NP-MRD: Showing NP-Card for (1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate (NP0158049)

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Record Information

Version

2.0

Created at

2022-09-02 15:34:06 UTC

Updated at

2022-09-02 15:34:06 UTC

NP-MRD ID

NP0158049

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate

Description

(1S,4S,5S,6S,9S,10R,12R,14R)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-6-yl (3E)-hexa-3,5-dienoate belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. Based on a literature review very few articles have been published on (1S,4S,5S,6S,9S,10R,12R,14R)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-6-yl (3E)-hexa-3,5-dienoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217342D          

 32 35  0  0  1  0            999 V2000
   -2.0211    3.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2863    2.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941    3.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1407    2.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330    3.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678    2.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2600    3.2265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6103    1.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3451    1.5787    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0184    2.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866    2.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260    3.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8184    1.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1698    1.0288    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5466    0.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0477   -0.1113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2748   -0.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022217342D          

 32 35  0  0  1  0            999 V2000
   -2.0211    3.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2863    2.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0158049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2[C@H]([C@@H]3C=C(CO)[C@H](OC(=O)C\C=C\C=C)[C@@]4(O)[C@@H](O)C(C)=C[C@@]14C3=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O6/c1-6-7-8-9-19(28)32-23-16(13-27)11-17-20-18(24(20,4)5)10-15(3)25(22(17)30)12-14(2)21(29)26(23,25)31/h6-8,11-12,15,17-18,20-21,23,27,29,31H,1,9-10,13H2,2-5H3/b8-7+/t15-,17+,18-,20+,21+,23+,25+,26+/m1/s1

> <INCHI_KEY>
AWRJTPFCJAMATC-NGAHXIQYSA-N

> <FORMULA>
C26H34O6

> <MOLECULAR_WEIGHT>
442.552

> <EXACT_MASS>
442.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.59955574686689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5S,6S,9S,10R,12R,14R)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-6-yl (3E)-hexa-3,5-dienoate

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.1021256356666664

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.50974745045568

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.105993625596728

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7642725399807624

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
122.76899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5S,6S,9S,10R,12R,14R)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-6-yl (3E)-hexa-3,5-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.773   5.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.401   4.910   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.109   5.748   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.263   5.047   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.555   5.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.927   5.185   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.219   6.023   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.006   3.647   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.378   2.947   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.634   3.862   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.388   5.383   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.582   6.356   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.128   3.386   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.784   1.920   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.620   1.016   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.556  -0.208   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.485   0.162   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.467  -1.081   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.973  -0.670   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.765  -1.626   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.915   0.869   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.648   1.744   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.373   1.360   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.124   2.261   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.366  -1.255   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.449  -2.492   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.906  -1.666   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.116  -0.667   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.025   0.871   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.402   0.180   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.609   1.136   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.713  -0.627   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23   25                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    9   17   24                                             
CONECT   24   23                                                            
CONECT   25   17   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28   14   30                                                  
CONECT   30   29   28   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1S,4S,5S,6S,9S,10R,12R,14R)-4,5-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0,.0,]pentadeca-2,7-dien-6-yl (3E)-hexa-3,5-dienoic acid	Generator

Chemical Formula

C₂₆H₃₄O₆

Average Mass

442.5520 Da

Monoisotopic Mass

442.23554 Da

IUPAC Name

(1S,4S,5S,6S,9S,10R,12R,14R)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-6-yl (3E)-hexa-3,5-dienoate

Traditional Name

(1S,4S,5S,6S,9S,10R,12R,14R)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-6-yl (3E)-hexa-3,5-dienoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2[C@H]([C@@H]3C=C(CO)[C@H](OC(=O)C\C=C\C=C)[C@@]4(O)[C@@H](O)C(C)=C[C@@]14C3=O)C2(C)C

InChI Identifier

InChI=1S/C26H34O6/c1-6-7-8-9-19(28)32-23-16(13-27)11-17-20-18(24(20,4)5)10-15(3)25(22(17)30)12-14(2)21(29)26(23,25)31/h6-8,11-12,15,17-18,20-21,23,27,29,31H,1,9-10,13H2,2-5H3/b8-7+/t15-,17+,18-,20+,21+,23+,25+,26+/m1/s1

InChI Key

AWRJTPFCJAMATC-NGAHXIQYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Ingenane diterpenoid
Fatty acid ester
Fatty acyl
Tertiary alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
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
logP	2.33	ALOGPS
logP	2.1	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.11	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.77 m³·mol⁻¹	ChemAxon
Polarizability	47.6 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	Yes	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

163065509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate (NP0158049)

MOL for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)

3D MOL for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)

3D SDF for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)

3D-SDF for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)

PDB for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)

3D PDB for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)

SMILES for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)

INCHI for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)

Structure for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)

3D Structure for NP0158049 ((1s,4s,5s,6s,9s,10r,12r,14r)-4,5-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-6-yl (3e)-hexa-3,5-dienoate)