NP-MRD: Showing NP-Card for 12-O-tiglylporbol-13-propionate (NP0043373)

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Record Information

Version

1.0

Created at

2021-06-21 00:47:54 UTC

Updated at

2021-06-30 00:19:01 UTC

NP-MRD ID

NP0043373

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-O-tiglylporbol-13-propionate

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2375794 belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. 12-O-tiglylporbol-13-propionate is found in Croton tiglium. It was first documented in 2013 (Zhang, X. -L., et al.). Based on a literature review very few articles have been published on CHEMBL2375794.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102473D          

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M  END

     RDKit          3D

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 27 31  1  0
 35 36  1  0
 28 27  1  0
 33 34  2  0
 31 28  1  0
  2  1  1  0
 14 51  1  0
 18 55  1  0
 18 56  1  0
  9 45  1  1
 25 61  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
 20 57  1  0
  8 44  1  6
 12 49  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  0
 30 68  1  0
 30 69  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 10 46  1  0
 10 47  1  0
 10 48  1  0
  4 41  1  0
  4 42  1  0
  4 43  1  0
  2 40  1  0
 35 70  1  0
 35 71  1  0
 36 72  1  0
 36 73  1  0
 36 74  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
M  END


  Mrv1652306212102473D          

 74 77  0  0  0  0            999 V2000
   -5.0160    3.1082    1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6804    2.4912    0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    3.0979    0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4218    4.5600   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920    2.3259    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2650    2.8442   -0.3413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    1.0165    0.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2750    0.1791    0.2543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7412   -1.2440   -0.1706 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1550   -1.1528   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3219   -2.3472    0.1597 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5501   -2.0256   -0.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5258   -2.3481    1.7295 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3569   -3.4970    2.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0024   -4.8016    2.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969   -5.8068    2.9934 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5092   -6.6183    2.0043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2451   -5.4168    1.6702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9634   -4.6042    0.5765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0116   -3.8045    1.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533   -5.4896   -0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4427   -6.3852   -0.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3407   -5.0669   -1.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653   -5.6710   -3.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4242   -4.0992   -1.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0230   -3.8134   -0.3074 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9806   -0.9933    2.2381 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0285   -0.0303    2.9496 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4304   -0.3437    3.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    0.7400    4.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    0.2714    1.5335 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4919    1.3774    1.5102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120    1.2431    0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9220    0.2149    0.1558 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3947    2.5312    0.7562 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6275    2.4538   -0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2799    2.9637    2.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6859   -5.3338    3.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9488   -5.6595    2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0504   -5.5301   -3.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -5.2173   -3.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -6.7445   -3.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0426   -3.6139   -2.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9947   -4.3366   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0189   -1.0113    2.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -0.9861    4.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868    0.5817    3.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9178   -0.8470    2.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1560    1.7309    4.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    0.8755    4.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7440    3.3362    0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6961    2.7437    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3037    1.6611    0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542    2.2406   -1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733    3.4020   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 26  1  0  0  0  0
 14 15  2  0  0  0  0
 18 15  1  0  0  0  0
  8  7  1  0  0  0  0
 11 13  1  0  0  0  0
 26 62  1  6  0  0  0
 13 14  1  0  0  0  0
 11 12  1  6  0  0  0
 26 25  1  0  0  0  0
 31 32  1  1  0  0  0
 25 23  2  0  0  0  0
 27 63  1  1  0  0  0
 23 21  1  0  0  0  0
 28 29  1  6  0  0  0
 21 19  1  0  0  0  0
 28 30  1  0  0  0  0
 26 11  1  0  0  0  0
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 16 17  1  0  0  0  0
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  9 10  1  0  0  0  0
 21 22  2  0  0  0  0
  7  5  1  0  0  0  0
 11  9  1  0  0  0  0
  5  3  1  0  0  0  0
 19 20  1  1  0  0  0
  3  4  1  0  0  0  0
 13 27  1  0  0  0  0
  5  6  2  0  0  0  0
 13 50  1  1  0  0  0
  3  2  2  0  0  0  0
 31  8  1  0  0  0  0
 32 33  1  0  0  0  0
  8  9  1  0  0  0  0
 33 35  1  0  0  0  0
 27 31  1  0  0  0  0
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 31 28  1  0  0  0  0
  2  1  1  0  0  0  0
 14 51  1  0  0  0  0
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 35 70  1  0  0  0  0
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  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])[C@@]2([H])[C@@]3([H])[C@@](OC(=O)C([H])([H])C([H])([H])[H])([C@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@@]([H])(C([H])([H])[H])[C@]2(O[H])[C@]2([H])C([H])=C(C(=O)[C@@]2(O[H])C1([H])[H])C([H])([H])[H])C3(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O8/c1-8-14(3)24(32)35-23-16(5)27(34)18(21-25(6,7)28(21,23)36-20(30)9-2)11-17(13-29)12-26(33)19(27)10-15(4)22(26)31/h8,10-11,16,18-19,21,23,29,33-34H,9,12-13H2,1-7H3/b14-8+/t16-,18+,19-,21-,23-,26-,27-,28-/m1/s1

> <INCHI_KEY>
WZPQMMCMYVTCRV-IFFRIBCBSA-N

> <FORMULA>
C28H38O8

> <MOLECULAR_WEIGHT>
502.604

> <EXACT_MASS>
502.256668184

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.62579016626956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-(propanoyloxy)tetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.5737157476666663

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.933210604204145

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.57036931956521

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7316135464912623

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
133.38559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-(propanoyloxy)tetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 74 77  0  0  0  0  0  0  0  0999 V2000
   -5.0160    3.1082    1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6804    2.4912    0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    3.0979    0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4218    4.5600   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920    2.3259    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4445    1.0165    0.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2750    0.1791    0.2543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7412   -1.2440   -0.1706 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1550   -1.1528   -1.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3219   -2.3472    0.1597 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5501   -2.0256   -0.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0024   -4.8016    2.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969   -5.8068    2.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9806   -0.9933    2.2381 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0285   -0.0303    2.9496 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.9220    0.2149    0.1558 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6275    2.4538   -0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0504   -5.5301   -3.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -5.2173   -3.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -6.7445   -3.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5429   -0.9861    4.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3542    2.2406   -1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733    3.4020   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  1  0
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M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.016   3.108   1.013  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.680   2.491   0.742  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.559   3.098   0.299  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.422   4.560  -0.018  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.292   2.326   0.075  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.265   2.844  -0.341  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.444   1.016   0.389  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.275   0.179   0.254  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.741  -1.244  -0.171  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.155  -1.153  -1.651  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.322  -2.347   0.160  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.550  -2.026  -0.528  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.526  -2.348   1.730  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.357  -3.497   2.279  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.002  -4.802   2.310  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.897  -5.807   2.993  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.509  -6.618   2.004  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.245  -5.417   1.670  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.963  -4.604   0.577  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.012  -3.805   1.135  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.653  -5.490  -0.452  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.443  -6.385  -0.181  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.341  -5.067  -1.830  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.965  -5.671  -3.024  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.424  -4.099  -1.720  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.023  -3.813  -0.307  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.981  -0.993   2.238  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.029  -0.030   2.950  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.430  -0.344   3.176  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.617   0.740   4.116  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.545   0.271   1.534  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.492   1.377   1.510  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.612   1.243   0.744  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.922   0.215   0.156  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.395   2.531   0.756  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.628   2.454  -0.127  0.00  0.00           C+0
HETATM   37  H   UNK     0      -5.280   2.964   2.066  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.778   2.614   0.402  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.063   4.177   0.801  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.665   1.420   0.941  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.159   4.697  -1.072  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.633   5.009   0.596  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.332   5.134   0.165  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.343   0.557  -0.572  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.667  -1.476   0.365  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.284  -1.135  -2.314  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.737  -0.245  -1.847  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.807  -1.982  -1.933  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.007  -1.266  -0.111  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.451  -2.502   2.195  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.300  -3.212   2.745  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.316  -6.446   3.666  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.686  -5.334   3.587  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.979  -6.016   1.401  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.056  -6.375   1.226  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.949  -5.660   2.477  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.685  -4.429   1.471  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.050  -5.530  -3.003  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.585  -5.217  -3.945  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.756  -6.745  -3.067  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.043  -3.614  -2.569  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.995  -4.337  -0.297  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.019  -1.011   2.556  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.543  -0.986   4.056  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.987   0.582   3.361  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.918  -0.847   2.342  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.432   0.207   5.055  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.156   1.731   4.185  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.700   0.876   4.026  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.744   3.336   0.399  0.00  0.00           H+0
HETATM   71  H   UNK     0       3.696   2.744   1.787  0.00  0.00           H+0
HETATM   72  H   UNK     0       5.304   1.661   0.211  0.00  0.00           H+0
HETATM   73  H   UNK     0       4.354   2.241  -1.165  0.00  0.00           H+0
HETATM   74  H   UNK     0       5.173   3.402  -0.104  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    3    1   40                                                  
CONECT    3    5    4    2                                                  
CONECT    4    3   41   42   43                                             
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    7   31    9   44                                             
CONECT    9   10   11    8   45                                             
CONECT   10    9   46   47   48                                             
CONECT   11   13   12   26    9                                             
CONECT   12   11   49                                                       
CONECT   13   11   14   27   50                                             
CONECT   14   15   13   51                                                  
CONECT   15   14   18   16                                                  
CONECT   16   15   17   52   53                                             
CONECT   17   16   54                                                       
CONECT   18   15   19   55   56                                             
CONECT   19   26   21   18   20                                             
CONECT   20   19   57                                                       
CONECT   21   23   19   22                                                  
CONECT   22   21                                                            
CONECT   23   25   21   24                                                  
CONECT   24   23   58   59   60                                             
CONECT   25   26   23   61                                                  
CONECT   26   19   62   25   11                                             
CONECT   27   63   13   31   28                                             
CONECT   28   29   30   27   31                                             
CONECT   29   28   64   65   66                                             
CONECT   30   28   67   68   69                                             
CONECT   31   32    8   27   28                                             
CONECT   32   31   33                                                       
CONECT   33   32   35   34                                                  
CONECT   34   33                                                            
CONECT   35   33   36   70   71                                             
CONECT   36   35   72   73   74                                             
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    2                                                            
CONECT   41    4                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   12                                                            
CONECT   50   13                                                            
CONECT   51   14                                                            
CONECT   52   16                                                            
CONECT   53   16                                                            
CONECT   54   17                                                            
CONECT   55   18                                                            
CONECT   56   18                                                            
CONECT   57   20                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   26                                                            
CONECT   63   27                                                            
CONECT   64   29                                                            
CONECT   65   29                                                            
CONECT   66   29                                                            
CONECT   67   30                                                            
CONECT   68   30                                                            
CONECT   69   30                                                            
CONECT   70   35                                                            
CONECT   71   35                                                            
CONECT   72   36                                                            
CONECT   73   36                                                            
CONECT   74   36                                                            
MASTER        0    0    0    0    0    0    0    0   74    0  154    0
END

RDKit          3D

74 77  0  0  0  0  0  0  0  0999 V2000
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    1.3159   -6.4458    3.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859   -5.3338    3.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9788   -6.0158    1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561   -6.3752    1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -5.6595    2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848   -4.4289    1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504   -5.5301   -3.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -5.2173   -3.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -6.7445   -3.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0426   -3.6139   -2.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9947   -4.3366   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0189   -1.0113    2.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -0.9861    4.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868    0.5817    3.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9178   -0.8470    2.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4319    0.2071    5.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1560    1.7309    4.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    0.8755    4.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7440    3.3362    0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6961    2.7437    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3037    1.6611    0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542    2.2406   -1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733    3.4020   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 26  1  0
 14 15  2  0
 18 15  1  0
  8  7  1  0
 11 13  1  0
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 13 14  1  0
 11 12  1  6
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 31 32  1  1
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  7  5  1  0
 11  9  1  0
  5  3  1  0
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  3  4  1  0
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  5  6  2  0
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  3  2  2  0
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  8  9  1  0
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  9 45  1  1
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  4 41  1  0
  4 42  1  0
  4 43  1  0
  2 40  1  0
 35 70  1  0
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 36 72  1  0
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 36 74  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₈

Average Mass

502.6040 Da

Monoisotopic Mass

502.25667 Da

IUPAC Name

(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-(propanoyloxy)tetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-(propanoyloxy)tetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C([H])[C@@]2([H])[C@@]3([H])[C@@](OC(=O)C([H])([H])C([H])([H])[H])([C@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@@]([H])(C([H])([H])[H])[C@]2(O[H])[C@]2([H])C([H])=C(C(=O)[C@@]2(O[H])C1([H])[H])C([H])([H])[H])C3(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C28H38O8/c1-8-14(3)24(32)35-23-16(5)27(34)18(21-25(6,7)28(21,23)36-20(30)9-2)11-17(13-29)12-26(33)19(27)10-15(4)22(26)31/h8,10-11,16,18-19,21,23,29,33-34H,9,12-13H2,1-7H3/b14-8+/t16-,18+,19-,21-,23-,26-,27-,28-/m1/s1

InChI Key

WZPQMMCMYVTCRV-IFFRIBCBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Croton tiglium	JEOL database	Zhang, X. -L., et al, J. Nat. Prod. 76, 858 (2013)

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
logP	2.74	ALOGPS
logP	2.57	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	133.39 m³·mol⁻¹	ChemAxon
Polarizability	54.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

30811950

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73348804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, X. -L., et al. (2013). Zhang, X. -L., et al, J. Nat. Prod. 76, 858 (2013). J. Nat. Prod..

Showing NP-Card for 12-O-tiglylporbol-13-propionate (NP0043373)

MOL for NP0043373 (12-O-tiglylporbol-13-propionate)

3D MOL for NP0043373 (12-O-tiglylporbol-13-propionate)

3D SDF for NP0043373 (12-O-tiglylporbol-13-propionate)

3D-SDF for NP0043373 (12-O-tiglylporbol-13-propionate)

PDB for NP0043373 (12-O-tiglylporbol-13-propionate)

3D PDB for NP0043373 (12-O-tiglylporbol-13-propionate)

SMILES for NP0043373 (12-O-tiglylporbol-13-propionate)

INCHI for NP0043373 (12-O-tiglylporbol-13-propionate)

Structure for NP0043373 (12-O-tiglylporbol-13-propionate)

3D Structure for NP0043373 (12-O-tiglylporbol-13-propionate)