NP-MRD: Showing NP-Card for (1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one (NP0250849)

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Record Information

Version

2.0

Created at

2022-09-07 13:49:51 UTC

Updated at

2022-09-07 13:49:51 UTC

NP-MRD ID

NP0250849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one

Description

Ingenol 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. (1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one is found in Euphorbia esula, Euphorbia ingens, Euphorbia lathyris, Euphorbia segetalis and Euphorbia tirucalli. (1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one was first documented in 2022 (PMID: 35891551). Based on a literature review a small amount of articles have been published on ingenol (PMID: 35889247) (PMID: 35733180) (PMID: 35724704) (PMID: 35721664).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072215492D          

 25 28  0  0  1  0            999 V2000
    0.3613   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956   -0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190   -1.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9381   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764   -2.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2647   -2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725   -3.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -3.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114   -4.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697   -2.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -3.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271   -1.8217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0550   -2.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496   -1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2533   -1.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -1.5430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2412   -0.7181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5885   -0.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2661    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489   -1.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6323   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171   -1.6261    0.0000 C   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  6  0  0  0
  5  6  2  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -2.8827    0.1014    2.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1542   -0.1989    1.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535   -0.1200    1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6787   -0.5217   -0.1816 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3234    0.1064   -1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2950   -0.1777   -2.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973    1.0532   -0.4833 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4841    2.0926    0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    2.1358    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946    3.1766    1.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0635    4.0971    0.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9478    1.4646   -0.4126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1943    2.1207   -1.6482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234   -0.0062   -0.7547 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2173   -0.2904   -2.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068   -0.6621    0.2463 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0310   -1.9975    0.0984 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644    0.2364    0.3775 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1581   -1.2043   -0.2115 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1279   -1.9161    0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2729   -1.9367   -0.1244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2340   -2.6828   -1.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3574   -0.5140    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    0.0154   -1.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2032   -1.0532    1.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1777    0.4730    3.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4243   -0.8205    3.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6618    0.8442    2.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2161    0.2209    2.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8959    1.4889   -1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295    2.8853    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494    3.7183    1.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801    2.7509    1.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832    4.3710   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958    1.7062    0.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7795    1.5958   -2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936   -0.1984   -2.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521   -0.0886    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0491   -2.2959   -0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820    0.3432    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680   -1.3032   -1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9540   -1.5062    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006   -2.9920    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8641   -2.5322    0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -3.7228   -1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7897   -2.8644   -1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764   -2.1852   -2.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2482   -0.3851   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7703   -0.3027   -1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2200    1.1311   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1432   -1.4978    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6689   -1.8848    1.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4423   -0.2676    1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 16  2  1  0
  2  1  1  0
  2  3  2  0
  4  3  1  1
  4  5  1  0
  5  6  2  0
 18 23  1  0
 23 24  1  0
 23 25  1  0
  4 21  1  0
 23 19  1  0
  5  7  1  0
  4 14  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 21 44  1  1
 20 42  1  0
 20 43  1  0
 19 41  1  6
 18 40  1  1
  7 30  1  6
  8 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  1
 13 36  1  0
 15 37  1  0
 16 38  1  1
 17 39  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
M  END


  Mrv1652309072215492D          

 25 28  0  0  1  0            999 V2000
    0.3613   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956   -0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190   -1.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9381   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764   -2.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2647   -2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725   -3.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -3.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114   -4.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697   -2.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -3.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271   -1.8217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0550   -2.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496   -1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2533   -1.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -1.5430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2412   -0.7181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5885   -0.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2661    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489   -1.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6323   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171   -1.6261    0.0000 C   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  6  0  0  0
  5  6  2  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C[C@H]2[C@H]([C@@H]3C=C(CO)C(O)[C@]4(O)C(O)C(C)=C[C@@]14C3=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10?,12-,13-,14-,15?,16?,19-,20+/m0/s1

> <INCHI_KEY>
VEBVPUXQAPLADL-XYMGVRDUSA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.439

> <EXACT_MASS>
348.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
73.41061817251737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.2926680263333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.016893548529097

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.004417870063111

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7637285942320906

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
94.02689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

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

> <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       0.675  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.858  -1.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.359  -0.910   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.329  -2.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.484  -3.024   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.389  -1.778   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.676  -3.891   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.094  -5.357   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.615  -5.886   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.426  -7.414   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.008  -8.015   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.304  -5.009   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.964  -5.768   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.224  -3.400   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.969  -4.293   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.773  -2.816   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.473  -3.642   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.892  -2.880   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.917  -1.341   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.698  -0.315   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.175  -0.764   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.230   0.452   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.238  -2.132   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.514  -1.269   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.485  -3.035   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   21                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4   15   16                                             
CONECT   15   14                                                            
CONECT   16   14    2   17                                                  
CONECT   17   16                                                            
CONECT   18    7   19   23                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21                                                            
CONECT   23   19   18   24   25                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₅

Average Mass

348.4390 Da

Monoisotopic Mass

348.19367 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1C[C@H]2[C@H]([C@@H]3C=C(CO)C(O)[C@]4(O)C(O)C(C)=C[C@@]14C3=O)C2(C)C

InChI Identifier

InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10?,12-,13-,14-,15?,16?,19-,20+/m0/s1

InChI Key

VEBVPUXQAPLADL-XYMGVRDUSA-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 esula	LOTUS Database	35616633
Euphorbia ingens	LOTUS Database	35616633
Euphorbia lathyris	LOTUS Database	35616633
Euphorbia segetalis	LOTUS Database	35616633
Euphorbia tirucalli	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
Tertiary alcohol
Secondary alcohol
Ketone
Polyol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003439

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ingenol mebutate

METLIN ID

Not Available

PubChem Compound

137795436

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Curty G, Iniguez LP, Soares MA, Nixon DF, de Mulder Rougvie M: Off-Target Effect of Activation of NF-kappaB by HIV Latency Reversal Agents on Transposable Elements Expression. Viruses. 2022 Jul 20;14(7):1571. doi: 10.3390/v14071571. [PubMed:35891551 ]
Sultana A, Hossain MJ, Kuddus MR, Rashid MA, Zahan MS, Mitra S, Roy A, Alam S, Sarker MMR, Naina Mohamed I: Ethnobotanical Uses, Phytochemistry, Toxicology, and Pharmacological Properties of Euphorbia neriifolia Linn. against Infectious Diseases: A Comprehensive Review. Molecules. 2022 Jul 8;27(14):4374. doi: 10.3390/molecules27144374. [PubMed:35889247 ]
da Costa LC, Bomfim LM, Dittz UVT, Velozo CA, da Cunha RD, Tanuri A: Repression of HIV-1 reactivation mediated by CRISPR/dCas9-KRAB in lymphoid and myeloid cell models. Retrovirology. 2022 Jun 22;19(1):12. doi: 10.1186/s12977-022-00600-9. [PubMed:35733180 ]
Hsieh YY, Cheng YW, Wei PL, Yang PM: Repurposing of ingenol mebutate for treating human colorectal cancer by targeting S100 calcium-binding protein A4 (S100A4). Toxicol Appl Pharmacol. 2022 Aug 15;449:116134. doi: 10.1016/j.taap.2022.116134. Epub 2022 Jun 18. [PubMed:35724704 ]
Lu P, Yang J, Yang X, Liang Z, Wang J, Wang Y, Zhao L, Pan H, Shen X, Zhu Y, Xun J, Lu H, Zhu H: EK-16A liposomes enhance HIV replication in ACH2 or J-Lat 10.6 cell engrafted NSG mice. Nanotheranostics. 2022 Mar 21;6(3):325-336. doi: 10.7150/ntno.69259. eCollection 2022. [PubMed:35721664 ]
LOTUS database [Link]

Showing NP-Card for (1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one (NP0250849)

MOL for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D MOL for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D SDF for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D-SDF for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

PDB for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D PDB for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

SMILES for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

INCHI for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

Structure for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D Structure for NP0250849 ((1s,5r,9s,10r,12s)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)