NP-MRD: Showing NP-Card for 16-hydroxyphorbol-16-acetate (NP0038645)

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Record Information

Version

2.0

Created at

2021-06-20 21:16:47 UTC

Updated at

2021-06-30 00:11:32 UTC

NP-MRD ID

NP0038645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-hydroxyphorbol-16-acetate

Provided By

JEOL Database JEOL Logo

Description

16-Hydroxyphorbol-16-acetate 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. 16-hydroxyphorbol-16-acetate is found in Sapium insigne (ROYLE) BENTH. ex HOOK. fil. 16-hydroxyphorbol-16-acetate was first documented in 2009 (PMID: 19881284). Based on a literature review very few articles have been published on 16-Hydroxyphorbol-16-acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123163D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202123163D          

 60 63  0  0  0  0            999 V2000
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   -2.5803    2.6376   -1.0056 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9499    3.5300    3.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    3.6778    2.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375    0.6158    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060    1.7574    1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1929    0.4537    2.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524    2.0898    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978   -0.2947    0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2350    0.1844    1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7452   -3.2896    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226   -2.6104    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -1.3938    3.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046   -3.3417   -0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6959   -3.4250    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707   -2.9611   -0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8394   -2.3101   -5.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4017   -3.4127   -5.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3143   -3.8585   -4.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -0.3733   -3.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -0.9155   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    1.2393   -1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738    0.2614   -1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -0.0328   -3.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427    1.4751   -3.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    1.5097   -3.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    3.0731   -1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6768    3.5195   -0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004    4.2080   -0.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  2  0  0  0  0
 19 17  1  0  0  0  0
 17 15  1  0  0  0  0
  8 29  1  0  0  0  0
  6  8  1  0  0  0  0
 29  6  1  0  0  0  0
 23  9  1  0  0  0  0
 25 23  1  0  0  0  0
  9 10  1  0  0  0  0
 23 22  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4  2  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 22 52  1  1  0  0  0
 15 14  1  0  0  0  0
 23 24  1  1  0  0  0
 15 22  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 29 30  1  1  0  0  0
  9  8  1  0  0  0  0
  8 39  1  1  0  0  0
  6  5  1  1  0  0  0
 29 27  1  0  0  0  0
 15 16  1  1  0  0  0
  5  4  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
 27 28  1  0  0  0  0
 22 21  1  0  0  0  0
  2  3  2  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 25 54  1  1  0  0  0
 27 58  1  6  0  0  0
  9 40  1  6  0  0  0
 10 41  1  0  0  0  0
 14 45  1  0  0  0  0
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 21 51  1  0  0  0  0
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 12 42  1  0  0  0  0
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 13 44  1  0  0  0  0
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 26 57  1  0  0  0  0
 30 60  1  0  0  0  0
 16 47  1  0  0  0  0
  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
 28 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038645

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O8/c1-10-5-15-20(27,17(10)25)7-13(8-23)6-14-16-19(4,9-30-12(3)24)22(16,29)18(26)11(2)21(14,15)28/h5-6,11,14-16,18,23,26-29H,7-9H2,1-4H3/t11-,14+,15-,16-,18-,19-,20-,21-,22-/m1/s1

> <INCHI_KEY>
VTPNUNULKVERON-APOWTESASA-N

> <FORMULA>
C22H30O8

> <MOLECULAR_WEIGHT>
422.474

> <EXACT_MASS>
422.194067926

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.91633075922745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2S,6R,10S,11R,12S,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-12-yl]methyl acetate

> <ALOGPS_LOGP>
-0.05

> <JCHEM_LOGP>
-1.6205284906666666

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.192325003388678

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.471646993380986

> <JCHEM_PKA_STRONGEST_BASIC>
-2.731613727731631

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
106.7036

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2S,6R,10S,11R,12S,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-12-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
   -0.5783    1.7817    6.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0943    2.1035    1.6983 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2905    1.1805    1.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2444    1.6828    1.0868 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4690    0.3095    0.4763 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6415   -0.4227    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -1.7329    1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -2.3658    1.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728   -1.5043    2.8173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2962   -2.7392    0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4418   -2.1939   -1.0991 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9225   -2.0585   -0.7018 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1760   -4.3233   -2.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6909   -2.3985   -3.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067   -3.0273   -4.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993   -1.1466   -3.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415   -0.9118   -1.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5061    0.4223   -1.1032 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4679    1.4414   -1.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070    0.9354   -1.5457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1571    0.9732   -3.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780    2.3612   -1.0023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5803    2.6376   -1.0056 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1673    4.0618    0.4523 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9499    3.5300    3.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    3.6778    2.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375    0.6158    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060    1.7574    1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1524    2.0898    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978   -0.2947    0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2350    0.1844    1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7452   -3.2896    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226   -2.6104    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -1.3938    3.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046   -3.3417   -0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6959   -3.4250    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707   -2.9611   -0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8394   -2.3101   -5.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4017   -3.4127   -5.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3143   -3.8585   -4.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -0.3733   -3.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -0.9155   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    1.2393   -1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738    0.2614   -1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -0.0328   -3.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427    1.4751   -3.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    1.5097   -3.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    3.0731   -1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6768    3.5195   -0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004    4.2080   -0.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  2  0
 19 17  1  0
 17 15  1  0
  8 29  1  0
  6  8  1  0
 29  6  1  0
 23  9  1  0
 25 23  1  0
  9 10  1  0
 23 22  1  0
 17 18  2  0
 19 20  1  0
 10 11  2  0
 11 12  1  0
  4  2  1  0
 12 13  1  0
 11 14  1  0
 22 52  1  1
 15 14  1  0
 23 24  1  1
 15 22  1  0
 25 26  1  0
 25 27  1  0
 29 30  1  1
  9  8  1  0
  8 39  1  1
  6  5  1  1
 29 27  1  0
 15 16  1  1
  5  4  1  0
  6  7  1  0
  2  1  1  0
 27 28  1  0
 22 21  1  0
  2  3  2  0
  5 34  1  0
  5 35  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 25 54  1  1
 27 58  1  6
  9 40  1  6
 10 41  1  0
 14 45  1  0
 14 46  1  0
 21 51  1  0
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 20 50  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 24 53  1  0
 26 55  1  0
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 26 57  1  0
 30 60  1  0
 16 47  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
 28 59  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.578   1.782   6.384  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.792   2.762   5.272  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.927   3.967   5.431  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.809   2.111   4.079  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.014   2.970   2.948  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.094   2.103   1.698  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.291   1.181   1.723  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.244   1.683   1.087  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.469   0.310   0.476  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.642  -0.423   1.117  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.961  -1.733   1.001  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.087  -2.366   1.801  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.573  -1.504   2.817  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.296  -2.739   0.058  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.442  -2.194  -1.099  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.923  -2.059  -0.702  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.433  -3.128  -2.301  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.176  -4.323  -2.251  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.691  -2.398  -3.557  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.607  -3.027  -4.891  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.999  -1.147  -3.200  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.042  -0.912  -1.711  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.506   0.422  -1.103  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.468   1.441  -1.485  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.907   0.935  -1.546  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.157   0.973  -3.062  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.178   2.361  -1.002  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.580   2.638  -1.006  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.616   2.690   0.367  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.167   4.062   0.452  0.00  0.00           O+0
HETATM   31  H   UNK     0      -1.395   1.056   6.400  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.567   2.314   7.340  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.383   1.278   6.255  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.950   3.530   3.065  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.179   3.678   2.896  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.438   0.616   0.803  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.206   1.757   1.893  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.193   0.454   2.536  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.152   2.090   1.522  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.398  -0.295   0.760  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.235   0.184   1.801  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.745  -3.290   2.279  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.923  -2.610   1.137  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.846  -1.394   3.454  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.105  -3.342  -0.381  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.696  -3.425   0.670  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.271  -2.961  -0.563  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.839  -2.310  -5.685  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.402  -3.413  -5.071  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.314  -3.858  -4.970  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.275  -0.373  -3.908  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.130  -0.916  -1.536  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.303   1.239  -1.025  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.674   0.261  -1.150  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.289  -0.033  -3.467  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.343   1.475  -3.594  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.083   1.510  -3.297  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.731   3.073  -1.710  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.677   3.519  -0.603  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.600   4.208  -0.131  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    6    4   34   35                                             
CONECT    6    8   29    5    7                                             
CONECT    7    6   36   37   38                                             
CONECT    8   29    6    9   39                                             
CONECT    9   23   10    8   40                                             
CONECT   10    9   11   41                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13   42   43                                             
CONECT   13   12   44                                                       
CONECT   14   11   15   45   46                                             
CONECT   15   17   14   22   16                                             
CONECT   16   15   47                                                       
CONECT   17   19   15   18                                                  
CONECT   18   17                                                            
CONECT   19   21   17   20                                                  
CONECT   20   19   48   49   50                                             
CONECT   21   19   22   51                                                  
CONECT   22   23   52   15   21                                             
CONECT   23    9   25   22   24                                             
CONECT   24   23   53                                                       
CONECT   25   23   26   27   54                                             
CONECT   26   25   55   56   57                                             
CONECT   27   25   29   28   58                                             
CONECT   28   27   59                                                       
CONECT   29    8    6   30   27                                             
CONECT   30   29   60                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   16                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   30                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
   -0.5783    1.7817    6.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916    2.7622    5.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274    3.9667    5.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8091    2.1111    4.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0142    2.9702    2.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943    2.1035    1.6983 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2905    1.1805    1.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2444    1.6828    1.0868 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4690    0.3095    0.4763 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6415   -0.4227    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -1.7329    1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -2.3658    1.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728   -1.5043    2.8173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2962   -2.7392    0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4418   -2.1939   -1.0991 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.6909   -2.3985   -3.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067   -3.0273   -4.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993   -1.1466   -3.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415   -0.9118   -1.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5061    0.4223   -1.1032 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4679    1.4414   -1.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070    0.9354   -1.5457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1571    0.9732   -3.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780    2.3612   -1.0023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5803    2.6376   -1.0056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6155    2.6901    0.3668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1673    4.0618    0.4523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951    1.0558    6.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5665    2.3141    7.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3827    1.2776    6.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9499    3.5300    3.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    3.6778    2.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375    0.6158    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060    1.7574    1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1929    0.4537    2.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524    2.0898    1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978   -0.2947    0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2350    0.1844    1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7452   -3.2896    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226   -2.6104    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -1.3938    3.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046   -3.3417   -0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6959   -3.4250    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707   -2.9611   -0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8394   -2.3101   -5.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4017   -3.4127   -5.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3143   -3.8585   -4.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -0.3733   -3.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1304   -0.9155   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    1.2393   -1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738    0.2614   -1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -0.0328   -3.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427    1.4751   -3.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    1.5097   -3.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    3.0731   -1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6768    3.5195   -0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004    4.2080   -0.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  2  0
 19 17  1  0
 17 15  1  0
  8 29  1  0
  6  8  1  0
 29  6  1  0
 23  9  1  0
 25 23  1  0
  9 10  1  0
 23 22  1  0
 17 18  2  0
 19 20  1  0
 10 11  2  0
 11 12  1  0
  4  2  1  0
 12 13  1  0
 11 14  1  0
 22 52  1  1
 15 14  1  0
 23 24  1  1
 15 22  1  0
 25 26  1  0
 25 27  1  0
 29 30  1  1
  9  8  1  0
  8 39  1  1
  6  5  1  1
 29 27  1  0
 15 16  1  1
  5  4  1  0
  6  7  1  0
  2  1  1  0
 27 28  1  0
 22 21  1  0
  2  3  2  0
  5 34  1  0
  5 35  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 25 54  1  1
 27 58  1  6
  9 40  1  6
 10 41  1  0
 14 45  1  0
 14 46  1  0
 21 51  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 24 53  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 30 60  1  0
 16 47  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
 28 59  1  0
M  END

View in JSmol

Synonyms

Value	Source
16-Hydroxyphorbol-16-acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₈

Average Mass

422.4740 Da

Monoisotopic Mass

422.19407 Da

IUPAC Name

[(1S,2S,6R,10S,11R,12S,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-12-yl]methyl acetate

Traditional Name

[(1S,2S,6R,10S,11R,12S,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,15-trimethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-12-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H30O8/c1-10-5-15-20(27,17(10)25)7-13(8-23)6-14-16-19(4,9-30-12(3)24)22(16,29)18(26)11(2)21(14,15)28/h5-6,11,14-16,18,23,26-29H,7-9H2,1-4H3/t11-,14+,15-,16-,18-,19-,20-,21-,22-/m1/s1

InChI Key

VTPNUNULKVERON-APOWTESASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD:CDCl₃ = 1:1, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD:CDCl₃ = 1:1, 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
Sapium insigne (ROYLE) BENTH. ex HOOK. fil.	JEOL database	Devkota, H. P., et al, Chem. Pharm. Bull. 57, 1289 (2009)

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

Tigliane diterpenoid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Cyclopropanol
Ketone
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Alcohol
Primary alcohol
Organic oxide
Hydrocarbon derivative
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	-0.05	ALOGPS
logP	-1.6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.7 m³·mol⁻¹	ChemAxon
Polarizability	43.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

44521559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Devkota HP, Basnet P, Yahara S: Diterpene esters and phenolic compounds from Sapium insigne (ROYLE) BENTH. ex HOOK. fil. Chem Pharm Bull (Tokyo). 2009 Nov;57(11):1289-91. doi: 10.1248/cpb.57.1289. [PubMed:19881284 ]
Devkota, H. P., et al. (2009). Devkota, H. P., et al, Chem. Pharm. Bull. 57, 1289 (2009). Chem. Pharm. Bull..

Showing NP-Card for 16-hydroxyphorbol-16-acetate (NP0038645)

MOL for NP0038645 (16-hydroxyphorbol-16-acetate)

3D MOL for NP0038645 (16-hydroxyphorbol-16-acetate)

3D SDF for NP0038645 (16-hydroxyphorbol-16-acetate)

3D-SDF for NP0038645 (16-hydroxyphorbol-16-acetate)

PDB for NP0038645 (16-hydroxyphorbol-16-acetate)

3D PDB for NP0038645 (16-hydroxyphorbol-16-acetate)

SMILES for NP0038645 (16-hydroxyphorbol-16-acetate)

INCHI for NP0038645 (16-hydroxyphorbol-16-acetate)

Structure for NP0038645 (16-hydroxyphorbol-16-acetate)

3D Structure for NP0038645 (16-hydroxyphorbol-16-acetate)