NP-MRD: Showing NP-Card for (1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione (NP0160259)

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Record Information

Version

2.0

Created at

2022-09-02 18:10:14 UTC

Updated at

2022-09-02 18:10:14 UTC

NP-MRD ID

NP0160259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione

Description

Chloctanspirone B 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. (1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione is found in Penicillium solitum. Based on a literature review very few articles have been published on Chloctanspirone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220102D          

 29 31  0  0  1  0            999 V2000
   -3.2215    1.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352    1.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583    0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720    0.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2951   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5088   -0.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3319   -1.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    0.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8626    0.9531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331    1.2596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3562    2.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853    0.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9033    0.2146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9564    1.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8124    1.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9588    1.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085    1.9642    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5149    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2652   -0.2179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8213   -0.8273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4594   -0.3948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2097   -1.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869   -0.3521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4963    0.2040    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9381   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247    0.7386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3194    1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288    1.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  4  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  1  0  0  0
 14 24  1  0  0  0  0
 24  8  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  1  0  0  0
 25 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    7.2780   -0.8267    1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8759   -0.5342    1.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9304   -0.4786    1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278   -0.1965    1.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903   -0.1444    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2037    0.1272    0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8833    0.3398    2.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2684    0.1833   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4014   -0.0051   -1.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544   -0.4735   -2.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    0.4445   -2.2993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5795    0.4445   -3.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8725   -0.5887   -1.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9852   -0.5831   -0.3723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4823   -1.8942    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5460   -2.5324   -0.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164   -2.4292    1.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4706   -3.9342    2.0730 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1303   -1.8301    1.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995   -0.5729    1.4539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0914   -0.5257    1.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4552   -0.5563   -0.0382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1669    0.4105   -0.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1770    0.4760    0.2936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4190    1.8682   -0.2884 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3425    2.8133    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6261    2.3999    0.0650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1748    1.7644   -1.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644    2.7231   -2.4545 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2740   -1.3728    0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8028   -1.4842    2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8593    0.0929    1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6471   -0.3742    3.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1681   -0.6396    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -0.0300    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -0.3178   -0.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8963   -0.4503    2.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695    0.0210   -4.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745    1.5106   -4.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3352   -0.1417   -3.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582   -1.5664   -2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -0.3700   -2.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -2.2718    2.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2195    0.2941    1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4246    0.1960    1.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8575   -1.5497   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6127    0.0663   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2808    0.4270    1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6102    2.6903   -0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331    3.8410    0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2319    2.7253    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5309    2.8152    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  6
 25 28  1  0
 28 29  2  0
 28 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 15  1  0
 15 16  2  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
 14 24  1  0
 14 15  1  1
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  7 37  1  0
 24 48  1  1
 26 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 22 46  1  6
 23 47  1  0
 20 44  1  1
 21 45  1  0
 19 43  1  0
M  END


  Mrv1652309022220102D          

 29 31  0  0  1  0            999 V2000
   -3.2215    1.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352    1.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583    0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720    0.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2951   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5088   -0.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3319   -1.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006   -0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    0.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8626    0.9531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331    1.2596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3562    2.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853    0.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9033    0.2146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9564    1.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8124    1.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9588    1.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085    1.9642    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5149    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2652   -0.2179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8213   -0.8273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4594   -0.3948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2097   -1.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869   -0.3521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4963    0.2040    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9381   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247    0.7386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3194    1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288    1.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  4  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  1  0  0  0
 14 24  1  0  0  0  0
 24  8  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  1  0  0  0
 25 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0160259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C=C\C(O)=C1[C@H]2[C@](C)(O)C(=O)[C@](C)(C[C@]22[C@H](O)[C@@H](O)C=C(Cl)C2=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H23ClO7/c1-4-5-6-7-11(23)13-14-20(3,29)18(28)19(2,17(13)27)9-21(14)15(25)10(22)8-12(24)16(21)26/h4-8,12,14,16,23-24,26,29H,9H2,1-3H3/b5-4+,7-6+,13-11?/t12-,14-,16+,19+,20-,21-/m0/s1

> <INCHI_KEY>
PHXAMGFMNFACCT-AICNVHPQSA-N

> <FORMULA>
C21H23ClO7

> <MOLECULAR_WEIGHT>
422.86

> <EXACT_MASS>
422.1132308

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.97240575625469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,5'S,6S,6'S)-3'-chloro-5',6,6'-trihydroxy-7-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.631117004

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.820901086631153

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.028633109642174

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3748520015416856

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
109.79719999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5'S,6S,6'S)-3'-chloro-5',6,6'-trihydroxy-7-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.014   3.177   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.546   2.711   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.216   1.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.748   0.741   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.418  -0.763   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.950  -1.229   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.620  -2.733   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.188  -0.191   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.142   1.313   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.610   1.779   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.995   2.351   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.665   3.855   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.466   1.403   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.686   0.401   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.785   2.103   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.516   3.271   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.656   2.199   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       4.122   3.666   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       4.694   1.061   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.228  -0.407   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.266  -1.544   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.724  -0.737   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.258  -2.205   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.656  -0.657   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.793   0.381   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.618  -0.920   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.966   1.379   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.463   1.885   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.600   2.923   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   24                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   28                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   22   24                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14   23                                                  
CONECT   23   22                                                            
CONECT   24   14    8   25                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   11   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₃ClO₇

Average Mass

422.8600 Da

Monoisotopic Mass

422.11323 Da

IUPAC Name

(1S,2R,4R,5'S,6S,6'S)-3'-chloro-5',6,6'-trihydroxy-7-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione

Traditional Name

(1S,2R,4R,5'S,6S,6'S)-3'-chloro-5',6,6'-trihydroxy-7-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione

CAS Registry Number

Not Available

SMILES

C\C=C\C=C\C(O)=C1[C@H]2[C@](C)(O)C(=O)[C@](C)(C[C@]22[C@H](O)[C@@H](O)C=C(Cl)C2=O)C1=O

InChI Identifier

InChI=1S/C21H23ClO7/c1-4-5-6-7-11(23)13-14-20(3,29)18(28)19(2,17(13)27)9-21(14)15(25)10(22)8-12(24)16(21)26/h4-8,12,14,16,23-24,26,29H,9H2,1-3H3/b5-4+,7-6+,13-11?/t12-,14-,16+,19+,20-,21-/m0/s1

InChI Key

PHXAMGFMNFACCT-AICNVHPQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 solitum	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
Alpha-haloketone
Alpha-chloroketone
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Polyol
Enol
Organic oxide
Hydrocarbon derivative
Organochloride
Organohalogen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.38	ALOGPS
logP	1.63	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.8 m³·mol⁻¹	ChemAxon
Polarizability	40.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436876

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584564

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione (NP0160259)

MOL for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)

3D MOL for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)

3D SDF for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)

3D-SDF for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)

PDB for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)

3D PDB for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)

SMILES for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)

INCHI for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)

Structure for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)

3D Structure for NP0160259 ((1s,2r,4r,5's,6s,6's)-3'-chloro-5',6,6'-trihydroxy-7-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione)