NP-MRD: Showing NP-Card for 12-O-Tiglylphorbol-13-isobutyrate (NP0138162)

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Record Information

Version

2.0

Created at

2022-05-31 17:00:43 UTC

Updated at

2022-05-31 17:00:43 UTC

NP-MRD ID

NP0138162

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-O-Tiglylphorbol-13-isobutyrate

Description

12-O-Tiglylphorbol-13-isobutyrate belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. 12-O-Tiglylphorbol-13-isobutyrate was first documented in 2017 (PMID: 28499304). Based on a literature review very few articles have been published on 12-O-Tiglylphorbol-13-isobutyrate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312219002D          

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  5  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
  8 31  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C(C)(C)C12OC(=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O8/c1-9-15(4)25(33)36-23-17(6)28(35)19(21-26(7,8)29(21,23)37-24(32)14(2)3)11-18(13-30)12-27(34)20(28)10-16(5)22(27)31/h9-11,14,17,19-21,23,30,34-35H,12-13H2,1-8H3

> <INCHI_KEY>
MVWXLRYZCZSBKW-UHFFFAOYSA-N

> <FORMULA>
C29H40O8

> <MOLECULAR_WEIGHT>
516.631

> <EXACT_MASS>
516.272318248

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.198801684139454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl 2-methylbut-2-enoate

> <JCHEM_LOGP>
3.116702025999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.93321060137298

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.570369319392295

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7316135464920155

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
137.9601

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-13-[(2-methylpropanoyl)oxy]-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  C   UNK     0       5.968   6.046   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.415   4.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.363   3.448   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.863   3.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.810   1.975   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.310   1.625   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.758   0.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.205  -0.623   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.705  -0.973   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.757   0.152   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.152  -2.446   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.118  -1.246   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.687  -2.568   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.635  -1.354   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -1.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.358  -1.018   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.029  -3.419   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.243  -4.367   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.549  -3.844   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.625  -4.946   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.089  -5.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.652  -5.870   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.530  -7.405   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.140  -8.067   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.322  -5.094   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.100  -3.570   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.600  -3.221   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.100  -2.871   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.495  -4.288   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.810  -2.030   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.152  -1.747   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.028  -0.695   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.378   0.805   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.641   1.686   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.254   1.858   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.780   1.410   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.603   3.357   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   31                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   26                                             
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   11   27                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28    8   27   32                                             
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
12-O-Tiglylphorbol-13-isobutyric acid	Generator

Chemical Formula

C₂₉H₄₀O₈

Average Mass

516.6310 Da

Monoisotopic Mass

516.27232 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

92214-54-5

SMILES

CC=C(C)C(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C(C)(C)C12OC(=O)C(C)C

InChI Identifier

InChI=1S/C29H40O8/c1-9-15(4)25(33)36-23-17(6)28(35)19(21-26(7,8)29(21,23)37-24(32)14(2)3)11-18(13-30)12-27(34)20(28)10-16(5)22(27)31/h9-11,14,17,19-21,23,30,34-35H,12-13H2,1-8H3

InChI Key

MVWXLRYZCZSBKW-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Phorbol esters

Alternative Parents

Substituents

Phorbol ester
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
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

78151410

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Du Q, Zhao Y, Liu H, Tang C, Zhang M, Ke C, Ye Y: Isolation and Structure Characterization of Cytotoxic Phorbol Esters from the Seeds of Croton tiglium. Planta Med. 2017 Nov;83(17):1361-1367. doi: 10.1055/s-0043-110227. Epub 2017 May 12. [PubMed:28499304 ]

Showing NP-Card for 12-O-Tiglylphorbol-13-isobutyrate (NP0138162)

MOL for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)

3D MOL for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)

3D SDF for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)

3D-SDF for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)

PDB for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)

3D PDB for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)

SMILES for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)

INCHI for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)

Structure for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)

3D Structure for NP0138162 (12-O-Tiglylphorbol-13-isobutyrate)