NP-MRD: Showing NP-Card for 12beta-hydroxychaetoviridin C (NP0035956)

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Record Information

Version

2.0

Created at

2021-06-20 19:15:31 UTC

Updated at

2021-06-30 00:07:20 UTC

NP-MRD ID

NP0035956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12beta-hydroxychaetoviridin C

Provided By

JEOL Database JEOL Logo

Description

12Beta-hydroxychaetoviridin C belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 12beta-hydroxychaetoviridin C is found in Chaetomium globosum. 12beta-hydroxychaetoviridin C was first documented in 2011 (PMID: 21548578). Based on a literature review very few articles have been published on 12beta-hydroxychaetoviridin C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121153D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202121153D          

 58 60  0  0  0  0            999 V2000
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   -2.9607    0.0293    0.2882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2072    4.9827    3.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564    5.4791    1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275    5.5537    2.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612    2.9761    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    4.0743    0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0110    3.2725    2.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7518    3.8043    4.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6339    2.4544    4.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    2.1391    4.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5689    1.9908    0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386   -2.5129   -0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4155   -1.8788   -0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0579    1.4471   -3.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7014   -0.1492   -3.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750    1.3601   -5.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    0.5580   -5.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -0.3922   -5.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9410    1.9317   -3.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1164    3.4068   -4.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838    4.1380   -3.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3872    3.4714   -2.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797    1.9303   -1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874    1.6117   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    0.3060   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  2  0  0  0  0
  6  4  1  0  0  0  0
 29 28  1  0  0  0  0
  4  2  1  0  0  0  0
 28 20  1  0  0  0  0
  2  1  1  0  0  0  0
 20 19  2  0  0  0  0
  6  7  2  0  0  0  0
 31 12  1  0  0  0  0
  4  5  1  0  0  0  0
  2  3  1  0  0  0  0
 14 12  1  0  0  0  0
 20 21  1  0  0  0  0
 14 16  1  0  0  0  0
 21 22  2  0  0  0  0
 31 30  1  0  0  0  0
 22 23  1  0  0  0  0
 18 16  2  0  0  0  0
 23 25  1  0  0  0  0
 12 11  1  0  0  0  0
 25 26  1  0  0  0  0
 11  9  1  0  0  0  0
 16 17  1  0  0  0  0
  9  8  1  0  0  0  0
 14 15  2  0  0  0  0
  8 31  1  0  0  0  0
 23 24  1  0  0  0  0
 18 30  1  0  0  0  0
 12 13  1  6  0  0  0
  9 10  2  0  0  0  0
  8 41  1  6  0  0  0
 18 19  1  0  0  0  0
 31 58  1  6  0  0  0
  8  6  1  0  0  0  0
 25 27  1  0  0  0  0
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  4 37  1  1  0  0  0
  2 35  1  6  0  0  0
  1 32  1  0  0  0  0
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  1 34  1  0  0  0  0
  5 38  1  0  0  0  0
  5 39  1  0  0  0  0
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  3 36  1  0  0  0  0
 21 46  1  0  0  0  0
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 25 52  1  6  0  0  0
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 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 27 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C([H])([H])[H])[C@@]([H])(C(\[H])=C(/[H])C1=C([H])C2=C(Cl)C(=O)[C@]3(OC(=O)[C@@]([H])(C(=O)[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[H])[C@@]3([H])C2=C([H])O1)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H27ClO7/c1-10(12(3)25)6-7-14-8-15-16(9-30-14)18-17(20(27)11(2)13(4)26)22(29)31-23(18,5)21(28)19(15)24/h6-13,17-18,25-26H,1-5H3/b7-6+/t10-,11+,12-,13+,17-,18-,23+/m1/s1

> <INCHI_KEY>
MEPQPODJTXSHEP-HETSEVKPSA-N

> <FORMULA>
C23H27ClO7

> <MOLECULAR_WEIGHT>
450.91

> <EXACT_MASS>
450.1445309

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.79732888655549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6aS,9R,9aS)-5-chloro-9-[(2S,3S)-3-hydroxy-2-methylbutanoyl]-3-[(1E,3R,4R)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
1.9005210573333324

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.169394868939445

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.735102937874395

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3680110562855572

> <JCHEM_POLAR_SURFACE_AREA>
110.13

> <JCHEM_REFRACTIVITY>
117.84630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aS,9R,9aS)-5-chloro-9-[(2S,3S)-3-hydroxy-2-methylbutanoyl]-3-[(1E,3R,4R)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9H,9aH-furo[2,3-h]isochromene-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
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   -4.0932   -2.1905   -0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483   -2.0452    1.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7436   -2.6944    2.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554   -2.0558    1.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -3.3209    1.7008 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6607   -1.1381    0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -1.1379   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -0.2181   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3584   -0.1705   -1.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570    0.7039   -2.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514    0.7198   -3.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0581    0.5578   -4.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647    1.9791   -3.0426 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3191    3.3167   -3.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359    1.9603   -1.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1458    0.7583   -1.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1179    0.7904   -1.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677   -0.0697   -0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9607    0.0293    0.2882 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.6339    2.4544    4.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    2.1391    4.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5689    1.9908    0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386   -2.5129   -0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5189   -3.0885    0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9127   -1.7048   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4155   -1.8788   -0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704   -0.9126   -1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0579    1.4471   -3.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7014   -0.1492   -3.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750    1.3601   -5.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    0.5580   -5.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -0.3922   -5.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9410    1.9317   -3.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1164    3.4068   -4.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838    4.1380   -3.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3872    3.4714   -2.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797    1.9303   -1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874    1.6117   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    0.3060   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  2  0
  6  4  1  0
 29 28  1  0
  4  2  1  0
 28 20  1  0
  2  1  1  0
 20 19  2  0
  6  7  2  0
 31 12  1  0
  4  5  1  0
  2  3  1  0
 14 12  1  0
 20 21  1  0
 14 16  1  0
 21 22  2  0
 31 30  1  0
 22 23  1  0
 18 16  2  0
 23 25  1  0
 12 11  1  0
 25 26  1  0
 11  9  1  0
 16 17  1  0
  9  8  1  0
 14 15  2  0
  8 31  1  0
 23 24  1  0
 18 30  1  0
 12 13  1  6
  9 10  2  0
  8 41  1  6
 18 19  1  0
 31 58  1  6
  8  6  1  0
 25 27  1  0
 29 57  1  0
 19 45  1  0
  4 37  1  1
  2 35  1  6
  1 32  1  0
  1 33  1  0
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  3 36  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  1
 25 52  1  6
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 26 55  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 27 56  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.705   4.966   2.442  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.998   3.544   1.978  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.528   3.615   0.648  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.020   2.813   2.859  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.660   2.804   4.343  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.123   1.377   2.355  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.341   0.505   2.736  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.235   1.066   1.378  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.396   0.459   2.098  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.093   1.046   2.911  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.587  -0.834   1.717  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.511  -1.259   0.875  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.093  -2.191  -0.191  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.448  -2.045   1.653  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.744  -2.694   2.657  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.055  -2.056   1.097  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -0.033  -3.321   1.701  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      -0.661  -1.138   0.186  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.693  -1.138  -0.384  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.036  -0.218  -1.305  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.358  -0.171  -1.900  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.757   0.704  -2.840  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.151   0.720  -3.436  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.058   0.558  -4.955  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.965   1.979  -3.043  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.319   3.317  -3.389  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.236   1.960  -1.637  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.146   0.758  -1.743  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.118   0.790  -1.193  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.568  -0.070  -0.263  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.961   0.029   0.288  0.00  0.00           C+0
HETATM   32  H   UNK     0      -0.207   4.983   3.416  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.056   5.479   1.723  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.628   5.554   2.506  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.061   2.976   1.924  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.864   4.074   0.101  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.011   3.272   2.752  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.752   3.804   4.778  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.634   2.454   4.504  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.327   2.139   4.902  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.569   1.991   0.895  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.339  -2.513  -0.916  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.519  -3.088   0.272  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.913  -1.705  -0.733  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.416  -1.879  -0.059  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.070  -0.913  -1.541  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.058   1.447  -3.219  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.701  -0.149  -3.049  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.475   1.360  -5.420  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.056   0.558  -5.408  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.577  -0.392  -5.215  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.941   1.932  -3.539  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.116   3.407  -4.460  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.984   4.138  -3.098  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.387   3.471  -2.836  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.380   1.930  -1.175  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.687   1.612  -1.608  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.619   0.306  -0.552  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    4    1    3   35                                             
CONECT    3    2   36                                                       
CONECT    4    6    2    5   37                                             
CONECT    5    4   38   39   40                                             
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    9   31   41    6                                             
CONECT    9   11    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12    9                                                       
CONECT   12   31   14   11   13                                             
CONECT   13   12   42   43   44                                             
CONECT   14   12   16   15                                                  
CONECT   15   14                                                            
CONECT   16   14   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   30   19                                                  
CONECT   19   20   18   45                                                  
CONECT   20   28   19   21                                                  
CONECT   21   20   22   46                                                  
CONECT   22   21   23   47                                                  
CONECT   23   22   25   24   48                                             
CONECT   24   23   49   50   51                                             
CONECT   25   23   26   27   52                                             
CONECT   26   25   53   54   55                                             
CONECT   27   25   56                                                       
CONECT   28   29   20                                                       
CONECT   29   30   28   57                                                  
CONECT   30   29   31   18                                                  
CONECT   31   12   30    8   58                                             
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    8                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   19                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   29                                                            
CONECT   58   31                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

RDKit          3D

58 60  0  0  0  0  0  0  0  0999 V2000
   -0.7048    4.9665    2.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9978    3.5440    1.9784 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5278    3.6149    0.6482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204    2.8127    2.8591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6595    2.8043    4.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1229    1.3767    2.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3407    0.5048    2.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2350    1.0658    1.3776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3957    0.4590    2.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0929    1.0458    2.9106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871   -0.8343    1.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5107   -1.2586    0.8752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0932   -2.1905   -0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483   -2.0452    1.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7436   -2.6944    2.6572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554   -2.0558    1.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -3.3209    1.7008 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6607   -1.1381    0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -1.1379   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -0.2181   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3584   -0.1705   -1.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570    0.7039   -2.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514    0.7198   -3.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0581    0.5578   -4.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647    1.9791   -3.0426 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3191    3.3167   -3.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359    1.9603   -1.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1458    0.7583   -1.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1179    0.7904   -1.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677   -0.0697   -0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9607    0.0293    0.2882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2072    4.9827    3.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564    5.4791    1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275    5.5537    2.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612    2.9761    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    4.0743    0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0110    3.2725    2.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7518    3.8043    4.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6339    2.4544    4.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    2.1391    4.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5689    1.9908    0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386   -2.5129   -0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5189   -3.0885    0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9127   -1.7048   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4155   -1.8788   -0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704   -0.9126   -1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0579    1.4471   -3.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7014   -0.1492   -3.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750    1.3601   -5.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    0.5580   -5.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -0.3922   -5.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9410    1.9317   -3.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1164    3.4068   -4.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838    4.1380   -3.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3872    3.4714   -2.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797    1.9303   -1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874    1.6117   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    0.3060   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  2  0
  6  4  1  0
 29 28  1  0
  4  2  1  0
 28 20  1  0
  2  1  1  0
 20 19  2  0
  6  7  2  0
 31 12  1  0
  4  5  1  0
  2  3  1  0
 14 12  1  0
 20 21  1  0
 14 16  1  0
 21 22  2  0
 31 30  1  0
 22 23  1  0
 18 16  2  0
 23 25  1  0
 12 11  1  0
 25 26  1  0
 11  9  1  0
 16 17  1  0
  9  8  1  0
 14 15  2  0
  8 31  1  0
 23 24  1  0
 18 30  1  0
 12 13  1  6
  9 10  2  0
  8 41  1  6
 18 19  1  0
 31 58  1  6
  8  6  1  0
 25 27  1  0
 29 57  1  0
 19 45  1  0
  4 37  1  1
  2 35  1  6
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 38  1  0
  5 39  1  0
  5 40  1  0
  3 36  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  1
 25 52  1  6
 26 53  1  0
 26 54  1  0
 26 55  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 27 56  1  0
M  END

View in JSmol

Synonyms

Value	Source
12b-Hydroxychaetoviridin C	Generator
12Β-hydroxychaetoviridin C	Generator

Chemical Formula

C₂₃H₂₇ClO₇

Average Mass

450.9100 Da

Monoisotopic Mass

450.14453 Da

IUPAC Name

(6aS,9R,9aS)-5-chloro-9-[(2S,3S)-3-hydroxy-2-methylbutanoyl]-3-[(1E,3R,4R)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione

Traditional Name

(6aS,9R,9aS)-5-chloro-9-[(2S,3S)-3-hydroxy-2-methylbutanoyl]-3-[(1E,3R,4R)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9H,9aH-furo[2,3-h]isochromene-6,8-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@]([H])(C([H])([H])[H])[C@@]([H])(C(\[H])=C(/[H])C1=C([H])C2=C(Cl)C(=O)[C@]3(OC(=O)[C@@]([H])(C(=O)[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[H])[C@@]3([H])C2=C([H])O1)C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H27ClO7/c1-10(12(3)25)6-7-14-8-15-16(9-30-14)18-17(20(27)11(2)13(4)26)22(29)31-23(18,5)21(28)19(15)24/h6-13,17-18,25-26H,1-5H3/b7-6+/t10-,11+,12-,13+,17-,18-,23+/m1/s1

InChI Key

MEPQPODJTXSHEP-HETSEVKPSA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chaetomium globosum	JEOL database	Borges, W. S., et al, J. Nat. Prod. 74, 1182 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha-acyloxy ketone
Beta-hydroxy ketone
Gamma butyrolactone
Pyran
1,3-dicarbonyl compound
Alpha-haloketone
Alpha-chloroketone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Chloroalkene
Monocarboxylic acid or derivatives
Haloalkene
Organoheterocyclic compound
Vinyl chloride
Vinyl halide
Organohalogen compound
Organochloride
Hydrocarbon derivative
Organic oxide
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:67618 )
secondary alcohol (CHEBI:67618 )
organochlorine compound (CHEBI:67618 )
enone (CHEBI:67618 )
gamma-lactone (CHEBI:67618 )
beta-hydroxy ketone (CHEBI:67618 )
azaphilone (CHEBI:67618 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.38	ALOGPS
logP	1.9	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.74	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	117.85 m³·mol⁻¹	ChemAxon
Polarizability	45.8 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052544

Chemspider ID

26631628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

67618

Good Scents ID

Not Available

References

General References

Borges WS, Mancilla G, Guimaraes DO, Duran-Patron R, Collado IG, Pupo MT: Azaphilones from the endophyte Chaetomium globosum. J Nat Prod. 2011 May 27;74(5):1182-7. doi: 10.1021/np200110f. Epub 2011 May 6. [PubMed:21548578 ]
Borges, W. S., et al. (2011). Borges, W. S., et al, J. Nat. Prod. 74, 1182 (2011). J. Nat. Prod..

Showing NP-Card for 12beta-hydroxychaetoviridin C (NP0035956)

MOL for NP0035956 (12beta-hydroxychaetoviridin C)

3D MOL for NP0035956 (12beta-hydroxychaetoviridin C)

3D SDF for NP0035956 (12beta-hydroxychaetoviridin C)

3D-SDF for NP0035956 (12beta-hydroxychaetoviridin C)

PDB for NP0035956 (12beta-hydroxychaetoviridin C)

3D PDB for NP0035956 (12beta-hydroxychaetoviridin C)

SMILES for NP0035956 (12beta-hydroxychaetoviridin C)

INCHI for NP0035956 (12beta-hydroxychaetoviridin C)

Structure for NP0035956 (12beta-hydroxychaetoviridin C)

3D Structure for NP0035956 (12beta-hydroxychaetoviridin C)