NP-MRD: Showing NP-Card for (+)-Shizukaol J (NP0077166)

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Record Information

Version

2.0

Created at

2022-04-28 22:19:01 UTC

Updated at

2022-04-28 22:19:02 UTC

NP-MRD ID

NP0077166

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Shizukaol J

Description

Shizukaol J belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (+)-Shizukaol J is found in Chloranthus fortunei and Chloranthus japonicus. (+)-Shizukaol J was first documented in 2022 (PMID: 35102682). Based on a literature review a small amount of articles have been published on Shizukaol J.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200192D          

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M  END

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M  END


  Mrv1652304292200192D          

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    4.8964   -0.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9360    0.5769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2863   -0.7341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5986   -1.4977    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1038   -0.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575   -0.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1313   -2.4689    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
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  2  0  0  0  0
  8 11  1  1  0  0  0
  7 12  1  1  0  0  0
  6 13  1  1  0  0  0
  5 13  1  1  0  0  0
  4 14  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 24 35  1  1  0  0  0
 23 36  1  0  0  0  0
 36 37  1  0  0  0  0
 21 37  1  0  0  0  0
 37 38  1  1  0  0  0
 36 38  1  1  0  0  0
 23 39  1  1  0  0  0
 15 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0077166

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)C1=CC2=C(C[C@@](C)(C(=O)OC)C3=CC4=C(C)[C@H]5C[C@H]5[C@]4(C)[C@@H](O)C3=O)[C@H]3C[C@H]3[C@]2(C)[C@@H](O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H36O8/c1-13-15-8-20(15)31(4)19(13)11-23(25(34)27(31)36)30(3,29(38)40-7)12-18-17-10-21(17)32(5)22(18)9-16(24(33)26(32)35)14(2)28(37)39-6/h9,11,15,17,20-21,26-27,35-36H,2,8,10,12H2,1,3-7H3/t15-,17-,20-,21-,26+,27+,30-,31-,32+/m1/s1

> <INCHI_KEY>
UPYQSOJNCPYAPV-UJWILHQTSA-N

> <FORMULA>
C32H36O8

> <MOLECULAR_WEIGHT>
548.632

> <EXACT_MASS>
548.241018119

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
58.10829296955542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1aR,1bS,2R,6aS)-6-[(2R)-2-[(1aR,1bS,2R,6aS)-2-hydroxy-1b,6-dimethyl-3-oxo-1H,1aH,1bH,2H,3H,6aH-cyclopropa[a]inden-4-yl]-3-methoxy-2-methyl-3-oxopropyl]-2-hydroxy-1b-methyl-3-oxo-1H,1aH,1bH,2H,3H,6aH-cyclopropa[a]inden-4-yl]prop-2-enoate

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.465515453999999

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.165540967691946

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.563358922581692

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7297049807520635

> <JCHEM_POLAR_SURFACE_AREA>
127.19999999999999

> <JCHEM_REFRACTIVITY>
147.5874

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(1aR,1bS,2R,6aS)-6-[(2R)-2-[(1aR,1bS,2R,6aS)-2-hydroxy-1b,6-dimethyl-3-oxo-1H,1aH,2H,6aH-cyclopropa[a]inden-4-yl]-3-methoxy-2-methyl-3-oxopropyl]-2-hydroxy-1b-methyl-3-oxo-1H,1aH,2H,6aH-cyclopropa[a]inden-4-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -2.829  -6.665   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.943  -8.201   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.330  -8.870   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.761 -10.349   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.300 -10.396   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.821  -8.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.603  -8.004   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.490  -6.468   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.103  -5.798   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.989  -4.263   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -6.763  -5.601   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.960  -7.275   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.816 -10.122   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.818 -11.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.443  -5.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.773  -7.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.763  -7.496   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.640  -8.656   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.970 -10.043   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.056  -5.326   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.058  -3.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.368  -2.980   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.001  -1.484   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.114  -0.419   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.592  -0.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.704   0.216   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.958  -2.345   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.846  -3.411   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.437  -2.776   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.803  -4.272   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.549  -1.711   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.183  -0.215   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.028  -2.142   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.140  -1.076   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.747   1.077   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.534  -1.370   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.117  -2.796   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.060  -1.578   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.481  -0.035   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.112  -4.609   0.000  0.00  0.00           C+0
CONECT    1    2    9   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    3    8   12                                             
CONECT    8    7    9   11                                                  
CONECT    9    8    1   10                                                  
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    7                                                            
CONECT   13    6    5                                                       
CONECT   14    4                                                            
CONECT   15    1   16   20   40                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   37                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24   36   39                                             
CONECT   24   23   25   35                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   22                                                       
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   24                                                            
CONECT   36   23   37   38                                                  
CONECT   37   36   21   38                                                  
CONECT   38   37   36                                                       
CONECT   39   23                                                            
CONECT   40   15                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₆O₈

Average Mass

548.6320 Da

Monoisotopic Mass

548.24102 Da

IUPAC Name

methyl 2-[(1aR,1bS,2R,6aS)-6-[(2R)-2-[(1aR,1bS,2R,6aS)-2-hydroxy-1b,6-dimethyl-3-oxo-1H,1aH,1bH,2H,3H,6aH-cyclopropa[a]inden-4-yl]-3-methoxy-2-methyl-3-oxopropyl]-2-hydroxy-1b-methyl-3-oxo-1H,1aH,1bH,2H,3H,6aH-cyclopropa[a]inden-4-yl]prop-2-enoate

Traditional Name

methyl 2-[(1aR,1bS,2R,6aS)-6-[(2R)-2-[(1aR,1bS,2R,6aS)-2-hydroxy-1b,6-dimethyl-3-oxo-1H,1aH,2H,6aH-cyclopropa[a]inden-4-yl]-3-methoxy-2-methyl-3-oxopropyl]-2-hydroxy-1b-methyl-3-oxo-1H,1aH,2H,6aH-cyclopropa[a]inden-4-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)C1=CC2=C(C[C@@](C)(C(=O)OC)C3=CC4=C(C)[C@H]5C[C@H]5[C@]4(C)[C@@H](O)C3=O)[C@H]3C[C@H]3[C@]2(C)[C@@H](O)C1=O

InChI Identifier

InChI=1S/C32H36O8/c1-13-15-8-20(15)31(4)19(13)11-23(25(34)27(31)36)30(3,29(38)40-7)12-18-17-10-21(17)32(5)22(18)9-16(24(33)26(32)35)14(2)28(37)39-6/h9,11,15,17,20-21,26-27,35-36H,2,8,10,12H2,1,3-7H3/t15-,17-,20-,21-,26+,27+,30-,31-,32+/m1/s1

InChI Key

UPYQSOJNCPYAPV-UJWILHQTSA-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 fortunei	Plant	KNApSAcK
Chloranthus japonicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Bisabolane sesquiterpenoid
Fatty acid ester
Cyclohexenone
Dicarboxylic acid or derivatives
Fatty acyl
Enoate ester
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
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	2.93	ALOGPS
logP	2.47	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.56	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	8	ChemAxon
Refractivity	147.59 m³·mol⁻¹	ChemAxon
Polarizability	58.11 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040298

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

101938873

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang X, Wang Z, Ma X, Huang Z, Sun K, Gao X, Fu S, Liu B: Asymmetric Total Synthesis of Shizukaol J, Trichloranoid C and Trishizukaol A. Angew Chem Int Ed Engl. 2022 Apr 19;61(17):e202200258. doi: 10.1002/anie.202200258. Epub 2022 Feb 28. [PubMed:35102682 ]

Showing NP-Card for (+)-Shizukaol J (NP0077166)

MOL for NP0077166 ((+)-Shizukaol J)

3D MOL for NP0077166 ((+)-Shizukaol J)

3D SDF for NP0077166 ((+)-Shizukaol J)

3D-SDF for NP0077166 ((+)-Shizukaol J)

PDB for NP0077166 ((+)-Shizukaol J)

3D PDB for NP0077166 ((+)-Shizukaol J)

SMILES for NP0077166 ((+)-Shizukaol J)

INCHI for NP0077166 ((+)-Shizukaol J)

Structure for NP0077166 ((+)-Shizukaol J)

3D Structure for NP0077166 ((+)-Shizukaol J)