NP-MRD: Showing NP-Card for Ascochlorin (NP0021366)

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Record Information

Version

2.0

Created at

2021-01-06 06:37:23 UTC

Updated at

2021-07-15 17:36:09 UTC

NP-MRD ID

NP0021366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ascochlorin

Provided By

NPAtlas

Description

Ascochlorin is also known as ilicicolin D or LL-Z 1272 gamma. Ascochlorin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Ascochlorin is found in Ascochyta viciae, Cylindrocladium iliciola, Gliomastix luzulae and Nigrosabulum globosum. It was first documented in 1968 (PMID: 4304615). Based on a literature review a significant number of articles have been published on ascochlorin (PMID: 11374942) (PMID: 11029223) (PMID: 19253369) (PMID: 20025846).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120423D          

 57 58  0  0  0  0            999 V2000
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   -5.3919    0.6172    1.3084 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  9 10  1  0  0  0  0
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  2 15  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242120423D          

 57 58  0  0  0  0            999 V2000
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    0.3674   -0.4015    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8659   -1.1762   -0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9945    0.9413    1.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010   -0.0494   -2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.4511   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6187    0.0804   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4925   -1.9186    0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9410   -0.4143   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8385   -1.6020   -1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7671   -2.0943   -0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -0.1565    1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8729   -1.3873    1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4145    1.2106    2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4371    0.2089    1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1068    2.2174   -0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7923    2.7802   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9627    1.1075   -2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3762    1.9842   -2.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -1.8674   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -0.5551    2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8007   -2.2363    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2036   -3.7264   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0334    1.0540   -2.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4818   -0.7155   -2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0323    0.4367   -1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    2.8647    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1037    2.2367    1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 13  5  1  0  0  0  0
 27 17  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  0  0  0  0
  6 34  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  7 37  1  1  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  9 41  1  0  0  0  0
  9 42  1  0  0  0  0
 10 43  1  0  0  0  0
 10 44  1  0  0  0  0
 13 45  1  1  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 14 48  1  0  0  0  0
 15 49  1  0  0  0  0
 16 50  1  0  0  0  0
 16 51  1  0  0  0  0
 19 52  1  0  0  0  0
 23 53  1  0  0  0  0
 23 54  1  0  0  0  0
 23 55  1  0  0  0  0
 25 56  1  0  0  0  0
 28 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(O[H])=C(C([H])=O)C(=C1Cl)C([H])([H])[H])C([H])([H])C(\[H])=C(\C(\[H])=C(/[H])[C@]1(C([H])([H])[H])[C@]([H])(C(=O)C([H])([H])C([H])([H])[C@@]1([H])C([H])([H])[H])C([H])([H])[H])/C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H29ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10+,13-6+/t14-,16+,23+/m1/s1

> <INCHI_KEY>
SETVRSKZJJWOPA-FLDGXQSCSA-N

> <FORMULA>
C23H29ClO4

> <MOLECULAR_WEIGHT>
404.927

> <EXACT_MASS>
404.175437123

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.593174635879514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

> <ALOGPS_LOGP>
5.64

> <JCHEM_LOGP>
6.654268878666666

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.527442619948426

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.841100529614853

> <JCHEM_PKA_STRONGEST_BASIC>
-6.043439126273062

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
116.40119999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
    0.5210    0.4956    2.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674   -0.4015    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428   -0.4703    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    0.2245    0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1271    0.1070   -0.5410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6135   -0.3319   -1.9140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0368   -0.9529    0.0258 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2212   -1.2260   -0.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302   -0.5210    1.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3919    0.6172    1.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0048    1.5426    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7276    2.5295    0.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8366    1.4171   -0.6410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2545    1.7900   -2.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800   -1.1900    0.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6396   -1.1784    1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8192   -0.8587    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3521   -1.7621   -0.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8127   -3.0485   -0.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4456   -1.4250   -1.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1825   -2.5647   -2.1265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0080   -0.1569   -0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1962    0.2021   -1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4698    0.7934   -0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0761    2.1284    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0680    2.4897   -0.5842 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3725    0.4008    0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    1.3079    1.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5081    0.8811    2.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8691   -0.0114    3.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043    1.4001    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659   -1.1762   -0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9945    0.9413    1.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010   -0.0494   -2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.4511   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6187    0.0804   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4925   -1.9186    0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9410   -0.4143   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8385   -1.6020   -1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7671   -2.0943   -0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -0.1565    1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8729   -1.3873    1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4145    1.2106    2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4371    0.2089    1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1068    2.2174   -0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7923    2.7802   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9627    1.1075   -2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3762    1.9842   -2.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -1.8674   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -0.5551    2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8007   -2.2363    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2036   -3.7264   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0334    1.0540   -2.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4818   -0.7155   -2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0323    0.4367   -1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    2.8647    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1037    2.2367    1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  4  1  1
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
  2 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 24 27  2  0
 27 28  1  0
 13  5  1  0
 27 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  4 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  1
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 13 45  1  1
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 19 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 25 56  1  0
 28 57  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       0.521   0.496   2.141  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.367  -0.402   0.987  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.843  -0.470   0.169  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.926   0.225   0.328  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.127   0.107  -0.541  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.614  -0.332  -1.914  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.037  -0.953   0.026  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.221  -1.226  -0.852  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.430  -0.521   1.422  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.392   0.617   1.308  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.005   1.543   0.243  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.728   2.530   0.063  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.837   1.417  -0.641  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.255   1.790  -2.036  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.380  -1.190   0.669  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.640  -1.178   1.444  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.819  -0.859   0.604  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.352  -1.762  -0.245  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.813  -3.049  -0.377  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.446  -1.425  -1.001  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       6.183  -2.565  -2.127  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       6.008  -0.157  -0.897  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.196   0.202  -1.722  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.470   0.793  -0.022  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.076   2.128   0.077  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.068   2.490  -0.584  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.372   0.401   0.712  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.804   1.308   1.593  0.00  0.00           O+0
HETATM   29  H   UNK     0      -0.508   0.881   2.409  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.869  -0.011   3.069  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.104   1.400   1.958  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.866  -1.176  -0.676  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.994   0.941   1.127  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.301  -0.049  -2.726  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.501  -1.451  -1.848  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.619   0.080  -2.091  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.493  -1.919   0.138  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.941  -0.414  -0.925  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.838  -1.602  -1.819  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.767  -2.094  -0.385  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.512  -0.157   1.924  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.873  -1.387   1.956  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.415   1.211   2.269  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.437   0.209   1.189  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.107   2.217  -0.317  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.792   2.780  -1.951  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.963   1.107  -2.502  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.376   1.984  -2.689  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.271  -1.867  -0.196  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.636  -0.555   2.335  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.801  -2.236   1.800  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.204  -3.726  -1.007  0.00  0.00           H+0
HETATM   53  H   UNK     0       7.033   1.054  -2.388  0.00  0.00           H+0
HETATM   54  H   UNK     0       7.482  -0.716  -2.303  0.00  0.00           H+0
HETATM   55  H   UNK     0       8.032   0.437  -1.012  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.665   2.865   0.750  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.104   2.237   1.763  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3   15                                                  
CONECT    3    2    4   32                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6    7   13                                             
CONECT    6    5   34   35   36                                             
CONECT    7    5    8    9   37                                             
CONECT    8    7   38   39   40                                             
CONECT    9    7   10   41   42                                             
CONECT   10    9   11   43   44                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14    5   45                                             
CONECT   14   13   46   47   48                                             
CONECT   15    2   16   49                                                  
CONECT   16   15   17   50   51                                             
CONECT   17   16   18   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   52                                                       
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22   53   54   55                                             
CONECT   24   22   25   27                                                  
CONECT   25   24   26   56                                                  
CONECT   26   25                                                            
CONECT   27   24   28   17                                                  
CONECT   28   27   57                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    6                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   10                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   19                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   25                                                            
CONECT   57   28                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  116    0
END

RDKit          3D

57 58  0  0  0  0  0  0  0  0999 V2000
    0.5210    0.4956    2.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674   -0.4015    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0048    1.5426    0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8366    1.4171   -0.6410 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.8192   -0.8587    0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1825   -2.5647   -2.1265 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0080   -0.1569   -0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1962    0.2021   -1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4698    0.7934   -0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0761    2.1284    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0680    2.4897   -0.5842 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3725    0.4008    0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    1.3079    1.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8691   -0.0114    3.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043    1.4001    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659   -1.1762   -0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9945    0.9413    1.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3010   -0.0494   -2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.4511   -1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6187    0.0804   -2.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4925   -1.9186    0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9410   -0.4143   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8385   -1.6020   -1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7671   -2.0943   -0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -0.1565    1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8729   -1.3873    1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4145    1.2106    2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4371    0.2089    1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1068    2.2174   -0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7923    2.7802   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9627    1.1075   -2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3762    1.9842   -2.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -1.8674   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -0.5551    2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8007   -2.2363    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2036   -3.7264   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0334    1.0540   -2.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4818   -0.7155   -2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0323    0.4367   -1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    2.8647    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1037    2.2367    1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  4  1  1
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
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  2 15  2  0
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 13  5  1  0
 27 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  4 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  1
  8 38  1  0
  8 39  1  0
  8 40  1  0
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  9 42  1  0
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 15 49  1  0
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 19 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 25 56  1  0
 28 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Ascochlorin	ChEBI
Antibiotic LL-Z1272 gamma	ChEBI
Antibiotic LL-Z1272gamma	ChEBI
Ilicicolin D	ChEBI
LL-Z 1272 gamma	ChEBI
Antibiotic LL-Z1272 g	Generator
Antibiotic LL-Z1272 γ	Generator
Antibiotic LL-Z1272g	Generator
Antibiotic LL-Z1272γ	Generator
LL-Z 1272 g	Generator
LL-Z 1272 Γ	Generator

Chemical Formula

C₂₃H₂₉ClO₄

Average Mass

404.9270 Da

Monoisotopic Mass

404.17544 Da

IUPAC Name

3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

Traditional Name

3-chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCC(=O)[C@H](C)[C@@]1(C)\C=C\C(\C)=C\CC1=C(O)C(C=O)=C(C)C(Cl)=C1O

InChI Identifier

InChI=1S/C23H29ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10+,13-6+/t14-,16+,23+/m1/s1

InChI Key

SETVRSKZJJWOPA-FLDGXQSCSA-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
Ascochyta viciae	NPAtlas	4304615
Cylindrocladium iliciola	-	KNApSAcK
Gliomastix luzulae	LOTUS Database	35616633
Nigrosabulum globosum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Acremonium lazulae	KNApSAcK Database	22123792
Acremonium luzulae	KNApSAcK Database	22123792
Acremonium sp.	KNApSAcK Database	22123792
Fusarium sp.	KNApSAcK Database	22123792
Nectria coccinea	KNApSAcK Database	22123792
Nectria lucida	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
4-halophenol
2-halophenol
M-cresol
2-chlorophenol
Benzoyl
4-chlorophenol
Resorcinol
Halobenzene
Chlorobenzene
Toluene
Phenol
Benzenoid
Aryl halide
Monocyclic benzene moiety
Aryl chloride
Vinylogous acid
Cyclic ketone
Ketone
Organochloride
Hydrocarbon derivative
Organohalogen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	5.64	ALOGPS
logP	6.65	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	5.84	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	116.4 m³·mol⁻¹	ChemAxon
Polarizability	44.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA021230

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018754

Chemspider ID

9433253

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11258227

PDB ID

Not Available

ChEBI ID

156219

Good Scents ID

Not Available

References

General References

Che Y, Swenson DC, Gloer JB, Koster B, Malloch D: Pseudodestruxins A and B: new cyclic depsipeptides from the coprophilous fungus Nigrosabulum globosum. J Nat Prod. 2001 May;64(5):555-8. doi: 10.1021/np000547r. [PubMed:11374942 ]
Tamura G, Suzuki S, Takatsuki A, Ando K, Arima K: Ascochlorin, a new antibiotic, found by the paper-disc agar-diffusion method. I. Isolation, biological and chemical properties of ascochlorin. (Studies on antiviral and antitumor antibiotics. I). J Antibiot (Tokyo). 1968 Sep;21(9):539-44. doi: 10.7164/antibiotics.21.539. [PubMed:4304615 ]
Dudley GB, Takaki KS, Cha DD, Danheiser RL: Total synthesis of (-)-ascochlorin via a cyclobutenone-based benzannulation strategy. Org Lett. 2000 Oct 19;2(21):3407-10. doi: 10.1021/ol006561c. [PubMed:11029223 ]
Jeong JH, Nakajima H, Magae J, Furukawa C, Taki K, Otsuka K, Tomita M, Lee IS, Kim CH, Chang HW, Min KS, Park KK, Park KK, Chang YC: Ascochlorin activates p53 in a manner distinct from DNA damaging agents. Int J Cancer. 2009 Jun 15;124(12):2797-803. doi: 10.1002/ijc.24259. [PubMed:19253369 ]
Berry EA, Huang LS, Lee DW, Daldal F, Nagai K, Minagawa N: Ascochlorin is a novel, specific inhibitor of the mitochondrial cytochrome bc1 complex. Biochim Biophys Acta. 2010 Mar;1797(3):360-70. doi: 10.1016/j.bbabio.2009.12.003. Epub 2009 Dec 16. [PubMed:20025846 ]

Showing NP-Card for Ascochlorin (NP0021366)

MOL for NP0021366 (Ascochlorin)

3D MOL for NP0021366 (Ascochlorin)

3D SDF for NP0021366 (Ascochlorin)

3D-SDF for NP0021366 (Ascochlorin)

PDB for NP0021366 (Ascochlorin)

3D PDB for NP0021366 (Ascochlorin)

SMILES for NP0021366 (Ascochlorin)

INCHI for NP0021366 (Ascochlorin)

Structure for NP0021366 (Ascochlorin)

3D Structure for NP0021366 (Ascochlorin)