NP-MRD: Showing NP-Card for Terpendole E (NP0022263)

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Record Information

Version

2.0

Created at

2021-01-06 07:28:27 UTC

Updated at

2021-07-15 17:38:34 UTC

NP-MRD ID

NP0022263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Terpendole E

Provided By

NPAtlas

Description

TERPENDOLE E is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Terpendole E is found in Albophoma yamanashiensis, Chaunopycnis alba, Neotyphodium coenophialum e822, Neotyphodium coenophialum Tf28, Neotyphodium festucae Frc7, Neotyphodium funkii e4096, Neotyphodium lolii AR1, Neotyphodium lolii Lp14, Neotyphodium lolii Lp19, Neotyphodium siegelii e915, Neotyphodium tembladerae e1169, Neotyphodium tembladerae e4055 and Tolypocladium cylindrosporum. Terpendole E was first documented in 2016 (PMID: 27865702). Based on a literature review a small amount of articles have been published on TERPENDOLE E (PMID: 28674820) (PMID: 28571312) (PMID: 28062800).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105223D          

 71 76  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
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 11 48  1  6
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 15 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  6
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  1
 20 62  1  0
 20 63  1  0
 23 64  1  0
 25 65  1  0
 26 66  1  0
 27 67  1  0
 28 68  1  0
 31 69  1  0
 31 70  1  0
 31 71  1  0
M  END


  Mrv1652306242105223D          

 71 76  0  0  0  0            999 V2000
   -5.8133   -0.9922    0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6231    0.3050   -0.2702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8723    1.4263    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4961    0.3676   -1.3292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1696    0.4364   -0.6892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8258   -0.6491   -1.6809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3536   -0.8021   -1.8617 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7937    0.1155   -2.7398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -0.7438   -0.5303 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.0657    0.5497    0.1372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3183    0.8340    1.3890 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1587    0.9095    1.1269 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7259   -0.1964    0.3210 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9495   -1.3749    1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2483    0.2536    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581    0.7361    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049    1.4977    1.6004 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316    1.5112    1.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292    2.1351    2.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7974    1.9889    2.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4273    1.2105    1.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6396    0.5922    0.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2497    0.7377    0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0112    0.2152   -0.3257 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8511    1.1314   -1.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4065    0.3571    0.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0071   -2.6812   -1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  6  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
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 14 16  1  0  0  0  0
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 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
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 22 30  1  0  0  0  0
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 11 32  1  0  0  0  0
 32  5  1  0  0  0  0
 16  9  1  0  0  0  0
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 29 21  1  0  0  0  0
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  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  4 39  1  0  0  0  0
  5 40  1  6  0  0  0
  6 41  1  0  0  0  0
  6 42  1  0  0  0  0
  7 43  1  6  0  0  0
  8 44  1  0  0  0  0
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 31 69  1  0  0  0  0
 31 70  1  0  0  0  0
 31 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@]([H])(O[C@@]2([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@@]4([H])C([H])([H])C5=C(N([H])C6=C([H])C([H])=C([H])C([H])=C56)[C@]34C([H])([H])[H])[C@]12C([H])([H])[H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO3/c1-25(2,31)23-15-21(30)27(4)20-11-10-16-14-18-17-8-6-7-9-19(17)29-24(18)28(16,5)26(20,3)13-12-22(27)32-23/h6-9,16,20-23,29-31H,10-15H2,1-5H3/t16-,20+,21+,22-,23-,26-,27+,28+/m0/s1

> <INCHI_KEY>
SVYIMXYKHRBHSG-KYYKPQATSA-N

> <FORMULA>
C28H39NO3

> <MOLECULAR_WEIGHT>
437.624

> <EXACT_MASS>
437.29299412

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.03837821139396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,7S,9R,10R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-16(24),17,19,21-tetraen-9-ol

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
4.332317066666665

> <ALOGPS_LOGS>
-5.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.745432727401251

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.112975691108733

> <JCHEM_PKA_STRONGEST_BASIC>
-3.002719029207398

> <JCHEM_POLAR_SURFACE_AREA>
65.48

> <JCHEM_REFRACTIVITY>
126.4986

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7S,9R,10R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-16(24),17,19,21-tetraen-9-ol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
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   -4.1696    0.4364   -0.6892 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.0071   -2.6812   -1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1256   -1.2602   -2.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -2.7614   -2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619   -1.8135    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0508   -0.0114   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7190   -1.4740   -1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6081    2.0327    2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9032    2.7356    3.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3937    2.4957    3.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4978    1.1212    1.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1136   -0.0229    0.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1353    1.9441   -1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360    0.6558   -2.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8439    1.6527   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  6
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 22 30  1  0
 30 31  1  6
 11 32  1  0
 32  5  1  0
 16  9  1  0
 30 19  1  0
 30 14  1  0
 29 21  1  0
 29 24  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  5 40  1  6
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
 10 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  6
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 12 50  1  0
 13 51  1  0
 13 52  1  0
 15 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  6
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 19 61  1  1
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 20 63  1  0
 23 64  1  0
 25 65  1  0
 26 66  1  0
 27 67  1  0
 28 68  1  0
 31 69  1  0
 31 70  1  0
 31 71  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      -5.813  -0.992   0.492  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.623   0.305  -0.270  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.872   1.426   0.747  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.496   0.368  -1.329  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.170   0.436  -0.689  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.826  -0.649  -1.681  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.354  -0.802  -1.862  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.794   0.116  -2.740  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.592  -0.744  -0.530  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.969  -1.903   0.293  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.066   0.550   0.137  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.318   0.834   1.389  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.159   0.910   1.127  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.726  -0.196   0.321  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.950  -1.375   1.233  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.164  -0.564  -0.864  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.377  -1.671  -1.694  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.846  -1.674  -1.906  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.636  -1.109  -0.797  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.008  -0.616  -1.151  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.248   0.254   0.065  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.058   0.736   0.537  0.00  0.00           C+0
HETATM   23  N   UNK     0       3.305   1.498   1.600  0.00  0.00           N+0
HETATM   24  C   UNK     0       4.632   1.511   1.818  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.429   2.135   2.780  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.797   1.989   2.789  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.427   1.210   1.834  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.640   0.592   0.881  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.250   0.738   0.868  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.011   0.215  -0.326  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.851   1.131  -1.505  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.406   0.357   0.464  0.00  0.00           O+0
HETATM   33  H   UNK     0      -6.680  -0.945   1.192  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.832  -1.874  -0.148  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.908  -1.092   1.160  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.159   1.229   1.583  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.598   2.390   0.306  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.910   1.378   1.134  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.956  -0.526  -1.430  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.024   1.410  -1.200  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.300  -1.611  -1.470  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.247  -0.307  -2.669  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.144  -1.811  -2.283  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.417   0.871  -2.820  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.339  -2.804   0.186  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.001  -2.238  -0.027  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.108  -1.637   1.375  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.924   1.386  -0.560  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.523   0.125   2.217  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.639   1.830   1.758  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.447   1.924   0.785  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.626   0.810   2.159  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.907  -1.203   1.766  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.945  -2.349   0.753  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.176  -1.377   2.058  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.128   0.364  -1.515  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.100  -1.573  -2.716  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.007  -2.681  -1.344  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.126  -1.260  -2.921  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.156  -2.761  -2.005  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.762  -1.813   0.031  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.051  -0.011  -2.059  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.719  -1.474  -1.157  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.608   2.033   2.208  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.903   2.736   3.511  0.00  0.00           H+0
HETATM   66  H   UNK     0       7.394   2.496   3.562  0.00  0.00           H+0
HETATM   67  H   UNK     0       8.498   1.121   1.875  0.00  0.00           H+0
HETATM   68  H   UNK     0       7.114  -0.023   0.123  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.135   1.944  -1.338  0.00  0.00           H+0
HETATM   70  H   UNK     0       1.636   0.656  -2.457  0.00  0.00           H+0
HETATM   71  H   UNK     0       2.844   1.653  -1.654  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3    4    5                                             
CONECT    3    2   36   37   38                                             
CONECT    4    2   39                                                       
CONECT    5    2    6   32   40                                             
CONECT    6    5    7   41   42                                             
CONECT    7    6    8    9   43                                             
CONECT    8    7   44                                                       
CONECT    9    7   10   11   16                                             
CONECT   10    9   45   46   47                                             
CONECT   11    9   12   32   48                                             
CONECT   12   11   13   49   50                                             
CONECT   13   12   14   51   52                                             
CONECT   14   13   15   16   30                                             
CONECT   15   14   53   54   55                                             
CONECT   16   14   17    9   56                                             
CONECT   17   16   18   57   58                                             
CONECT   18   17   19   59   60                                             
CONECT   19   18   20   30   61                                             
CONECT   20   19   21   62   63                                             
CONECT   21   20   22   29                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   24   64                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   65                                                  
CONECT   26   25   27   66                                                  
CONECT   27   26   28   67                                                  
CONECT   28   27   29   68                                                  
CONECT   29   28   21   24                                                  
CONECT   30   22   31   19   14                                             
CONECT   31   30   69   70   71                                             
CONECT   32   11    5                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    8                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   15                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   17                                                            
CONECT   58   17                                                            
CONECT   59   18                                                            
CONECT   60   18                                                            
CONECT   61   19                                                            
CONECT   62   20                                                            
CONECT   63   20                                                            
CONECT   64   23                                                            
CONECT   65   25                                                            
CONECT   66   26                                                            
CONECT   67   27                                                            
CONECT   68   28                                                            
CONECT   69   31                                                            
CONECT   70   31                                                            
CONECT   71   31                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  152    0
END

RDKit          3D

71 76  0  0  0  0  0  0  0  0999 V2000
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   -5.6231    0.3050   -0.2702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8723    1.4263    0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4961    0.3676   -1.3292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1696    0.4364   -0.6892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8258   -0.6491   -1.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3536   -0.8021   -1.8617 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7937    0.1155   -2.7398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -0.7438   -0.5303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9693   -1.9026    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0657    0.5497    0.1372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3183    0.8340    1.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587    0.9095    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -0.1964    0.3210 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9495   -1.3749    1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8464   -1.6744   -1.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0581    0.7361    0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049    1.4977    1.6004 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7974    1.9889    2.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6396    0.5922    0.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2497    0.7377    0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0112    0.2152   -0.3257 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.4065    0.3571    0.4638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6798   -0.9454    1.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8320   -1.8737   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5985    2.3900    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9096    1.3777    1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9563   -0.5256   -1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0237    1.4103   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003   -1.6111   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2470   -0.3066   -2.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442   -1.8112   -2.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    0.8712   -2.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395   -2.8044    0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013   -2.2379   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078   -1.6365    1.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241    1.3860   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228    0.1251    2.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6393    1.8303    1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1282    0.3641   -1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996   -1.5729   -2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071   -2.6812   -1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1561   -2.7614   -2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619   -1.8135    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0508   -0.0114   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7190   -1.4740   -1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6081    2.0327    2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9032    2.7356    3.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3937    2.4957    3.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4978    1.1212    1.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1136   -0.0229    0.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1353    1.9441   -1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360    0.6558   -2.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8439    1.6527   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  6
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
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 16 17  1  0
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 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 22 30  1  0
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 11 32  1  0
 32  5  1  0
 16  9  1  0
 30 19  1  0
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 29 21  1  0
 29 24  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  5 40  1  6
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
 10 45  1  0
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 10 47  1  0
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 31 71  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO₃

Average Mass

437.6240 Da

Monoisotopic Mass

437.29299 Da

IUPAC Name

(1S,2S,5S,7S,9R,10R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-16(24),17,19,21-tetraen-9-ol

Traditional Name

(1S,2S,5S,7S,9R,10R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-16(24),17,19,21-tetraen-9-ol

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1C[C@@H](O)[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2CC4=C(NC5=CC=CC=C45)[C@]32C)O1

InChI Identifier

InChI=1S/C28H39NO3/c1-25(2,31)23-15-21(30)27(4)20-11-10-16-14-18-17-8-6-7-9-19(17)29-24(18)28(16,5)26(20,3)13-12-22(27)32-23/h6-9,16,20-23,29-31H,10-15H2,1-5H3/t16-,20+,21+,22-,23-,26-,27+,28+/m0/s1

InChI Key

SVYIMXYKHRBHSG-KYYKPQATSA-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
Albophoma yamanashiensis	NPAtlas	7592023
Chaunopycnis alba	-	KNApSAcK
Neotyphodium coenophialum e822	-	KNApSAcK
Neotyphodium coenophialum Tf28	-	KNApSAcK
Neotyphodium festucae Frc7	-	KNApSAcK
Neotyphodium funkii e4096	-	KNApSAcK
Neotyphodium lolii AR1	-	KNApSAcK
Neotyphodium lolii Lp14	-	KNApSAcK
Neotyphodium lolii Lp19	-	KNApSAcK
Neotyphodium siegelii e915	-	KNApSAcK
Neotyphodium tembladerae e1169	-	KNApSAcK
Neotyphodium tembladerae e4055	-	KNApSAcK
Tolypocladium cylindrosporum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Epichloe festucae Fg1	KNApSAcK Database	22123792
Epichloe festucae Fl1	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	5.46	ALOGPS
logP	4.33	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	14.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.48 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	126.5 m³·mol⁻¹	ChemAxon
Polarizability	52.04 Å³	ChemAxon
Number of Rings	6	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

NPAtlas ID

NPA016267

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016560

Chemspider ID

8270167

KEGG Compound ID

C20536

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10094631

PDB ID

Not Available

ChEBI ID

138863

Good Scents ID

Not Available

References

General References

Bauer JI, Gross M, Cramer B, Wegner S, Hausmann H, Hamscher G, Usleber E: Detection of the tremorgenic mycotoxin paxilline and its desoxy analog in ergot of rye and barley: a new class of mycotoxins added to an old problem. Anal Bioanal Chem. 2017 Aug;409(21):5101-5112. doi: 10.1007/s00216-017-0455-y. Epub 2017 Jul 4. [PubMed:28674820 ]
Lee ST, Gardner DR, Cook D: Identification of Indole Diterpenes in Ipomoea asarifolia and Ipomoea muelleri, Plants Tremorgenic to Livestock. J Agric Food Chem. 2017 Jul 5;65(26):5266-5277. doi: 10.1021/acs.jafc.7b01834. Epub 2017 Jun 20. [PubMed:28571312 ]
Sheff JG, Farshidfar F, Bathe OF, Kopciuk K, Gentile F, Tuszynski J, Barakat K, Schriemer DC: Novel Allosteric Pathway of Eg5 Regulation Identified through Multivariate Statistical Analysis of Hydrogen-Exchange Mass Spectrometry (HX-MS) Ligand Screening Data. Mol Cell Proteomics. 2017 Mar;16(3):428-437. doi: 10.1074/mcp.M116.064246. Epub 2017 Jan 5. [PubMed:28062800 ]
Motoyama T, Osada H: Biosynthetic approaches to creating bioactive fungal metabolites: Pathway engineering and activation of secondary metabolism. Bioorg Med Chem Lett. 2016 Dec 15;26(24):5843-5850. doi: 10.1016/j.bmcl.2016.11.013. Epub 2016 Nov 9. [PubMed:27865702 ]

Showing NP-Card for Terpendole E (NP0022263)

MOL for NP0022263 (Terpendole E)

3D MOL for NP0022263 (Terpendole E)

3D SDF for NP0022263 (Terpendole E)

3D-SDF for NP0022263 (Terpendole E)

PDB for NP0022263 (Terpendole E)

3D PDB for NP0022263 (Terpendole E)

SMILES for NP0022263 (Terpendole E)

INCHI for NP0022263 (Terpendole E)

Structure for NP0022263 (Terpendole E)

3D Structure for NP0022263 (Terpendole E)