NP-MRD: Showing NP-Card for chaetomugilin J (NP0038550)

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Record Information

Version

2.0

Created at

2021-06-20 21:12:44 UTC

Updated at

2021-06-30 00:11:24 UTC

NP-MRD ID

NP0038550

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chaetomugilin J

Provided By

JEOL Database JEOL Logo

Description

(7S,8S)-5-chloro-7-hydroxy-7-methyl-8-[(3E)-3-methyl-2-oxopent-3-en-1-yl]-3-[(1E,3S)-3-methylpent-1-en-1-yl]-7,8-dihydro-6H-isochromen-6-one 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. chaetomugilin J is found in Chaetomium species and Mugil cephalus. chaetomugilin J was first documented in 2009 (Muroga, Y., et al.). Based on a literature review very few articles have been published on (7S,8S)-5-chloro-7-hydroxy-7-methyl-8-[(3E)-3-methyl-2-oxopent-3-en-1-yl]-3-[(1E,3S)-3-methylpent-1-en-1-yl]-7,8-dihydro-6H-isochromen-6-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123123D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202123123D          

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    0.0031    5.1239   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    6.6239    2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4915    7.4450    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064    8.6599    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640    7.7335   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735    7.9897    1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264    6.9513   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8722    5.0115    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329    6.0208    2.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9926    6.3780    0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8926    2.1180    3.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2175   -0.0508    0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945   -1.6594    0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4315   -1.1919   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -3.5471    0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 19  2  0  0  0  0
 13 14  2  0  0  0  0
 11 10  1  0  0  0  0
 14 15  1  0  0  0  0
 10  9  2  0  0  0  0
 15 17  1  0  0  0  0
 20 19  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
  7  5  1  0  0  0  0
  8 25  1  0  0  0  0
  5  3  1  0  0  0  0
 25 23  1  0  0  0  0
  3  2  2  0  0  0  0
 23 21  1  0  0  0  0
  2  1  1  0  0  0  0
 20  9  1  0  0  0  0
  3  4  1  0  0  0  0
 21 22  1  0  0  0  0
  5  6  2  0  0  0  0
 15 16  1  0  0  0  0
 23 24  2  0  0  0  0
  8 37  1  6  0  0  0
 12 11  1  0  0  0  0
 25 26  1  0  0  0  0
 12 13  1  0  0  0  0
 25 27  1  6  0  0  0
 10 38  1  0  0  0  0
 19 50  1  0  0  0  0
 13 39  1  0  0  0  0
 14 40  1  0  0  0  0
 15 41  1  1  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
 18 49  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  2 31  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
 16 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
 27 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(C(=O)C(Cl)=C2C([H])=C(OC([H])=C2[C@]1([H])C([H])([H])C(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C(\[H])=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H27ClO4/c1-6-13(3)8-9-15-10-16-17(12-27-15)18(11-19(24)14(4)7-2)22(5,26)21(25)20(16)23/h7-10,12-13,18,26H,6,11H2,1-5H3/b9-8+,14-7+/t13-,18-,22-/m0/s1

> <INCHI_KEY>
DIBDMIBWFDRKHK-ODXBHRCKSA-N

> <FORMULA>
C22H27ClO4

> <MOLECULAR_WEIGHT>
390.9

> <EXACT_MASS>
390.159787

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.75385455818873

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7S,8S)-5-chloro-7-hydroxy-7-methyl-8-[(3E)-3-methyl-2-oxopent-3-en-1-yl]-3-[(1E,3S)-3-methylpent-1-en-1-yl]-7,8-dihydro-6H-isochromen-6-one

> <ALOGPS_LOGP>
4.48

> <JCHEM_LOGP>
4.04724208

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.47035794737261

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.874338108991612

> <JCHEM_PKA_STRONGEST_BASIC>
-3.728541289546759

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
112.66069999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7S,8S)-5-chloro-7-hydroxy-7-methyl-8-[(3E)-3-methyl-2-oxopent-3-en-1-yl]-3-[(1E,3S)-3-methylpent-1-en-1-yl]-8H-isochromen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
   -1.9604   -5.6008   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -4.3242   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2166   -4.1493   -1.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8670   -2.5009   -2.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3400   -1.7580   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582   -0.9492   -0.4065 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3880    0.4227    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876    1.4754   -0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781    2.7338   -0.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    2.9194    1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2451    4.2359    1.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658    5.2536    0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5210    6.6117    1.3276 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.9212    6.9655    0.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0136    6.0358    1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781    1.9399    2.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4387    0.6371    1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8863   -0.3312    2.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327   -0.1868    4.1776 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4253   -1.6150    1.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6453   -2.5902    2.6268 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7461   -1.6849    0.4035 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1444   -1.1028    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7946   -3.0627    0.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -5.8900    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654   -6.4335   -0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364   -5.4503   -0.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -3.4727   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5104   -5.1326   -2.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977   -5.1190   -3.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769   -6.2277   -1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5147   -1.1049   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1452   -2.2443    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440   -0.8177   -1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0269    1.4513   -1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1677    4.3909    2.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    5.1239   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    6.6239    2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4915    7.4450    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064    8.6599    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640    7.7335   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735    7.9897    1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264    6.9513   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8722    5.0115    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329    6.0208    2.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9926    6.3780    0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8926    2.1180    3.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2175   -0.0508    0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945   -1.6594    0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4315   -1.1919   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -3.5471    0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 19  2  0
 13 14  2  0
 11 10  1  0
 14 15  1  0
 10  9  2  0
 15 17  1  0
 20 19  1  0
 17 18  1  0
 20 21  2  0
  8  7  1  0
  9  8  1  0
  7  5  1  0
  8 25  1  0
  5  3  1  0
 25 23  1  0
  3  2  2  0
 23 21  1  0
  2  1  1  0
 20  9  1  0
  3  4  1  0
 21 22  1  0
  5  6  2  0
 15 16  1  0
 23 24  2  0
  8 37  1  6
 12 11  1  0
 25 26  1  0
 12 13  1  0
 25 27  1  6
 10 38  1  0
 19 50  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  1
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
  7 35  1  0
  7 36  1  0
  2 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  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      -1.960  -5.601  -0.247  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.238  -4.324  -0.545  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.217  -4.149  -1.406  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.418  -5.217  -2.250  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.382  -2.783  -1.615  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.867  -2.501  -2.713  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.340  -1.758  -0.489  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.658  -0.949  -0.407  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.388   0.423   0.171  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.088   1.475  -0.609  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.778   2.734  -0.135  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.682   2.919   1.242  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.245   4.236   1.667  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.066   5.254   0.846  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.521   6.612   1.328  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.493   7.671   0.889  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.921   6.965   0.794  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.014   6.036   1.308  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.978   1.940   2.117  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.439   0.637   1.624  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.886  -0.331   2.451  0.00  0.00           C+0
HETATM   22 Cl   UNK     0       1.933  -0.187   4.178  0.00  0.00          Cl+0
HETATM   23  C   UNK     0       2.425  -1.615   1.903  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.645  -2.590   2.627  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.746  -1.685   0.404  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.144  -1.103   0.172  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.795  -3.063   0.012  0.00  0.00           O+0
HETATM   28  H   UNK     0      -1.786  -5.890   0.794  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.665  -6.434  -0.888  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.036  -5.450  -0.382  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.644  -3.473  -0.003  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.510  -5.133  -2.215  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.098  -5.119  -3.292  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.177  -6.228  -1.914  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.515  -1.105  -0.706  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.145  -2.244   0.472  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.044  -0.818  -1.427  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.027   1.451  -1.690  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.168   4.391   2.742  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.003   5.124  -0.233  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.559   6.624   2.425  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.492   7.445   1.280  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.206   8.660   1.264  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.564   7.734  -0.203  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.174   7.990   1.096  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.926   6.951  -0.304  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.872   5.011   0.950  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.033   6.021   2.402  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.993   6.378   0.957  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.893   2.118   3.184  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.218  -0.051   0.465  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.894  -1.659   0.747  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.431  -1.192  -0.882  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.212  -3.547   0.754  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1   31                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3   32   33   34                                             
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5   35   36                                             
CONECT    8    7    9   25   37                                             
CONECT    9   10    8   20                                                  
CONECT   10   11    9   38                                                  
CONECT   11   10   12                                                       
CONECT   12   19   11   13                                                  
CONECT   13   14   12   39                                                  
CONECT   14   13   15   40                                                  
CONECT   15   14   17   16   41                                             
CONECT   16   15   42   43   44                                             
CONECT   17   15   18   45   46                                             
CONECT   18   17   47   48   49                                             
CONECT   19   12   20   50                                                  
CONECT   20   19   21    9                                                  
CONECT   21   20   23   22                                                  
CONECT   22   21                                                            
CONECT   23   25   21   24                                                  
CONECT   24   23                                                            
CONECT   25    8   23   26   27                                             
CONECT   26   25   51   52   53                                             
CONECT   27   25   54                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38   10                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   19                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
CONECT   54   27                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  110    0
END

RDKit          3D

54 55  0  0  0  0  0  0  0  0999 V2000
   -1.9604   -5.6008   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -4.3242   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2166   -4.1493   -1.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183   -5.2167   -2.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -2.7827   -1.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8670   -2.5009   -2.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3400   -1.7580   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582   -0.9492   -0.4065 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3880    0.4227    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876    1.4754   -0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781    2.7338   -0.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    2.9194    1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2451    4.2359    1.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658    5.2536    0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5210    6.6117    1.3276 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4929    7.6713    0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9212    6.9655    0.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0136    6.0358    1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781    1.9399    2.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4387    0.6371    1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8863   -0.3312    2.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327   -0.1868    4.1776 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4253   -1.6150    1.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6453   -2.5902    2.6268 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7461   -1.6849    0.4035 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1444   -1.1028    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7946   -3.0627    0.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -5.8900    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654   -6.4335   -0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364   -5.4503   -0.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -3.4727   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5104   -5.1326   -2.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977   -5.1190   -3.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769   -6.2277   -1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5147   -1.1049   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1452   -2.2443    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440   -0.8177   -1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0269    1.4513   -1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1677    4.3909    2.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    5.1239   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    6.6239    2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4915    7.4450    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064    8.6599    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640    7.7335   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735    7.9897    1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264    6.9513   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8722    5.0115    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329    6.0208    2.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9926    6.3780    0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8926    2.1180    3.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2175   -0.0508    0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945   -1.6594    0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4315   -1.1919   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -3.5471    0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 19  2  0
 13 14  2  0
 11 10  1  0
 14 15  1  0
 10  9  2  0
 15 17  1  0
 20 19  1  0
 17 18  1  0
 20 21  2  0
  8  7  1  0
  9  8  1  0
  7  5  1  0
  8 25  1  0
  5  3  1  0
 25 23  1  0
  3  2  2  0
 23 21  1  0
  2  1  1  0
 20  9  1  0
  3  4  1  0
 21 22  1  0
  5  6  2  0
 15 16  1  0
 23 24  2  0
  8 37  1  6
 12 11  1  0
 25 26  1  0
 12 13  1  0
 25 27  1  6
 10 38  1  0
 19 50  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  1
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
  7 35  1  0
  7 36  1  0
  2 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇ClO₄

Average Mass

390.9000 Da

Monoisotopic Mass

390.15979 Da

IUPAC Name

(7S,8S)-5-chloro-7-hydroxy-7-methyl-8-[(3E)-3-methyl-2-oxopent-3-en-1-yl]-3-[(1E,3S)-3-methylpent-1-en-1-yl]-7,8-dihydro-6H-isochromen-6-one

Traditional Name

(7S,8S)-5-chloro-7-hydroxy-7-methyl-8-[(3E)-3-methyl-2-oxopent-3-en-1-yl]-3-[(1E,3S)-3-methylpent-1-en-1-yl]-8H-isochromen-6-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(C(=O)C(Cl)=C2C([H])=C(OC([H])=C2[C@]1([H])C([H])([H])C(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C(\[H])=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H27ClO4/c1-6-13(3)8-9-15-10-16-17(12-27-15)18(11-19(24)14(4)7-2)22(5,26)21(25)20(16)23/h7-10,12-13,18,26H,6,11H2,1-5H3/b9-8+,14-7+/t13-,18-,22-/m0/s1

InChI Key

DIBDMIBWFDRKHK-ODXBHRCKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Chaetomium species	JEOL database	Muroga, Y., et al, Tetrahedron 65, 7580 (2009)
Mugil cephalus	LOTUS Database	35616633

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
Acyloin
Pyran
Alpha-branched alpha,beta-unsaturated-ketone
Alpha-haloketone
Alpha-chloroketone
Acryloyl-group
Enone
Tertiary alcohol
Alpha,beta-unsaturated ketone
Oxacycle
Chloroalkene
Haloalkene
Vinyl chloride
Vinyl halide
Organoheterocyclic compound
Organochloride
Hydrocarbon derivative
Alcohol
Organic oxide
Organohalogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.48	ALOGPS
logP	4.05	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.66 m³·mol⁻¹	ChemAxon
Polarizability	42.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

27024228

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44250065

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Muroga, Y., et al. (2009). Muroga, Y., et al, Tetrahedron 65, 7580 (2009). Tetrahedron.

Showing NP-Card for chaetomugilin J (NP0038550)

MOL for NP0038550 (chaetomugilin J)

3D MOL for NP0038550 (chaetomugilin J)

3D SDF for NP0038550 (chaetomugilin J)

3D-SDF for NP0038550 (chaetomugilin J)

PDB for NP0038550 (chaetomugilin J)

3D PDB for NP0038550 (chaetomugilin J)

SMILES for NP0038550 (chaetomugilin J)

INCHI for NP0038550 (chaetomugilin J)

Structure for NP0038550 (chaetomugilin J)

3D Structure for NP0038550 (chaetomugilin J)