NP-MRD: Showing NP-Card for trichodermanone A (NP0025217)

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Record Information

Version

2.0

Created at

2021-06-19 17:24:00 UTC

Updated at

2021-06-29 23:50:00 UTC

NP-MRD ID

NP0025217

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trichodermanone A

Provided By

JEOL Database JEOL Logo

Description

trichodermanone A is found in Trichoderma Species. trichodermanone A was first documented in 2007 (Neumann, K., et al.). Based on a literature review very few articles have been published on (1R,2R,5S,7R,8R,10S,11Z)-2,10-dihydroxy-11-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-5-(hydroxymethyl)-5-methoxy-8,10-dimethyl-4-oxatricyclo[6.2.2.0²,⁷]Dodecane-9,12-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119243D          

 57 59  0  0  0  0            999 V2000
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   -3.5028   -3.1683    6.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0468   -2.6130    5.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3640   -0.1891    4.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    0.0675    5.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635    0.3940    2.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    1.3733    2.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9267    1.5198    3.9659 O   0  0  0  0  0  0  0  0  0  0  0  0
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 23 22  1  0  0  0  0
  5  4  2  0  0  0  0
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  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 18 15  1  0  0  0  0
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M  END

     RDKit          3D

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    0.0635    0.3940    2.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    1.3733    2.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192119243D          

 57 59  0  0  0  0            999 V2000
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   -3.5028   -3.1683    6.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5194   -2.8589    4.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666   -1.4514    6.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669   -1.3827    3.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0306    0.6055    5.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    3.8807    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616    2.9331    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692    4.0001    2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    2.0363    2.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982    1.0260    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    2.7428    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    2.3834   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340   -0.6189    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -1.6325    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033   -1.6369   -0.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056   -0.0523   -1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0360    0.1932   -1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -1.0553   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4589   -2.1074   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633    0.3383   -4.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9294   -0.5329   -3.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9071    1.1394   -4.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105    1.7927   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    0.3238    0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958    1.7568   -0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0  0  0  0
  5  4  2  0  0  0  0
 22 21  1  0  0  0  0
  4  3  1  0  0  0  0
 21 19  1  0  0  0  0
  3  2  2  0  0  0  0
 29 11  1  0  0  0  0
  2  1  1  0  0  0  0
 19 18  1  0  0  0  0
  6  7  1  0  0  0  0
 18  8  1  0  0  0  0
 11 12  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 15 16  1  0  0  0  0
 29 19  1  0  0  0  0
 15 17  1  6  0  0  0
 11 13  1  0  0  0  0
 19 20  1  1  0  0  0
 23 24  1  0  0  0  0
 18 15  1  0  0  0  0
 23 26  1  6  0  0  0
 13 15  1  0  0  0  0
 24 25  1  0  0  0  0
 28 23  1  0  0  0  0
 26 27  1  0  0  0  0
  8  6  2  0  0  0  0
 29 57  1  6  0  0  0
 28 29  1  0  0  0  0
 13 14  2  0  0  0  0
  6  5  1  0  0  0  0
 18 45  1  1  0  0  0
 28 55  1  0  0  0  0
 28 56  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
  5 36  1  0  0  0  0
  4 35  1  0  0  0  0
  3 34  1  0  0  0  0
  2 33  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  7 37  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 16 43  1  0  0  0  0
 17 44  1  0  0  0  0
 20 46  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 25 51  1  0  0  0  0
 27 52  1  0  0  0  0
 27 53  1  0  0  0  0
 27 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C(\C(\[H])=C(/[H])\C(\[H])=C(/[H])C([H])([H])[H])=C1/C(=O)[C@@]2(C(=O)[C@](O[H])(C([H])([H])[H])[C@@]1([H])[C@@]1(O[H])C([H])([H])O[C@](OC([H])([H])[H])(C([H])([H])O[H])C([H])([H])[C@]21[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O8/c1-5-6-7-8-12(23)14-15-19(3,26)17(25)18(2,16(14)24)13-9-20(10-22,28-4)29-11-21(13,15)27/h5-8,13,15,22-23,26-27H,9-11H2,1-4H3/b6-5+,8-7+,14-12-/t13-,15+,18-,19+,20+,21-/m1/s1

> <INCHI_KEY>
YNIAATPACSDVQQ-WILUIMLGSA-N

> <FORMULA>
C21H28O8

> <MOLECULAR_WEIGHT>
408.447

> <EXACT_MASS>
408.178417862

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.89798642791588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,7R,8R,10S,11Z)-2,10-dihydroxy-11-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-5-(hydroxymethyl)-5-methoxy-8,10-dimethyl-4-oxatricyclo[6.2.2.0^{2,7}]dodecane-9,12-dione

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
0.6218628669999992

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.761570094371955

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.301097812439762

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4142792175758165

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
107.00710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,7R,8R,10S,11Z)-2,10-dihydroxy-11-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-5-(hydroxymethyl)-5-methoxy-8,10-dimethyl-4-oxatricyclo[6.2.2.0^{2,7}]dodecane-9,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -4.6466   -4.1279    6.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5028   -3.1683    6.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0468   -2.6130    5.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9360   -1.6871    5.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755   -1.1234    4.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3640   -0.1891    4.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    0.0675    5.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635    0.3940    2.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    1.3733    2.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9267    1.5198    3.9659 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    2.1642    1.6712 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3607    3.3046    1.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0610    2.6858    1.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3419    3.8729    1.1990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    1.5578    1.1099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3863    1.8538    1.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4483    1.5020   -0.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    0.2188    1.5233 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8288   -0.0891    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6227   -1.0374    1.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6777   -0.7064   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0106   -1.0766   -1.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9364    0.0339   -1.3098 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3356   -0.5733   -1.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664   -1.5970   -2.6132 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    0.9439   -2.3249 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4534    0.4260   -3.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0434    0.8762    0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6295    1.2211    0.4692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4404   -3.7250    7.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0700   -4.3256    5.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -5.0797    6.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354   -2.9289    7.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -2.8589    4.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666   -1.4514    6.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669   -1.3827    3.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0306    0.6055    5.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    3.8807    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616    2.9331    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692    4.0001    2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    2.0363    2.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982    1.0260    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    2.7428    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    2.3834   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340   -0.6189    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -1.6325    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033   -1.6369   -0.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056   -0.0523   -1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0360    0.1932   -1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -1.0553   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4589   -2.1074   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633    0.3383   -4.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9294   -0.5329   -3.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9071    1.1394   -4.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105    1.7927   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    0.3238    0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958    1.7568   -0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
  5  4  2  0
 22 21  1  0
  4  3  1  0
 21 19  1  0
  3  2  2  0
 29 11  1  0
  2  1  1  0
 19 18  1  0
  6  7  1  0
 18  8  1  0
 11 12  1  1
  8  9  1  0
  9 10  2  0
  9 11  1  0
 15 16  1  0
 29 19  1  0
 15 17  1  6
 11 13  1  0
 19 20  1  1
 23 24  1  0
 18 15  1  0
 23 26  1  6
 13 15  1  0
 24 25  1  0
 28 23  1  0
 26 27  1  0
  8  6  2  0
 29 57  1  6
 28 29  1  0
 13 14  2  0
  6  5  1  0
 18 45  1  1
 28 55  1  0
 28 56  1  0
 21 47  1  0
 21 48  1  0
  5 36  1  0
  4 35  1  0
  3 34  1  0
  2 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 20 46  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.647  -4.128   6.512  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.503  -3.168   6.457  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.047  -2.613   5.324  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.936  -1.687   5.299  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.476  -1.123   4.170  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.364  -0.189   4.099  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.221   0.068   5.327  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.064   0.394   2.964  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.217   1.373   2.976  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.927   1.520   3.966  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.361   2.164   1.671  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.361   3.305   1.795  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.061   2.686   1.346  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.342   3.873   1.199  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.110   1.558   1.110  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.386   1.854   1.899  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.448   1.502  -0.273  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.438   0.219   1.523  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.829  -0.089   0.661  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.623  -1.037   1.420  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.678  -0.706  -0.731  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.011  -1.077  -1.174  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.936   0.034  -1.310  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.336  -0.573  -1.612  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.266  -1.597  -2.613  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.490   0.944  -2.325  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.453   0.426  -3.646  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.043   0.876   0.004  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.630   1.221   0.469  0.00  0.00           C+0
HETATM   30  H   UNK     0      -5.440  -3.725   7.148  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.070  -4.326   5.522  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.314  -5.080   6.937  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.035  -2.929   7.410  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.519  -2.859   4.376  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.467  -1.451   6.253  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.967  -1.383   3.237  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.031   0.606   5.184  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.427   3.881   0.865  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.362   2.933   2.040  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.069   4.000   2.591  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.191   2.036   2.960  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.098   1.026   1.808  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.891   2.743   1.502  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.798   2.383  -0.516  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.134  -0.619   1.422  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.072  -1.633   0.786  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.103  -1.637  -0.677  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.206  -0.052  -1.469  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.036   0.193  -1.957  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.745  -1.055  -0.718  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.459  -2.107  -2.406  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.463   0.338  -4.055  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.929  -0.533  -3.690  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.907   1.139  -4.270  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.611   1.793  -0.196  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.573   0.324   0.789  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.196   1.757  -0.391  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1   33                                                  
CONECT    3    4    2   34                                                  
CONECT    4    5    3   35                                                  
CONECT    5    4    6   36                                                  
CONECT    6    7    8    5                                                  
CONECT    7    6   37                                                       
CONECT    8   18    9    6                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11   29   12    9   13                                             
CONECT   12   11   38   39   40                                             
CONECT   13   11   15   14                                                  
CONECT   14   13                                                            
CONECT   15   16   17   18   13                                             
CONECT   16   15   41   42   43                                             
CONECT   17   15   44                                                       
CONECT   18   19    8   15   45                                             
CONECT   19   21   18   29   20                                             
CONECT   20   19   46                                                       
CONECT   21   22   19   47   48                                             
CONECT   22   23   21                                                       
CONECT   23   22   24   26   28                                             
CONECT   24   23   25   49   50                                             
CONECT   25   24   51                                                       
CONECT   26   23   27                                                       
CONECT   27   26   52   53   54                                             
CONECT   28   23   29   55   56                                             
CONECT   29   11   19   57   28                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   27                                                            
CONECT   53   27                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
   -4.6466   -4.1279    6.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5028   -3.1683    6.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0468   -2.6130    5.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9360   -1.6871    5.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755   -1.1234    4.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3640   -0.1891    4.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    0.0675    5.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635    0.3940    2.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    1.3733    2.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9267    1.5198    3.9659 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    2.1642    1.6712 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3607    3.3046    1.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0610    2.6858    1.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3419    3.8729    1.1990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    1.5578    1.1099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3863    1.8538    1.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4483    1.5020   -0.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    0.2188    1.5233 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8288   -0.0891    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6227   -1.0374    1.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6777   -0.7064   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0106   -1.0766   -1.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9364    0.0339   -1.3098 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3356   -0.5733   -1.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664   -1.5970   -2.6132 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    0.9439   -2.3249 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4534    0.4260   -3.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0434    0.8762    0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6295    1.2211    0.4692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4404   -3.7250    7.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0700   -4.3256    5.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -5.0797    6.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354   -2.9289    7.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -2.8589    4.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666   -1.4514    6.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669   -1.3827    3.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0306    0.6055    5.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    3.8807    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616    2.9331    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692    4.0001    2.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    2.0363    2.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982    1.0260    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    2.7428    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    2.3834   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340   -0.6189    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -1.6325    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033   -1.6369   -0.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056   -0.0523   -1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0360    0.1932   -1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -1.0553   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4589   -2.1074   -2.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633    0.3383   -4.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9294   -0.5329   -3.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9071    1.1394   -4.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105    1.7927   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    0.3238    0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958    1.7568   -0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
  5  4  2  0
 22 21  1  0
  4  3  1  0
 21 19  1  0
  3  2  2  0
 29 11  1  0
  2  1  1  0
 19 18  1  0
  6  7  1  0
 18  8  1  0
 11 12  1  1
  8  9  1  0
  9 10  2  0
  9 11  1  0
 15 16  1  0
 29 19  1  0
 15 17  1  6
 11 13  1  0
 19 20  1  1
 23 24  1  0
 18 15  1  0
 23 26  1  6
 13 15  1  0
 24 25  1  0
 28 23  1  0
 26 27  1  0
  8  6  2  0
 29 57  1  6
 28 29  1  0
 13 14  2  0
  6  5  1  0
 18 45  1  1
 28 55  1  0
 28 56  1  0
 21 47  1  0
 21 48  1  0
  5 36  1  0
  4 35  1  0
  3 34  1  0
  2 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 20 46  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₈

Average Mass

408.4470 Da

Monoisotopic Mass

408.17842 Da

IUPAC Name

(1R,2R,5S,7R,8R,10S,11Z)-2,10-dihydroxy-11-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-5-(hydroxymethyl)-5-methoxy-8,10-dimethyl-4-oxatricyclo[6.2.2.0^{2,7}]dodecane-9,12-dione

Traditional Name

(1R,2R,5S,7R,8R,10S,11Z)-2,10-dihydroxy-11-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-5-(hydroxymethyl)-5-methoxy-8,10-dimethyl-4-oxatricyclo[6.2.2.0^{2,7}]dodecane-9,12-dione

CAS Registry Number

Not Available

SMILES

[H]O\C(\C(\[H])=C(/[H])\C(\[H])=C(/[H])C([H])([H])[H])=C1/C(=O)[C@@]2(C(=O)[C@](O[H])(C([H])([H])[H])[C@@]1([H])[C@@]1(O[H])C([H])([H])O[C@](OC([H])([H])[H])(C([H])([H])O[H])C([H])([H])[C@]21[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H28O8/c1-5-6-7-8-12(23)14-15-19(3,26)17(25)18(2,16(14)24)13-9-20(10-22,28-4)29-11-21(13,15)27/h5-8,13,15,22-23,26-27H,9-11H2,1-4H3/b6-5+,8-7+,14-12-/t13-,15+,18-,19+,20+,21-/m1/s1

InChI Key

YNIAATPACSDVQQ-WILUIMLGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Trichoderma Species	JEOL database	Neumann, K., et al, Eur. J. Org. Chem. 2007, 2268.

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	1.02	ALOGPS
logP	0.62	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.01 m³·mol⁻¹	ChemAxon
Polarizability	41.9 Å³	ChemAxon
Number of Rings	3	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17625174

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16720811

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Neumann, K., et al. (2007). Neumann, K., et al, Eur. J. Org. Chem. 2007, 2268.. Eur. J. Org. Chem..

Showing NP-Card for trichodermanone A (NP0025217)

MOL for NP0025217 (trichodermanone A)

3D MOL for NP0025217 (trichodermanone A)

3D SDF for NP0025217 (trichodermanone A)

3D-SDF for NP0025217 (trichodermanone A)

PDB for NP0025217 (trichodermanone A)

3D PDB for NP0025217 (trichodermanone A)

SMILES for NP0025217 (trichodermanone A)

INCHI for NP0025217 (trichodermanone A)

Structure for NP0025217 (trichodermanone A)

3D Structure for NP0025217 (trichodermanone A)