NP-MRD: Showing NP-Card for schiprolactone a (NP0213906)

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Record Information

Version

2.0

Created at

2022-09-05 13:02:57 UTC

Updated at

2022-09-05 13:02:57 UTC

NP-MRD ID

NP0213906

Secondary Accession Numbers

None

Natural Product Identification

Common Name

schiprolactone a

Description

Schiprolactone A belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Schiprolactone A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. schiprolactone a is found in Schisandra propinqua. schiprolactone a was first documented in 2003 (PMID: 14661856). Based on a literature review very few articles have been published on schiprolactone A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215022D          

 38 43  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309052215022D          

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    4.0217   -6.2095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6092   -6.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0217   -7.6384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7842   -6.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717   -6.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7842   -5.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628   -6.2095    0.0000 C   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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  6  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 15  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  7 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  6  0  0  0
 31  5  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  0  0  0  0
 35 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213906

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@](C)([C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)C=C1C=CC(=O)OC(C)(C)[C@@H]1CC3)[C@@H]1OC(=O)C2CC1C2

> <INCHI_IDENTIFIER>
InChI=1S/C32H42O6/c1-18(33)37-32(6,27-21-16-22(17-21)28(35)36-27)25-12-14-30(4)24-9-8-23-19(7-10-26(34)38-29(23,2)3)15-20(24)11-13-31(25,30)5/h7,10,15,21-23,25,27H,8-9,11-14,16-17H2,1-6H3/t21?,22?,23-,25+,27-,30+,31-,32+/m1/s1

> <INCHI_KEY>
XVPNHPJRBZKAFN-ABHCLWBLSA-N

> <FORMULA>
C32H42O6

> <MOLECULAR_WEIGHT>
522.682

> <EXACT_MASS>
522.298139072

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
58.725680703314545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-1-[(2R)-4-oxo-3-oxabicyclo[3.1.1]heptan-2-yl]-1-[(9R,13R,16S,17R)-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0^{3,9}.0^{13,17}]nonadeca-1(12),2,4-trien-16-yl]ethyl acetate

> <JCHEM_LOGP>
4.980367186999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.4838768027300375

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
144.57139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-1-[(2R)-4-oxo-3-oxabicyclo[3.1.1]heptan-2-yl]-1-[(9R,13R,16S,17R)-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0^{3,9}.0^{13,17}]nonadeca-1(12),2,4-trien-16-yl]ethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.967  -6.256   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.507  -6.256   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.277  -4.923   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.277  -7.590   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.507  -8.924   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.173  -8.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.841  -9.694   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.002 -11.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.508 -11.545   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.278 -10.212   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.183 -11.458   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.784  -9.892   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.260  -8.427   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.702  -7.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.024  -8.676   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.088  -7.563   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.622  -7.701   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.471  -8.986   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      20.997  -8.779   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      18.995 -10.450   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.553 -10.992   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.401 -12.277   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.489 -12.105   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.231 -10.202   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.167 -11.315   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.633 -11.177   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.230  -7.282   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.724  -7.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.248  -9.067   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.103  -8.037   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.737 -10.257   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.507 -11.591   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.737 -12.925   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.507 -14.258   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.197 -12.925   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.427 -11.591   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.197 -10.257   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.531 -11.591   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   31                                             
CONECT    6    5                                                            
CONECT    7    5    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   29                                             
CONECT   11   10                                                            
CONECT   12   10   13   26                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   15   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   12                                                       
CONECT   27   13   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    7   10   30                                             
CONECT   30   29                                                            
CONECT   31    5   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36   31   38                                                  
CONECT   38   37   35                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₂O₆

Average Mass

522.6820 Da

Monoisotopic Mass

522.29814 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@](C)([C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)C=C1C=CC(=O)OC(C)(C)[C@@H]1CC3)[C@@H]1OC(=O)C2CC1C2

InChI Identifier

InChI=1S/C32H42O6/c1-18(33)37-32(6,27-21-16-22(17-21)28(35)36-27)25-12-14-30(4)24-9-8-23-19(7-10-26(34)38-29(23,2)3)15-20(24)11-13-31(25,30)5/h7,10,15,21-23,25,27H,8-9,11-14,16-17H2,1-6H3/t21?,22?,23-,25+,27-,30+,31-,32+/m1/s1

InChI Key

XVPNHPJRBZKAFN-ABHCLWBLSA-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
Schisandra propinqua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

acetate ester (CHEBI:66430 )
lactone (CHEBI:66430 )
tetracyclic triterpenoid (CHEBI:66430 )

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

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

28639004

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70697836

PDB ID

Not Available

ChEBI ID

66430

Good Scents ID

Not Available

References

General References

Chen YG, Wu ZC, Lv YP, Gui SH, Wen J, Liao XR, Yuan LM, Halaweish F: Triterpenoids from Schisandra henryi with cytotoxic effect on leukemia and Hela cells in vitro. Arch Pharm Res. 2003 Nov;26(11):912-6. doi: 10.1007/BF02980199. [PubMed:14661856 ]
LOTUS database [Link]

Showing NP-Card for schiprolactone a (NP0213906)

MOL for NP0213906 (schiprolactone a)

3D MOL for NP0213906 (schiprolactone a)

3D SDF for NP0213906 (schiprolactone a)

3D-SDF for NP0213906 (schiprolactone a)

PDB for NP0213906 (schiprolactone a)

3D PDB for NP0213906 (schiprolactone a)

SMILES for NP0213906 (schiprolactone a)

INCHI for NP0213906 (schiprolactone a)

Structure for NP0213906 (schiprolactone a)

3D Structure for NP0213906 (schiprolactone a)