NP-MRD: Showing NP-Card for Muridienin 2 (NP0079568)

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Record Information

Version

2.0

Created at

2022-04-29 00:35:08 UTC

Updated at

2022-04-29 00:35:08 UTC

NP-MRD ID

NP0079568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Muridienin 2

Description

Muridienin-2 belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Thus, muridienin-2 is considered to be an annonaceae acetogenin. Muridienin 2 is found in Annona muricata . Based on a literature review very few articles have been published on Muridienin-2.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202352D          

 39 39  0  0  1  0            999 V2000
   -6.1286   17.7367    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8737   16.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9932   16.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9536   17.7367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5411   15.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 39  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292202352D          

 39 39  0  0  1  0            999 V2000
   -6.1286   17.7367    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8737   16.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5411   16.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2086   16.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9932   16.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9536   17.7367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5411   15.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2556   15.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2556   14.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9701   13.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9701   13.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6845   12.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6845   11.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3990   11.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3990   10.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1135   10.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1135    9.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3990    9.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6845    9.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9701    9.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9701    8.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6845    7.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6845    6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9701    6.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2556    6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5411    6.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8267    6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1122    6.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3977    6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6832    6.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9688    6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2543    6.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5398    6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254    6.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1109    6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036    6.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3181    6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325    6.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6437   18.4041    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  1  6  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
  1 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0079568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCC\C=C/CC\C=C/CCCCCCCCCCCCC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32-33-36-34-35(2)39-37(36)38/h16-17,20-21,34-35H,3-15,18-19,22-33H2,1-2H3/b17-16-,21-20-/t35-/m0/s1

> <INCHI_KEY>
PGJOSPXBOBXUCT-GGJFXRFKSA-N

> <FORMULA>
C37H66O2

> <MOLECULAR_WEIGHT>
542.933

> <EXACT_MASS>
542.506281365

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
73.49156250519347

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-[(13Z,17Z)-dotriaconta-13,17-dien-1-yl]-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
11.02

> <JCHEM_LOGP>
14.406526404333333

> <ALOGPS_LOGS>
-7.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.470827754881434

> <JCHEM_PKA_STRONGEST_BASIC>
-6.879887748924185

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
174.88750000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
29

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.92e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-[(13Z,17Z)-dotriaconta-13,17-dien-1-yl]-5-methyl-5H-furan-2-one

> <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     -11.440  33.108   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.964  31.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.210  30.739   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.456  31.644   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -14.921  31.168   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0     -12.980  33.108   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0     -12.210  29.199   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.544  28.429   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -13.544  26.889   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.877  26.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.877  24.579   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -16.211  23.809   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -16.211  22.269   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -17.545  21.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -17.545  19.959   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -18.878  19.189   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -18.878  17.649   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -17.545  16.879   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -16.211  17.649   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.877  16.879   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.877  15.339   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -16.211  14.569   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -16.211  13.029   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -14.877  12.259   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -13.544  13.029   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.210  12.259   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.876  13.029   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.543  12.259   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.209  13.029   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.875  12.259   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.542  13.029   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.208  12.259   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.874  13.029   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.541  12.259   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.207  13.029   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.127  12.259   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.460  13.029   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.794  12.259   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -10.535  34.354   0.000  0.00  0.00           C+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    1                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₆₆O₂

Average Mass

542.9330 Da

Monoisotopic Mass

542.50628 Da

IUPAC Name

(5S)-3-[(13Z,17Z)-dotriaconta-13,17-dien-1-yl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5S)-3-[(13Z,17Z)-dotriaconta-13,17-dien-1-yl]-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC\C=C/CC\C=C/CCCCCCCCCCCCC1=C[C@H](C)OC1=O

InChI Identifier

InChI=1S/C37H66O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32-33-36-34-35(2)39-37(36)38/h16-17,20-21,34-35H,3-15,18-19,22-33H2,1-2H3/b17-16-,21-20-/t35-/m0/s1

InChI Key

PGJOSPXBOBXUCT-GGJFXRFKSA-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
Annona muricata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	11.02	ALOGPS
logP	14.41	ChemAxon
logS	-7.9	ALOGPS
pKa (Strongest Acidic)	13.47	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	174.89 m³·mol⁻¹	ChemAxon
Polarizability	73.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	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

103882676

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154497053

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Muridienin 2 (NP0079568)

MOL for NP0079568 (Muridienin 2)

3D MOL for NP0079568 (Muridienin 2)

3D SDF for NP0079568 (Muridienin 2)

3D-SDF for NP0079568 (Muridienin 2)

PDB for NP0079568 (Muridienin 2)

3D PDB for NP0079568 (Muridienin 2)

SMILES for NP0079568 (Muridienin 2)

INCHI for NP0079568 (Muridienin 2)

Structure for NP0079568 (Muridienin 2)

3D Structure for NP0079568 (Muridienin 2)