NP-MRD: Showing NP-Card for (+)-Sampsonione N (NP0077098)

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Record Information

Version

2.0

Created at

2022-04-28 22:15:53 UTC

Updated at

2022-04-28 22:15:53 UTC

NP-MRD ID

NP0077098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Sampsonione N

Description

Sampsonione N belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. (+)-Sampsonione N is found in Hypericum sampsonii. Based on a literature review very few articles have been published on Sampsonione N.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200152D          

 38 41  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652304292200152D          

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   -0.8063    0.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4124    0.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308   -0.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -1.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4431   -0.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  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  1  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  8 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
  3 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  1 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@@H]1C[C@]2(CC=C(C)C)C(=O)C3=C(O[C@H](C3)C(C)(C)O)[C@@](C(=O)C3=CC=CC=C3)(C2=O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O5/c1-20(2)14-15-23-19-32(17-16-21(3)4)27(35)24-18-25(31(7,8)37)38-28(24)33(29(32)36,30(23,5)6)26(34)22-12-10-9-11-13-22/h9-14,16,23,25,37H,15,17-19H2,1-8H3/t23-,25-,32-,33+/m1/s1

> <INCHI_KEY>
ZWTGJCOSOVVWJL-XXASJIQDSA-N

> <FORMULA>
C33H42O5

> <MOLECULAR_WEIGHT>
518.694

> <EXACT_MASS>
518.303224452

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
58.27591723904089

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,8R,10R)-1-benzoyl-4-(2-hydroxypropan-2-yl)-11,11-dimethyl-8,10-bis(3-methylbut-2-en-1-yl)-3-oxatricyclo[6.3.1.0^{2,6}]dodec-2(6)-ene-7,12-dione

> <ALOGPS_LOGP>
5.34

> <JCHEM_LOGP>
6.6787013443333345

> <ALOGPS_LOGS>
-5.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.297349489093332

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1061393334705754

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
152.78200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.56e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,8R,10R)-1-benzoyl-4-(2-hydroxypropan-2-yl)-11,11-dimethyl-8,10-bis(3-methylbut-2-en-1-yl)-3-oxatricyclo[6.3.1.0^{2,6}]dodec-2(6)-ene-7,12-dione

> <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      -0.035   0.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.105  -0.773   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.289  -1.759   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.822  -1.619   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.539  -2.982   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.808  -0.435   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.668   1.099   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.484   2.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.951   1.944   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.911   3.483   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.295   2.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.942   3.554   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.897   4.686   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.444   3.893   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.902   5.364   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.404   5.703   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.449   4.571   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.991   3.101   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.489   2.762   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.406   0.312   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.486   1.547   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.083   1.706   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.098   0.547   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.310  -0.776   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.631   0.687   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.165   0.827   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.772  -0.846   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.491   2.221   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.831  -3.229   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.671  -3.568   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.128  -5.039   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.084  -6.170   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.631  -5.378   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.505   1.218   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.637   0.173   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.298  -1.329   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.429  -2.374   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.827  -1.787   0.000  0.00  0.00           C+0
CONECT    1    2    9   34                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20   29                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   24                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   12   20                                             
CONECT    9    8    1   10   11                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    8    3   21                                                  
CONECT   21   20                                                            
CONECT   22    7   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23    6                                                       
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29    3   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    1   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₂O₅

Average Mass

518.6940 Da

Monoisotopic Mass

518.30322 Da

IUPAC Name

(1S,4R,8R,10R)-1-benzoyl-4-(2-hydroxypropan-2-yl)-11,11-dimethyl-8,10-bis(3-methylbut-2-en-1-yl)-3-oxatricyclo[6.3.1.0^{2,6}]dodec-2(6)-ene-7,12-dione

Traditional Name

(1S,4R,8R,10R)-1-benzoyl-4-(2-hydroxypropan-2-yl)-11,11-dimethyl-8,10-bis(3-methylbut-2-en-1-yl)-3-oxatricyclo[6.3.1.0^{2,6}]dodec-2(6)-ene-7,12-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@@H]1C[C@]2(CC=C(C)C)C(=O)C3=C(O[C@H](C3)C(C)(C)O)[C@@](C(=O)C3=CC=CC=C3)(C2=O)C1(C)C

InChI Identifier

InChI=1S/C33H42O5/c1-20(2)14-15-23-19-32(17-16-21(3)4)27(35)24-18-25(31(7,8)37)38-28(24)33(29(32)36,30(23,5)6)26(34)22-12-10-9-11-13-22/h9-14,16,23,25,37H,15,17-19H2,1-8H3/t23-,25-,32-,33+/m1/s1

InChI Key

ZWTGJCOSOVVWJL-XXASJIQDSA-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
Hypericum sampsonii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Aromatic monoterpenoid
Monoterpenoid
Benzoyl
Aryl alkyl ketone
Cyclohexenone
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Dihydrofuran
Vinylogous ester
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	5.34	ALOGPS
logP	6.68	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	152.78 m³·mol⁻¹	ChemAxon
Polarizability	58.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

C00040207

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

101451478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Sampsonione N (NP0077098)

MOL for NP0077098 ((+)-Sampsonione N)

3D MOL for NP0077098 ((+)-Sampsonione N)

3D SDF for NP0077098 ((+)-Sampsonione N)

3D-SDF for NP0077098 ((+)-Sampsonione N)

PDB for NP0077098 ((+)-Sampsonione N)

3D PDB for NP0077098 ((+)-Sampsonione N)

SMILES for NP0077098 ((+)-Sampsonione N)

INCHI for NP0077098 ((+)-Sampsonione N)

Structure for NP0077098 ((+)-Sampsonione N)

3D Structure for NP0077098 ((+)-Sampsonione N)