NP-MRD: Showing NP-Card for 5-Chloroisorotiorin (NP0022282)

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Record Information

Version

2.0

Created at

2021-01-06 07:29:37 UTC

Updated at

2021-07-15 17:38:37 UTC

NP-MRD ID

NP0022282

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Chloroisorotiorin

Provided By

NPAtlas

Description

5-Chloroisorotiorin is found in Penicillium and Penicillium sclerotiorum. 5-Chloroisorotiorin was first documented in 1995 (PMID: 7592055). Based on a literature review very few articles have been published on (6aR)-9-acetyl-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105223D          

 52 54  0  0  0  0            999 V2000
    6.0123   -1.2908   -1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3336   -1.9442   -0.6628 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8423   -1.1106    0.5121 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2066   -1.8345    1.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -0.9954    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971    0.1555    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716    1.3667    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280    0.1683    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099    0.1813    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2604    0.1773   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8436    1.4430   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604    1.6264   -0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770    2.7983   -0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8759    4.2448   -0.2691 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245    2.8785   -0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9099    3.9040   -0.0764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0046    1.6970   -1.0901 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.3712    1.6348   -0.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6727    0.5653   -0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5082   -0.7907   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296   -0.8853   -0.1273 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9295   -1.4353   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5457   -1.8725   -2.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7964   -1.8971    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867    2.2432    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2021    1.3042    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0507   -1.6877   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  3  0  0  0
  9 10  1  0  0  0  0
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  2 33  1  0  0  0  0
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  3 35  1  1  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
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  9 44  1  0  0  0  0
 11 45  1  0  0  0  0
 18 46  1  0  0  0  0
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 18 48  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 28 52  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242105223D          

 52 54  0  0  0  0            999 V2000
    6.0123   -1.2908   -1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2274   -1.2346    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    2.3105   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896    2.5477   -2.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    1.0030   -2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2277    0.9507   -3.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2129   -1.0125    2.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4246   -2.6989    2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3645   -2.0727    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507   -1.6877   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  3  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 22 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 10  1  0  0  0  0
 27 12  1  0  0  0  0
 26 17  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
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  3 35  1  1  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
  7 42  1  0  0  0  0
  8 43  1  0  0  0  0
  9 44  1  0  0  0  0
 11 45  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 28 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022282

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=C([H])C1=C([H])C2=C(Cl)C(=O)[C@@]3(OC(=O)C(C(=O)C([H])([H])[H])=C3C2=C([H])O1)C([H])([H])[H])C(=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-28-15)19-18(14(4)25)22(27)29-23(19,5)21(26)20(16)24/h7-12H,6H2,1-5H3/b8-7?,13-9+/t12-,23+/m0/s1

> <INCHI_KEY>
QJSWSNAZIVGTFZ-UNSJDTSZSA-N

> <FORMULA>
C23H23ClO5

> <MOLECULAR_WEIGHT>
414.88

> <EXACT_MASS>
414.1234015

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
44.89952540451971

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6aR)-9-acetyl-5-chloro-3-[(3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
3.7965074753333323

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.282705471633466

> <JCHEM_PKA_STRONGEST_BASIC>
-5.231760847526595

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
115.91479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aR)-9-acetyl-5-chloro-3-[(3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methylfuro[2,3-h]isochromene-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    6.0123   -1.2908   -1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3336   -1.9442   -0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8423   -1.1106    0.5121 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2066   -1.8345    1.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -0.9954    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971    0.1555    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716    1.3667    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280    0.1683    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099    0.1813    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2604    0.1773   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8436    1.4430   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604    1.6264   -0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770    2.7983   -0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8759    4.2448   -0.2691 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245    2.8785   -0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9099    3.9040   -0.0764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0046    1.6970   -1.0901 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5581    1.5776   -2.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3712    1.6348   -0.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6727    0.5653   -0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8623    0.2488    0.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207   -0.1298    0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4074   -1.2524    1.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6923   -1.8210    1.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3612   -1.8156    1.5558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4878    0.5450   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528    0.3757   -0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5082   -0.7907   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296   -0.8853   -0.1273 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404   -0.2416   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9295   -1.4353   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5457   -1.8725   -2.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4215   -2.0699   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8439   -2.9209   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3762   -0.1391    0.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4638   -1.0391    2.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0719   -2.4743    1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3045   -2.4137    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7964   -1.8971    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867    2.2432    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2021    1.3042    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0929    1.5746   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    1.5583    0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -1.2346    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    2.3105   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896    2.5477   -2.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    1.0030   -2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2277    0.9507   -3.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2129   -1.0125    2.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4246   -2.6989    2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3645   -2.0727    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507   -1.6877   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 22 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 10  1  0
 27 12  1  0
 26 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  1
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
 11 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 28 52  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       6.012  -1.291  -1.978  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.334  -1.944  -0.663  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.842  -1.111   0.512  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.207  -1.835   1.784  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.397  -0.995   0.396  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.697   0.156   0.339  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.572   1.367   0.410  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.328   0.168   0.207  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.110   0.181   0.089  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.260   0.177  -0.043  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.844   1.443  -0.096  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.260   1.626  -0.226  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.877   2.798  -0.316  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -1.876   4.245  -0.269  0.00  0.00          Cl+0
HETATM   15  C   UNK     0      -4.324   2.878  -0.466  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.910   3.904  -0.076  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.005   1.697  -1.090  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.558   1.578  -2.506  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.371   1.635  -0.906  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.673   0.565  -0.085  0.00  0.00           C+0
HETATM   21  O   UNK     0      -7.862   0.249   0.270  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.421  -0.130   0.302  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.407  -1.252   1.192  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.692  -1.821   1.745  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.361  -1.816   1.556  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.488   0.545  -0.298  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.053   0.376  -0.295  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.508  -0.791  -0.253  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.130  -0.885  -0.127  0.00  0.00           O+0
HETATM   30  H   UNK     0       6.340  -0.242  -1.964  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.930  -1.435  -2.169  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.546  -1.873  -2.779  0.00  0.00           H+0
HETATM   33  H   UNK     0       7.422  -2.070  -0.552  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.844  -2.921  -0.623  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.376  -0.139   0.506  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.464  -1.039   2.536  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.072  -2.474   1.588  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.305  -2.414   2.103  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.796  -1.897   0.347  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.887   2.243   0.618  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.202   1.304   1.317  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.093   1.575  -0.523  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.235   1.558   0.204  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.227  -1.235   0.091  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.206   2.311  -0.041  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.290   2.548  -2.975  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.580   1.003  -2.490  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.228   0.951  -3.115  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.213  -1.012   2.304  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.425  -2.699   2.354  0.00  0.00           H+0
HETATM   51  H   UNK     0      -7.364  -2.073   0.905  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.051  -1.688  -0.316  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   33   34                                             
CONECT    3    2    4    5   35                                             
CONECT    4    3   36   37   38                                             
CONECT    5    3    6   39                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   40   41   42                                             
CONECT    8    6    9   43                                                  
CONECT    9    8   10   44                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12   45                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   26                                             
CONECT   18   17   46   47   48                                             
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   49   50   51                                             
CONECT   25   23                                                            
CONECT   26   22   27   17                                                  
CONECT   27   26   28   12                                                  
CONECT   28   27   29   52                                                  
CONECT   29   28   10                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42    7                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45   11                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   28                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

RDKit          3D

52 54  0  0  0  0  0  0  0  0999 V2000
    6.0123   -1.2908   -1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3336   -1.9442   -0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8423   -1.1106    0.5121 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2066   -1.8345    1.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -0.9954    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971    0.1555    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716    1.3667    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280    0.1683    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099    0.1813    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2604    0.1773   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8436    1.4430   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604    1.6264   -0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770    2.7983   -0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8759    4.2448   -0.2691 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245    2.8785   -0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9099    3.9040   -0.0764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0046    1.6970   -1.0901 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5581    1.5776   -2.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3712    1.6348   -0.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6727    0.5653   -0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8623    0.2488    0.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207   -0.1298    0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4074   -1.2524    1.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6923   -1.8210    1.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3612   -1.8156    1.5558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4878    0.5450   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528    0.3757   -0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5082   -0.7907   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296   -0.8853   -0.1273 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404   -0.2416   -1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9295   -1.4353   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5457   -1.8725   -2.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4215   -2.0699   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8439   -2.9209   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3762   -0.1391    0.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4638   -1.0391    2.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0719   -2.4743    1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3045   -2.4137    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7964   -1.8971    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867    2.2432    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2021    1.3042    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0929    1.5746   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    1.5583    0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -1.2346    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    2.3105   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2896    2.5477   -2.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802    1.0030   -2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2277    0.9507   -3.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2129   -1.0125    2.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4246   -2.6989    2.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3645   -2.0727    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507   -1.6877   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 22 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 10  1  0
 27 12  1  0
 26 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  1
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
 11 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 28 52  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₃H₂₃ClO₅

Average Mass

414.8800 Da

Monoisotopic Mass

414.12340 Da

IUPAC Name

(6aR)-9-acetyl-5-chloro-3-[(3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

Traditional Name

(6aR)-9-acetyl-5-chloro-3-[(3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methylfuro[2,3-h]isochromene-6,8-dione

CAS Registry Number

Not Available

SMILES

CC[C@H](C)\C=C(/C)\C=C\C1=CC2=C(Cl)C(=O)[C@]3(C)OC(=O)C(C(C)=O)=C3C2=CO1

InChI Identifier

InChI=1S/C23H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-28-15)19-18(14(4)25)22(27)29-23(19,5)21(26)20(16)24/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,23+/m0/s1

InChI Key

QJSWSNAZIVGTFZ-UNSJDTSZSA-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
Penicillium	NPAtlas	7592055
Penicillium sclerotiorum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Chaetomium cupreum CC3003	KNApSAcK Database	22123792
Penicillium hirayamae Udagawa	KNApSAcK Database	22123792
Penicillium hirayamae Van Beyma	KNApSAcK Database	22123792
Penicillium multicolor FO-2338	KNApSAcK Database	22123792
Penicillium sclerotiorum X11853	KNApSAcK Database	22123792
Penicillium sp. FO-4164	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.66	ALOGPS
logP	3.8	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	18.28	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.91 m³·mol⁻¹	ChemAxon
Polarizability	44.9 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

NPAtlas ID

NPA014125

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052733

Chemspider ID

8539944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10364495

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pairet L, Wrigley SK, Chetland I, Reynolds EE, Hayes MA, Holloway J, Ainsworth AM, Katzer W, Cheng XM, Hupe DJ, et al.: Azaphilones with endothelin receptor binding activity produced by Penicillium sclerotiorum: taxonomy, fermentation, isolation, structure elucidation and biological activity. J Antibiot (Tokyo). 1995 Sep;48(9):913-23. doi: 10.7164/antibiotics.48.913. [PubMed:7592055 ]

Showing NP-Card for 5-Chloroisorotiorin (NP0022282)

MOL for NP0022282 (5-Chloroisorotiorin)

3D MOL for NP0022282 (5-Chloroisorotiorin)

3D SDF for NP0022282 (5-Chloroisorotiorin)

3D-SDF for NP0022282 (5-Chloroisorotiorin)

PDB for NP0022282 (5-Chloroisorotiorin)

3D PDB for NP0022282 (5-Chloroisorotiorin)

SMILES for NP0022282 (5-Chloroisorotiorin)

INCHI for NP0022282 (5-Chloroisorotiorin)

Structure for NP0022282 (5-Chloroisorotiorin)

3D Structure for NP0022282 (5-Chloroisorotiorin)