0999 V2000
    0.7022    3.6487   -1.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710    2.8080   -0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3664    2.5892   -1.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626    1.8369   -0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3250    0.5130   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3685   -0.0772    0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8735   -0.4593    2.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2456   -1.0812    0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963   -0.4167   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978   -1.6144    0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -2.5378   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6175   -3.5232   -1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1447   -2.4958   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7779   -1.5644    0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643   -1.0528    0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776    0.1315    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -0.0716    1.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0192    1.3615    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0274    1.7311   -0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503    2.2921    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2326    3.0353   -2.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    4.3794   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293    4.2871   -2.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859    3.1020   -2.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0402    2.4056    0.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857    0.7914    0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7067   -1.5166    2.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199   -0.1542    2.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975    0.2050    2.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3038   -0.7662   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058   -1.3472   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -1.9810    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458    0.0349   -1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8615   -0.7250   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.2621    1.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -2.2429    0.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8616   -4.4578   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5767   -3.2302   -2.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1493   -3.8325   -2.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -3.1844   -0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -2.1157    1.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1839   -0.7025    0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8384   -1.8376    0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8904   -0.8256   -1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4759    0.3185    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5533   -1.1321    2.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855    0.5033    2.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3819    2.1688    1.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777    0.9187   -1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4396    2.5573   -1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2478    1.4814    0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9717    3.1074    0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 20  1  0
 20 19  1  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  1  0
  9  5  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  6 26  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  4 25  1  0
  3 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 20 51  1  0
 20 52  1  0
 19 49  1  0
 19 50  1  0
 18 48  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 15 43  1  0
 15 44  1  0
 14 41  1  0
 14 42  1  0
 13 40  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 10 35  1  0
 10 36  1  0
  9 33  1  0
  9 34  1  0
M  END


  Mrv1533004181501292D          

 20 20  0  0  0  0            999 V2000
    0.7060    1.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    1.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562    2.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    1.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4064    0.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -0.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364   -0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963   -1.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -2.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461   -1.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360   -1.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161   -0.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760    1.0410    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0181059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC=C(C)CCC=C(C)CCC=C(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-16(2)20-14-12-18(4)10-6-8-17(3)9-7-11-19(5)13-15-20/h8,11-12,14,16H,6-7,9-10,13,15H2,1-5H3

> <INCHI_KEY>
UJUWZMUCEGGBOH-UHFFFAOYSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.18661861038648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,7,11-trimethyl-4-(propan-2-yl)cyclotetradeca-1,3,7,11-tetraene

> <ALOGPS_LOGP>
7.15

> <JCHEM_LOGP>
6.481307531333332

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
95.158

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       1.318   3.398   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.830   3.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.838   4.272   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.334   1.652   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.342   2.816   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.855   2.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.359   1.070   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.871   0.779   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.351  -0.094   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.855  -1.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.846  -2.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.334  -2.422   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.838  -3.877   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.326  -3.586   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.814  -3.295   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.310  -1.840   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.318  -0.676   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.830  -0.967   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.814   0.779   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.822   1.943   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    4                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂

Average Mass

272.4760 Da

Monoisotopic Mass

272.25040 Da

IUPAC Name

1,7,11-trimethyl-4-(propan-2-yl)cyclotetradeca-1,3,7,11-tetraene

Traditional Name

4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC=C(C)CCC=C(C)CCC=C(C)CC1

InChI Identifier

InChI=1S/C20H32/c1-16(2)20-14-12-18(4)10-6-8-17(3)9-7-11-19(5)13-15-20/h8,11-12,14,16H,6-7,9-10,13,15H2,1-5H3

InChI Key

UJUWZMUCEGGBOH-UHFFFAOYSA-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
Armina maculata	LOTUS Database	35616633
Klyxum flaccidum	LOTUS Database	35616633
Sarcophyton ehrenbergi	LOTUS Database	35616633
Sarcophyton trocheliophorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cembrane diterpenoids. These are diterpenoids with a structure based a cembrane skeleton, which is characterized by the presence of an isopropyl group at C-1 and by three symmetrically disposed methyl groups a the t C-4, -8 and -12 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Cembrane diterpenoids

Alternative Parents

Substituents

Cembrane diterpenoid
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	7.15	ALOGPS
logP	6.48	ChemAxon
logS	-4.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.16 m³·mol⁻¹	ChemAxon
Polarizability	35.19 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

4076633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene (NP0181059)

MOL for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)

3D MOL for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)

3D SDF for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)

3D-SDF for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)

PDB for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)

3D PDB for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)

SMILES for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)

INCHI for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)

Structure for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)

3D Structure for NP0181059 (4-isopropyl-1,7,11-trimethylcyclotetradeca-1,3,7,11-tetraene)