NP-MRD: Showing NP-Card for {1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate (NP0250306)

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Record Information

Version

2.0

Created at

2022-09-07 13:05:44 UTC

Updated at

2022-09-07 13:05:44 UTC

NP-MRD ID

NP0250306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate

Description

{1-Hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]Pentadeca-3,8-dien-8-yl}methyl benzoate 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. {1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate is found in Euphorbia pannonica. Based on a literature review very few articles have been published on {1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]Pentadeca-3,8-dien-8-yl}methyl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072215052D          

 37 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072215052D          

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    4.5345    1.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0984    1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7742    0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2914    0.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8512   -0.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5015   -0.6719    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  7 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  4 34  1  0  0  0  0
 19 34  1  0  0  0  0
 34 35  1  0  0  0  0
  5 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0250306

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OC12CC(C)C3(O)C4C=C(C)C(=O)C4CC(COC(=O)C4=CC=CC=C4)=CC3C1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O6/c1-17(2)27(33)37-30-15-19(4)31(35)23-12-18(3)25(32)22(23)13-20(14-24(31)26(30)29(30,5)6)16-36-28(34)21-10-8-7-9-11-21/h7-12,14,17,19,22-24,26,35H,13,15-16H2,1-6H3

> <INCHI_KEY>
QMERYCNSXBRAEW-UHFFFAOYSA-N

> <FORMULA>
C31H38O6

> <MOLECULAR_WEIGHT>
506.639

> <EXACT_MASS>
506.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.57889470096822

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-8-yl}methyl benzoate

> <JCHEM_LOGP>
5.294187376

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.19734081071973

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.001343495166768

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2356059084407764

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
141.23440000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-8-yl}methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      14.118   2.094   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.842   1.232   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.394   1.758   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.447   0.544   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.309  -0.732   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.848  -2.201   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.412  -2.758   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.290  -4.293   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.559  -5.166   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.437  -6.701   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.046  -7.363   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.705  -7.574   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.096  -6.912   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.364  -7.786   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.242  -9.321   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.852  -9.983   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.583  -9.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.082  -1.982   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.859  -0.458   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.359  -0.108   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.860   0.241   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.570   1.082   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.255  -1.175   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.912   1.365   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.788   2.418   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.137   3.918   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.013   4.970   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.611   4.365   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.960   5.865   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.735   3.312   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.965   2.489   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.464   2.140   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.517   3.264   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.912   0.666   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.877   1.866   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.789  -0.307   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.003  -1.254   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   34                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    7   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   20   25   31                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   24   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    4   19   35                                             
CONECT   35   34                                                            
CONECT   36    5    2   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
{1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0,.0,]pentadeca-3,8-dien-8-yl}methyl benzoic acid	Generator

Chemical Formula

C₃₁H₃₈O₆

Average Mass

506.6390 Da

Monoisotopic Mass

506.26684 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OC12CC(C)C3(O)C4C=C(C)C(=O)C4CC(COC(=O)C4=CC=CC=C4)=CC3C1C2(C)C

InChI Identifier

InChI=1S/C31H38O6/c1-17(2)27(33)37-30-15-19(4)31(35)23-12-18(3)25(32)22(23)13-20(14-24(31)26(30)29(30,5)6)16-36-28(34)21-10-8-7-9-11-21/h7-12,14,17,19,22-24,26,35H,13,15-16H2,1-6H3

InChI Key

QMERYCNSXBRAEW-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
Euphorbia pannonica	LOTUS Database	35616633

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

Tigliane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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

162879744

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate (NP0250306)

MOL for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)

3D MOL for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)

3D SDF for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)

3D-SDF for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)

PDB for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)

3D PDB for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)

SMILES for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)

INCHI for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)

Structure for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)

3D Structure for NP0250306 ({1-hydroxy-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-8-yl}methyl benzoate)