NP-MRD: Showing NP-Card for 13-Benzoyloxy ingenol (NP0332075)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2023-11-02 00:00:47 UTC

Updated at

2024-09-03 04:17:53 UTC

NP-MRD ID

NP0332075

Natural Product DOI

https://doi.org/10.57994/1203

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-Benzoyloxy ingenol

Description

Based on a literature review very few articles have been published on 13-Benzoyloxy ingenol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 11022300002D          

 36 40  0  0  1  0            999 V2000
    3.8237   -0.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3226   -0.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458   -1.3568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6051   -1.8527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -2.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943   -2.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -3.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914   -3.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -1.9066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3863   -2.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -1.0567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4493   -1.5389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3378   -0.7935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6589   -1.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3684    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    0.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689    0.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.4147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1861    0.3443    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6950    1.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0111    0.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6593    0.0292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1496    0.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8200    1.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3103    2.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807    2.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4710    3.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907    3.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6203    2.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1300    2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0003    1.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6109   -0.7944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0653   -1.4829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484   -0.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9952   -0.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    0.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  6  1  0  0  0  0
  9 10  1  1  0  0  0
 11  9  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 17  1  0  0  0  0
 11 18  1  0  0  0  0
 18  2  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 24 31  2  0  0  0  0
 32 22  1  0  0  0  0
 32  3  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END


  Mrv2104 11022300002D          

 36 40  0  0  1  0            999 V2000
    3.8237   -0.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3226   -0.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458   -1.3568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6051   -1.8527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -2.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943   -2.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -3.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914   -3.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1211   -1.9066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3863   -2.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -1.0567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4493   -1.5389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3378   -0.7935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6589   -1.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3684    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    0.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689    0.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141   -0.4147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1861    0.3443    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6950    1.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0111    0.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6593    0.0292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1496    0.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8200    1.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3103    2.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807    2.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4710    3.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907    3.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6203    2.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1300    2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0003    1.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6109   -0.7944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0653   -1.4829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484   -0.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9952   -0.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    0.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  6  1  0  0  0  0
  9 10  1  1  0  0  0
 11  9  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 17  1  0  0  0  0
 11 18  1  0  0  0  0
 18  2  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 24 31  2  0  0  0  0
 32 22  1  0  0  0  0
 32  3  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@]3([H])C=C(CO)[C@@H](O)[C@]4(O)[C@@H](O)C(C)=C[C@]4([C@H](C)C[C@@]1(OC(=O)C1=CC=CC=C1)C2(C)C)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O7/c1-14-11-25-15(2)12-26(34-23(32)16-8-6-5-7-9-16)19(24(26,3)4)18(22(25)31)10-17(13-28)21(30)27(25,33)20(14)29/h5-11,15,18-21,28-30,33H,12-13H2,1-4H3/t15-,18+,19-,20+,21-,25+,26+,27-/m1/s1

> <INCHI_KEY>
BCOXPWXQEFQNOV-OALUNMQBSA-N

> <FORMULA>
C27H32O7

> <MOLECULAR_WEIGHT>
468.546

> <EXACT_MASS>
468.21480337

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.75750513670668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.70662184

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.715409716102679

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.135573801391981

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7637446495038036

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
125.29999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-NOV-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-NOV-23         0                                  
HETATM    1  O   UNK     0       7.138  -0.404   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.202  -1.628   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.365  -2.533   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       8.596  -3.458   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       6.710  -3.998   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.216  -4.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.970  -5.995   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.531  -6.542   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.959  -3.559   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.588  -4.259   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.955  -1.973   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.705  -2.873   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.497  -1.481   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.230  -2.356   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.554   0.058   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.347   1.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.049   0.468   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.066  -0.774   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.947   0.643   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.031   1.880   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.487   1.054   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.697   0.055   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.613   1.293   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.997   2.705   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.913   3.944   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.297   5.355   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.212   6.594   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.743   6.421   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.358   5.009   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.443   3.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.467   2.878   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.607  -1.483   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0       9.455  -2.768   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0       9.984  -0.792   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.191  -1.748   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.295   0.015   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4    5   32                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   11    2   19                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   32   34                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   24                                                            
CONECT   32   22    3   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   22   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₇

Average Mass

468.5460 Da

Monoisotopic Mass

468.21480 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@]3([H])C=C(CO)[C@@H](O)[C@]4(O)[C@@H](O)C(C)=C[C@]4([C@H](C)C[C@@]1(OC(=O)C1=CC=CC=C1)C2(C)C)C3=O

InChI Identifier

InChI=1S/C27H32O7/c1-14-11-25-15(2)12-26(34-23(32)16-8-6-5-7-9-16)19(24(26,3)4)18(22(25)31)10-17(13-28)21(30)27(25,33)20(14)29/h5-11,15,18-21,28-30,33H,12-13H2,1-4H3/t15-,18+,19-,20+,21-,25+,26+,27-/m1/s1

InChI Key

BCOXPWXQEFQNOV-OALUNMQBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
Long chain fatty alcohol
Fatty alcohol ester
Benzoate ester
Fatty alcohol
Benzoic acid or derivatives
Benzoyl
Fatty acid ester
Fatty acyl
Benzenoid
Beta-hydroxy ketone
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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
logP	1.71	ChemAxon
pKa (Strongest Acidic)	12.14	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	125.3 m³·mol⁻¹	ChemAxon
Polarizability	49.76 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 13-Benzoyloxy ingenol (NP0332075)

MOL for NP0332075 (13-Benzoyloxy ingenol)

3D MOL for NP0332075 (13-Benzoyloxy ingenol)

3D SDF for NP0332075 (13-Benzoyloxy ingenol)

3D-SDF for NP0332075 (13-Benzoyloxy ingenol)

PDB for NP0332075 (13-Benzoyloxy ingenol)

3D PDB for NP0332075 (13-Benzoyloxy ingenol)

SMILES for NP0332075 (13-Benzoyloxy ingenol)

INCHI for NP0332075 (13-Benzoyloxy ingenol)

Structure for NP0332075 (13-Benzoyloxy ingenol)

3D Structure for NP0332075 (13-Benzoyloxy ingenol)