NP-MRD: Showing NP-Card for (4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate (NP0145527)

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Record Information

Version

2.0

Created at

2022-09-02 00:44:54 UTC

Updated at

2022-09-02 00:44:55 UTC

NP-MRD ID

NP0145527

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

DTXSID50966985 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. (4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate is found in Euphorbia lathyris. Based on a literature review very few articles have been published on DTXSID50966985.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202442D          

 42 45  0  0  1  0            999 V2000
   11.4396   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1541   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8686   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5831   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2975   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0120   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7265   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4409   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1554   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8699   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5844   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2988   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0133   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7278   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4422   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1567   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1567   -1.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8712   -2.2609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   28.2992   -1.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2439   -2.1641    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
  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
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  9 10  1  0  0  0  0
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 40 42  1  0  0  0  0
M  END

     RDKit          3D

100103  0  0  0  0  0  0  0  0999 V2000
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 34 86  1  0
 41 95  1  0
 41 96  1  0
 41 97  1  0
 42 98  1  0
 42 99  1  0
 42100  1  0
M  END


  Mrv1652309022202442D          

 42 45  0  0  1  0            999 V2000
   11.4396   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1541   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8686   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5831   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2975   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0120   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7265   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4409   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1554   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8699   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5844   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2988   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0133   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7278   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4422   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1567   -1.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1567   -1.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8712   -2.2609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5857   -1.8484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6666   -1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0553   -0.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4781   -0.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9681   -1.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5676   -2.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0801   -1.3979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1856   -2.5357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.8408   -3.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0373   -3.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9012   -4.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1285   -4.6591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3551   -3.0569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6207   -3.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3491   -2.1944    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.6573   -2.6439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8595   -2.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9078   -1.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2790   -0.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4533   -0.8278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.9752   -0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5969   -1.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2992   -1.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2439   -2.1641    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
  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  1  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  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 19 33  1  0  0  0  0
 23 33  1  0  0  0  0
 33 34  1  1  0  0  0
 26 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 23 38  1  0  0  0  0
 38 39  1  6  0  0  0
 36 40  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145527

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)O[C@H]1C(C)=CC23[C@H](C)CC4C([C@@H](C=C(CO)[C@@H](O)[C@]12O)C3=O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C36H58O6/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-29(38)42-33-24(2)22-35-25(3)20-28-30(34(28,4)5)27(32(35)40)21-26(23-37)31(39)36(33,35)41/h21-22,25,27-28,30-31,33,37,39,41H,6-20,23H2,1-5H3/t25-,27-,28?,30?,31-,33+,35?,36+/m1/s1

> <INCHI_KEY>
DOSPRDHNGNPKKJ-OQJUGHSASA-N

> <FORMULA>
C36H58O6

> <MOLECULAR_WEIGHT>
586.854

> <EXACT_MASS>
586.423339588

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
71.67789622981718

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.28

> <JCHEM_LOGP>
7.213721928666669

> <ALOGPS_LOGS>
-6.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.444270004990212

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.091698615344384

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7637287822956065

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
167.61830000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.20e-04 g/l

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

> <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      21.354  -4.220   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.688  -3.450   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.021  -4.220   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.355  -3.450   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.689  -4.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.022  -3.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.356  -4.220   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.690  -3.450   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.023  -4.220   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.357  -3.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.691  -4.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.024  -3.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      37.358  -4.220   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.692  -3.450   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.026  -4.220   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      41.359  -3.450   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      41.359  -1.910   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      42.693  -4.220   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      44.027  -3.450   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.178  -1.914   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.037  -0.880   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.692  -1.613   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      46.607  -2.931   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      47.726  -3.816   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      48.683  -2.609   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      48.880  -4.733   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      48.236  -6.173   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      46.736  -6.639   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      46.482  -8.157   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      45.040  -8.697   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      45.463  -5.706   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      44.092  -6.408   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      45.452  -4.096   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      44.160  -4.935   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      50.138  -3.775   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      50.228  -2.237   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      49.054  -1.161   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      47.513  -1.545   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      46.620  -0.290   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      51.514  -3.084   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      52.825  -2.276   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      52.722  -4.040   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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   33                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   33   38                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   19   23   34                                             
CONECT   34   33                                                            
CONECT   35   26   36   40                                                  
CONECT   36   35   37   40                                                  
CONECT   37   36   38                                                       
CONECT   38   37   23   39                                                  
CONECT   39   38                                                            
CONECT   40   36   35   41   42                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
Ingenol 3-hexadecanoate	MeSH
Ingenol 3-palmitate	MeSH

Chemical Formula

C₃₆H₅₈O₆

Average Mass

586.8540 Da

Monoisotopic Mass

586.42334 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)O[C@H]1C(C)=CC23[C@H](C)CC4C([C@@H](C=C(CO)[C@@H](O)[C@]12O)C3=O)C4(C)C

InChI Identifier

InChI=1S/C36H58O6/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-29(38)42-33-24(2)22-35-25(3)20-28-30(34(28,4)5)27(32(35)40)21-26(23-37)31(39)36(33,35)41/h21-22,25,27-28,30-31,33,37,39,41H,6-20,23H2,1-5H3/t25-,27-,28?,30?,31-,33+,35?,36+/m1/s1

InChI Key

DOSPRDHNGNPKKJ-OQJUGHSASA-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 lathyris	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

Ingenane diterpenoid
Fatty acid ester
Fatty acyl
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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
logP	6.28	ALOGPS
logP	7.21	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	12.09	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	17	ChemAxon
Refractivity	167.62 m³·mol⁻¹	ChemAxon
Polarizability	71.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

142828

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162684

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate (NP0145527)

MOL for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)

3D MOL for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)

3D SDF for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)

3D-SDF for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)

PDB for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)

3D PDB for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)

SMILES for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)

INCHI for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)

Structure for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)

3D Structure for NP0145527 ((4s,5s,6r,9r,14r)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl hexadecanoate)