NP-MRD: Showing NP-Card for Cycloshizukaol A (NP0076387)

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Record Information

Version

2.0

Created at

2022-04-28 21:31:32 UTC

Updated at

2022-04-28 21:31:32 UTC

NP-MRD ID

NP0076387

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cycloshizukaol A

Description

2,12-Dimethyl (2S,5R,7S,8R,12S,15R,17S,18S,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2⁸,¹¹.0⁴,⁹.0⁵,⁷.0¹⁵,¹⁷.0¹⁸,²²]Tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate 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. Cycloshizukaol A is found in Chloranthus japonicus. Based on a literature review very few articles have been published on 2,12-dimethyl (2S,5R,7S,8R,12S,15R,17S,18S,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2⁸,¹¹.0⁴,⁹.0⁵,⁷.0¹⁵,¹⁷.0¹⁸,²²]Tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223312D          

 40 46  0  0  1  0            999 V2000
    6.9312    0.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9993   -2.5204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1745   -2.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -1.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0180   -0.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5677    1.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7572    1.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395    1.9433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008    2.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
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  6  7  1  0  0  0  0
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  6 31  1  1  0  0  0
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 33 40  1  1  0  0  0
 32 40  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282223312D          

 40 46  0  0  1  0            999 V2000
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    8.3485   -2.9911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2663   -3.9242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8050   -4.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8812   -3.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9123   -1.3203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1420   -0.5279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4593   -0.0647    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3468    0.7526    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5828    1.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4703    1.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9984    1.2587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1602    0.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7134   -1.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  1  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  1  0  0  0
 20 25  1  1  0  0  0
 19 26  1  1  0  0  0
 18 26  1  1  0  0  0
  6 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 31  1  1  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
  1 36  1  0  0  0  0
 36 37  2  0  0  0  0
 35 38  1  1  0  0  0
 34 39  1  6  0  0  0
 33 40  1  1  0  0  0
 32 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0076387

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)CC2=C3C=C(C(=O)[C@@H](O)[C@]3(C)[C@H]3C[C@@H]23)[C@](C)(CC2=C3C=C1C(=O)[C@@H](O)[C@@]3(C)[C@H]1C[C@@H]21)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H36O8/c1-29(27(37)39-5)11-15-13-7-17(13)32(4)20(15)10-22(24(34)26(32)36)30(2,28(38)40-6)12-16-14-8-18(14)31(3)19(16)9-21(29)23(33)25(31)35/h9-10,13-14,17-18,25-26,35-36H,7-8,11-12H2,1-6H3/t13-,14-,17-,18-,25+,26+,29-,30-,31-,32+/m0/s1

> <INCHI_KEY>
YSPXFYFVBVEVBW-QGGXRMNDSA-N

> <FORMULA>
C32H36O8

> <MOLECULAR_WEIGHT>
548.632

> <EXACT_MASS>
548.241018119

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.97001233357386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,12-dimethyl (2S,5R,7S,8R,12S,15R,17S,18S,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2^{8,11}.0^{4,9}.0^{5,7}.0^{15,17}.0^{18,22}]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
1.9715804840000004

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.172742485300677

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.570682493952372

> <JCHEM_PKA_STRONGEST_BASIC>
-3.729712957041806

> <JCHEM_POLAR_SURFACE_AREA>
127.20000000000003

> <JCHEM_REFRACTIVITY>
145.8818

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,12-dimethyl (2S,5R,7S,8R,12S,15R,17S,18S,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2^{8,11}.0^{4,9}.0^{5,7}.0^{15,17}.0^{18,22}]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      12.938   1.041   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.148  -0.484   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.575  -1.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.097  -2.514   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.382  -3.905   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.065  -4.705   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.526  -4.739   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.316  -3.213   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.890  -2.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.367  -1.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.082   0.208   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.399   1.007   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.393   2.173   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.880   1.886   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.900   3.628   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.895   4.794   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.619   2.531   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.828  -1.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.399  -2.712   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.673  -3.577   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.883  -5.103   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.310  -5.683   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.520  -7.209   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.667  -6.047   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.365  -4.389   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.332  -1.601   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.071  -5.871   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.584  -5.583   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.564  -7.325   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.569  -8.492   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.845  -6.229   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.636  -2.465   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.065  -0.986   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.791  -0.121   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.581   1.405   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.155   1.986   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      13.945   3.511   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      16.797   2.350   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      17.099   0.692   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      18.132  -2.096   0.000  0.00  0.00           C+0
CONECT    1    2   12   36                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   27   31                                             
CONECT    7    6    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11    1   13   17                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12                                                            
CONECT   18   10   19   26                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19    9   21   25                                             
CONECT   21   20   22   24                                                  
CONECT   22   21    7   23                                                  
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   20                                                            
CONECT   26   19   18                                                       
CONECT   27    6   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31    6                                                            
CONECT   32    4   33   40                                                  
CONECT   33   32   34   40                                                  
CONECT   34   33    3   35   39                                             
CONECT   35   34   36   38                                                  
CONECT   36   35    1   37                                                  
CONECT   37   36                                                            
CONECT   38   35                                                            
CONECT   39   34                                                            
CONECT   40   33   32                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Value	Source
2,12-Dimethyl (2S,5R,7S,8R,12S,15R,17S,18S,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2,.0,.0,.0,.0,]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylic acid	Generator

Chemical Formula

C₃₂H₃₆O₈

Average Mass

548.6320 Da

Monoisotopic Mass

548.24102 Da

IUPAC Name

2,12-dimethyl (2S,5R,7S,8R,12S,15R,17S,18S,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2^{8,11}.0^{4,9}.0^{5,7}.0^{15,17}.0^{18,22}]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)CC2=C3C=C(C(=O)[C@@H](O)[C@]3(C)[C@H]3C[C@@H]23)[C@](C)(CC2=C3C=C1C(=O)[C@@H](O)[C@@]3(C)[C@H]1C[C@@H]21)C(=O)OC

InChI Identifier

InChI=1S/C32H36O8/c1-29(27(37)39-5)11-15-13-7-17(13)32(4)20(15)10-22(24(34)26(32)36)30(2,28(38)40-6)12-16-14-8-18(14)31(3)19(16)9-21(29)23(33)25(31)35/h9-10,13-14,17-18,25-26,35-36H,7-8,11-12H2,1-6H3/t13-,14-,17-,18-,25+,26+,29-,30-,31-,32+/m0/s1

InChI Key

YSPXFYFVBVEVBW-QGGXRMNDSA-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
Chloranthus japonicus	Plant	KNApSAcK

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
Dicarboxylic acid or derivatives
Methyl ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	2.47	ALOGPS
logP	1.97	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	145.88 m³·mol⁻¹	ChemAxon
Polarizability	56.97 Å³	ChemAxon
Number of Rings	7	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162822741

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cycloshizukaol A (NP0076387)

MOL for NP0076387 (Cycloshizukaol A)

3D MOL for NP0076387 (Cycloshizukaol A)

3D SDF for NP0076387 (Cycloshizukaol A)

3D-SDF for NP0076387 (Cycloshizukaol A)

PDB for NP0076387 (Cycloshizukaol A)

3D PDB for NP0076387 (Cycloshizukaol A)

SMILES for NP0076387 (Cycloshizukaol A)

INCHI for NP0076387 (Cycloshizukaol A)

Structure for NP0076387 (Cycloshizukaol A)

3D Structure for NP0076387 (Cycloshizukaol A)