NP-MRD: Showing NP-Card for (-)-Malleastrone B (NP0076831)

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Record Information

Version

2.0

Created at

2022-04-28 22:01:12 UTC

Updated at

2022-04-28 22:01:12 UTC

NP-MRD ID

NP0076831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Malleastrone B

Description

Malleastrone B belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (-)-Malleastrone B is found in Malleastrum sp. Based on a literature review very few articles have been published on malleastrone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200012D          

 43 49  0  0  1  0            999 V2000
    3.2093   -4.2889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292200012D          

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    0.1380   -2.5803    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0633   -3.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6354   -3.8190    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4100   -4.1029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909   -1.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2140   -2.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214   -1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883   -0.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -1.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754   -1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8014   -4.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2103   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9849   -2.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1264   -3.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9011   -3.6787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933   -3.9238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4627   -4.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6692   -4.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2340   -4.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -2.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -4.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563   -5.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9808   -5.7475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176   -6.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  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
  4 11  1  0  0  0  0
 11 12  1  6  0  0  0
 10 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  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
  8 22  1  0  0  0  0
 22 23  1  6  0  0  0
  8 23  1  6  0  0  0
 20 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
  9 29  1  1  0  0  0
  5 30  1  6  0  0  0
  3 31  1  0  0  0  0
 31 32  2  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
  2 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
  1 37  1  0  0  0  0
 35 38  1  1  0  0  0
  3 39  1  6  0  0  0
  1 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@H]1[C@H](O)[C@@H]2[C@@]3(C)C=CC(=O)[C@]4(C)CO[C@@](OC(C)=O)([C@H]34)C(=O)[C@@]2(C)[C@@]23O[C@@H]2C[C@@H](C2=COC=C2)[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C33H40O10/c1-8-16(2)25(37)41-24-22(36)23-28(4)11-9-20(35)29(5)15-40-32(26(28)29,42-17(3)34)27(38)31(23,7)33-21(43-33)13-19(30(24,33)6)18-10-12-39-14-18/h9-12,14,16,19,21-24,26,36H,8,13,15H2,1-7H3/t16-,19-,21+,22+,23+,24-,26+,28+,29-,30+,31-,32+,33+/m0/s1

> <INCHI_KEY>
RDMOWPHFYJPTPP-SSZAIHIRSA-N

> <FORMULA>
C33H40O10

> <MOLECULAR_WEIGHT>
596.673

> <EXACT_MASS>
596.262147488

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
62.15855294952713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,4R,5R,6R,8R,10R,11R,13R,16S,20R)-13-(acetyloxy)-6-(furan-3-yl)-3-hydroxy-1,5,11,16-tetramethyl-12,17-dioxo-9,14-dioxahexacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{8,10}.0^{16,20}]icos-18-en-4-yl (2S)-2-methylbutanoate

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
4.294688112999999

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.840787431687488

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8443067280682164

> <JCHEM_POLAR_SURFACE_AREA>
141.87

> <JCHEM_REFRACTIVITY>
149.99

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,4R,5R,6R,8R,10R,11R,13R,16S,20R)-13-(acetyloxy)-6-(furan-3-yl)-3-hydroxy-1,5,11,16-tetramethyl-12,17-dioxo-9,14-dioxahexacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{8,10}.0^{16,20}]icos-18-en-4-yl (2S)-2-methylbutanoate

> <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       5.991  -8.006   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.942  -6.795   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.368  -5.365   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.843  -5.148   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.892  -6.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.466  -7.788   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.515  -9.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.368  -6.142   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.794  -4.712   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.745  -3.501   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.269  -3.719   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.220  -2.507   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.171  -2.072   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.122  -0.860   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.646  -1.078   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.548   0.569   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.024   0.786   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.499   1.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.925   3.209   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.258  -4.817   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.118  -6.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.186  -7.129   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.632  -7.659   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.730  -3.635   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.266  -3.739   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.840  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.658  -1.322   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.354  -2.141   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.074  -3.351   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.363  -7.805   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.859  -4.290   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.305  -4.820   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.569  -6.337   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.015  -6.867   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.387  -7.324   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.330  -8.863   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.849  -9.285   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.770  -8.002   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.000  -3.870   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.172  -9.310   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.892 -10.671   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       7.431 -10.729   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.073 -11.976   0.000  0.00  0.00           C+0
CONECT    1    2    6   37   40                                             
CONECT    2    1    3   35                                                  
CONECT    3    2    4   31   39                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8   30                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   22   23                                             
CONECT    9    8   10   20   29                                             
CONECT   10    9   11   13                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20    9   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21    8   23                                                  
CONECT   23   22    8                                                       
CONECT   24   20   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29    9                                                            
CONECT   30    5                                                            
CONECT   31    3   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2   36   38                                             
CONECT   36   35   37                                                       
CONECT   37   36    1                                                       
CONECT   38   35                                                            
CONECT   39    3                                                            
CONECT   40    1   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₀O₁₀

Average Mass

596.6730 Da

Monoisotopic Mass

596.26215 Da

IUPAC Name

(1R,2R,3R,4R,5R,6R,8R,10R,11R,13R,16S,20R)-13-(acetyloxy)-6-(furan-3-yl)-3-hydroxy-1,5,11,16-tetramethyl-12,17-dioxo-9,14-dioxahexacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{8,10}.0^{16,20}]icos-18-en-4-yl (2S)-2-methylbutanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@H]1[C@H](O)[C@@H]2[C@@]3(C)C=CC(=O)[C@]4(C)CO[C@@](OC(C)=O)([C@H]34)C(=O)[C@@]2(C)[C@@]23O[C@@H]2C[C@@H](C2=COC=C2)[C@]13C

InChI Identifier

InChI=1S/C33H40O10/c1-8-16(2)25(37)41-24-22(36)23-28(4)11-9-20(35)29(5)15-40-32(26(28)29,42-17(3)34)27(38)31(23,7)33-21(43-33)13-19(30(24,33)6)18-10-12-39-14-18/h9-12,14,16,19,21-24,26,36H,8,13,15H2,1-7H3/t16-,19-,21+,22+,23+,24-,26+,28+,29-,30+,31-,32+,33+/m0/s1

InChI Key

RDMOWPHFYJPTPP-SSZAIHIRSA-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
Malleastrum sp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
17-furanylsteroid skeleton
Steroid ester
3-oxo-delta-1-steroid
Delta-1-steroid
Steroid
Naphthopyran
Naphthofuran
Naphthalene
Alpha-acyloxy ketone
Ketal
Fatty acid ester
Cyclohexenone
Fatty acyl
Dicarboxylic acid or derivatives
Pyran
Oxane
Tetrahydrofuran
Cyclic alcohol
Heteroaromatic compound
Furan
Ketone
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Dialkyl ether
Oxacycle
Oxirane
Ether
Organic oxygen compound
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
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	3.59	ALOGPS
logP	4.29	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	141.87 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	149.99 m³·mol⁻¹	ChemAxon
Polarizability	62.16 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039718

Chemspider ID

23314637

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24854445

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Malleastrone B (NP0076831)

MOL for NP0076831 ((-)-Malleastrone B)

3D MOL for NP0076831 ((-)-Malleastrone B)

3D SDF for NP0076831 ((-)-Malleastrone B)

3D-SDF for NP0076831 ((-)-Malleastrone B)

PDB for NP0076831 ((-)-Malleastrone B)

3D PDB for NP0076831 ((-)-Malleastrone B)

SMILES for NP0076831 ((-)-Malleastrone B)

INCHI for NP0076831 ((-)-Malleastrone B)

Structure for NP0076831 ((-)-Malleastrone B)

3D Structure for NP0076831 ((-)-Malleastrone B)