NP-MRD: Showing NP-Card for Stemphyloxin I (NP0007220)

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Record Information

Version

2.0

Created at

2020-12-09 04:04:17 UTC

Updated at

2021-07-15 16:57:00 UTC

NP-MRD ID

NP0007220

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stemphyloxin I

Provided By

NPAtlas

Description

Stemphyloxin I, also known as deacyl-FR 225654, belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Stemphyloxin I is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Stemphyloxin I is found in Stemphylium botryosum. Stemphyloxin I was first documented in 1982 (PMID: 16662165). Based on a literature review a small amount of articles have been published on stemphyloxin I (PMID: 17754554) (PMID: 31553484).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118383D          

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M  END


  Mrv1652306242118383D          

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   -1.4678   -2.4362   -0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401   -2.3199   -2.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717    0.0984    1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537   -2.1431    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -3.2033    2.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8904   -3.4187    1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1841   -1.9266    3.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0997   -0.9053    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567   -1.5535   -1.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.6172   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371    0.2440   -1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1778   -0.9615   -2.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3825   -1.5349   -1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1673   -2.1318    0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    0.8497    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174    1.4345   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462    2.0587    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.8586   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    2.5509   -2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491    1.1821   -2.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4505   -0.1871   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351    1.1111    2.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1924    0.5899    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598    2.2639    1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443    2.6629    1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776    4.6758    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370    5.1725   -1.4154 H   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
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 21  6  1  0  0  0  0
 20 12  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  3 33  1  1  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  5 36  1  0  0  0  0
  6 37  1  1  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  9 41  1  0  0  0  0
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 18 51  1  1  0  0  0
 19 52  1  0  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
 20 55  1  6  0  0  0
 22 56  1  0  0  0  0
 22 57  1  0  0  0  0
 22 58  1  0  0  0  0
 25 59  1  0  0  0  0
 26 60  1  0  0  0  0
 27 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007220

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C([H])=C(\[H])C(=O)[C@@]1(C([H])([H])[H])[C@@]([H])([C@]([H])(C([H])([H])O[H])C([H])([H])C([H])([H])[H])[C@](O[H])(C(=O)[C@@]2([H])C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O6/c1-6-13(11-23)17-20(4,15(24)7-8-22)16-12(2)9-19(3,26)10-14(16)18(25)21(17,5)27/h7-8,12-14,16-17,22-23,26-27H,6,9-11H2,1-5H3/b8-7-/t12-,13+,14+,16+,17-,19-,20-,21+/m1/s1

> <INCHI_KEY>
YRECHDUAXCBBOZ-HOCCXODSSA-N

> <FORMULA>
C21H34O6

> <MOLECULAR_WEIGHT>
382.497

> <EXACT_MASS>
382.235538815

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.212964264307246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4R,4aS,5R,7R,8aS)-2,7-dihydroxy-3-[(2R)-1-hydroxybutan-2-yl]-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyl-decahydronaphthalen-1-one

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.9428575096666654

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.006507374595522

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.900523289013092

> <JCHEM_PKA_STRONGEST_BASIC>
-2.59940839343665

> <JCHEM_POLAR_SURFACE_AREA>
115.06000000000002

> <JCHEM_REFRACTIVITY>
102.82339999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,4aS,5R,7R,8aS)-2,7-dihydroxy-3-[(2R)-1-hydroxybutan-2-yl]-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyl-hexahydronaphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 62  0  0  0  0  0  0  0  0999 V2000
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    2.1058    1.4402   -1.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8487    0.1116   -0.1522 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.3266    1.1558    1.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762    1.9101    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4406    2.2218   -1.1740 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0387    4.0056    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8717    0.0984    1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0997   -0.9053    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567   -1.5535   -1.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.6172   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371    0.2440   -1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1778   -0.9615   -2.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3825   -1.5349   -1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1673   -2.1318    0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    0.8497    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174    1.4345   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462    2.0587    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0837    2.5509   -2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1924    0.5899    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598    2.2639    1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443    2.6629    1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776    4.6758    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370    5.1725   -1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  1
 14 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  6
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 21  6  1  0
 20 12  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  1
  4 34  1  0
  4 35  1  0
  5 36  1  0
  6 37  1  1
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 12 42  1  1
 13 43  1  0
 13 44  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
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 17 50  1  0
 18 51  1  1
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 20 55  1  6
 22 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
 26 60  1  0
 27 61  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.546  -0.064  -1.109  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.248   0.472  -0.457  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.416  -0.697   0.085  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.064  -1.603  -1.065  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.267  -2.082  -1.617  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -0.322   1.016  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.686  -1.590   1.557  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.671  -2.642   1.940  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.135  -1.160   2.818  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.482  -2.081   0.818  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.636  -3.280   0.526  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.489  -1.093   0.428  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.512  -1.596  -0.574  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.712  -0.658  -0.367  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.649  -0.705  -1.516  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.399  -1.204   0.746  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.281   0.710   0.077  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.926   1.122  -0.433  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.106   1.440  -1.901  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.849   0.112  -0.152  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.309   0.671   0.641  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.327   1.156   1.976  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.776   1.910   0.021  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.441   2.222  -1.174  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.640   2.894   0.669  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.039   4.006   0.077  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.631   4.285  -1.240  0.00  0.00           O+0
HETATM   28  H   UNK     0      -5.336   0.746  -1.013  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.418  -0.182  -2.197  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.955  -0.921  -0.584  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.782   1.055  -1.220  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.624   0.978   0.450  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.172  -1.269   0.692  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.604  -1.042  -1.915  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.468  -2.436  -0.802  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.140  -2.320  -2.587  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.872   0.098   1.925  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.554  -2.143   2.396  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.220  -3.203   2.824  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.890  -3.419   1.220  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.184  -1.927   3.325  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.100  -0.905   1.356  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.157  -1.554  -1.607  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.800  -2.617  -0.252  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.237   0.244  -1.555  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.178  -0.962  -2.484  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.383  -1.535  -1.344  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.167  -2.132   0.906  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.306   0.850   1.177  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.017   1.435  -0.338  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.646   2.059   0.081  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.452   0.859  -2.572  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.084   2.551  -2.111  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.149   1.182  -2.266  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.451  -0.187  -1.151  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.435   1.111   2.777  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.192   0.590   2.269  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.560   2.264   1.904  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.944   2.663   1.684  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.678   4.676   0.636  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.137   5.173  -1.415  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3   31   32                                             
CONECT    3    2    4    6   33                                             
CONECT    4    3    5   34   35                                             
CONECT    5    4   36                                                       
CONECT    6    3    7   21   37                                             
CONECT    7    6    8    9   10                                             
CONECT    8    7   38   39   40                                             
CONECT    9    7   41                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20   42                                             
CONECT   13   12   14   43   44                                             
CONECT   14   13   15   16   17                                             
CONECT   15   14   45   46   47                                             
CONECT   16   14   48                                                       
CONECT   17   14   18   49   50                                             
CONECT   18   17   19   20   51                                             
CONECT   19   18   52   53   54                                             
CONECT   20   18   21   12   55                                             
CONECT   21   20   22   23    6                                             
CONECT   22   21   56   57   58                                             
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   59                                                  
CONECT   26   25   27   60                                                  
CONECT   27   26   61                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   20                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   22                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  124    0
END

RDKit          3D

61 62  0  0  0  0  0  0  0  0999 V2000
   -4.5456   -0.0639   -1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481    0.4718   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4162   -0.6972    0.0848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0638   -1.6030   -1.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2669   -2.0821   -1.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344   -0.3215    1.0160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6863   -1.5904    1.5569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6706   -2.6417    1.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1345   -1.1602    2.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824   -2.0812    0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6359   -3.2800    0.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894   -1.0926    0.4283 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5116   -1.5963   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119   -0.6582   -0.3666 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6493   -0.7054   -1.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3995   -1.2040    0.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2812    0.7096    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9258    1.1220   -0.4328 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1058    1.4402   -1.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8487    0.1116   -0.1522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3091    0.6708    0.6408 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3266    1.1558    1.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762    1.9101    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4406    2.2218   -1.1740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6395    2.8942    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    4.0056    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6311    4.2850   -1.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3356    0.7456   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4181   -0.1818   -2.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9555   -0.9206   -0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7821    1.0553   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6245    0.9776    0.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1716   -1.2690    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043   -1.0416   -1.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4678   -2.4362   -0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401   -2.3199   -2.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717    0.0984    1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537   -2.1431    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -3.2033    2.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8904   -3.4187    1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1841   -1.9266    3.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0997   -0.9053    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567   -1.5535   -1.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -2.6172   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371    0.2440   -1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1778   -0.9615   -2.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3825   -1.5349   -1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1673   -2.1318    0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    0.8497    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174    1.4345   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462    2.0587    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.8586   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837    2.5509   -2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491    1.1821   -2.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4505   -0.1871   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351    1.1111    2.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1924    0.5899    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598    2.2639    1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443    2.6629    1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6776    4.6758    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370    5.1725   -1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  1
 14 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  6
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 21  6  1  0
 20 12  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  1
  4 34  1  0
  4 35  1  0
  5 36  1  0
  6 37  1  1
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 12 42  1  1
 13 43  1  0
 13 44  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  1
 19 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  6
 22 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
 26 60  1  0
 27 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Deacyl-FR 225654	ChEBI

Chemical Formula

C₂₁H₃₄O₆

Average Mass

382.4970 Da

Monoisotopic Mass

382.23554 Da

IUPAC Name

(2S,3R,4R,4aS,5R,7R,8aS)-2,7-dihydroxy-3-[(2R)-1-hydroxybutan-2-yl]-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyl-decahydronaphthalen-1-one

Traditional Name

(2S,3R,4R,4aS,5R,7R,8aS)-2,7-dihydroxy-3-[(2R)-1-hydroxybutan-2-yl]-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyl-hexahydronaphthalen-1-one

CAS Registry Number

Not Available

SMILES

CC[C@@H](CO)[C@H]1[C@](C)(O)C(=O)[C@H]2C[C@](C)(O)C[C@@H](C)[C@@H]2[C@@]1(C)C(=O)\C=C/O

InChI Identifier

InChI=1S/C21H34O6/c1-6-13(11-23)17-20(4,15(24)7-8-22)16-12(2)9-19(3,26)10-14(16)18(25)21(17,5)27/h7-8,12-14,16-17,22-23,26-27H,6,9-11H2,1-5H3/b8-7-/t12-,13+,14+,16+,17-,19-,20-,21+/m1/s1

InChI Key

YRECHDUAXCBBOZ-HOCCXODSSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Stemphylium botryosum	NPAtlas	17754554

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Vinylogous acid
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Cyclic alcohol
Acryloyl-group
Ketone
Enol
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	1.43	ALOGPS
logP	1.94	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.9	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.82 m³·mol⁻¹	ChemAxon
Polarizability	41.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA029011

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000534

Chemspider ID

4944921

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440666

PDB ID

Not Available

ChEBI ID

145070

Good Scents ID

Not Available

References

General References

Barash I, Manulis S, Kashman Y, Springer JP, Chen MH, Clardy J, Strobel GA: Crystallization and X-ray Analysis of Stemphyloxin I, a Phytotoxin from Stemphylium botryosum. Science. 1983 Jun 3;220(4601):1065-6. doi: 10.1126/science.220.4601.1065. [PubMed:17754554 ]
Barash I, Pupkin G, Netzer D, Kashman Y: A Novel Enolic beta-Ketoaldehyde Phytotoxin Produced by Stemphylium botryosum f. sp. lycopersici : PARTIAL CHEMICAL AND BIOLOGICAL CHARACTERIZATION. Plant Physiol. 1982 Jan;69(1):23-7. doi: 10.1104/pp.69.1.23. [PubMed:16662165 ]
Li H, Hu J, Wei H, Solomon PS, Stubbs KA, Chooi YH: Biosynthesis of a Tricyclo[6.2.2.0(2,7) ]dodecane System by a Berberine Bridge Enzyme-Like Aldolase. Chemistry. 2019 Nov 27;25(66):15062-15066. doi: 10.1002/chem.201904360. Epub 2019 Oct 28. [PubMed:31553484 ]

Showing NP-Card for Stemphyloxin I (NP0007220)

MOL for NP0007220 (Stemphyloxin I)

3D MOL for NP0007220 (Stemphyloxin I)

3D SDF for NP0007220 (Stemphyloxin I)

3D-SDF for NP0007220 (Stemphyloxin I)

PDB for NP0007220 (Stemphyloxin I)

3D PDB for NP0007220 (Stemphyloxin I)

SMILES for NP0007220 (Stemphyloxin I)

INCHI for NP0007220 (Stemphyloxin I)

Structure for NP0007220 (Stemphyloxin I)

3D Structure for NP0007220 (Stemphyloxin I)