NP-MRD: Showing NP-Card for Arisugacin A (NP0023255)

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Record Information

Version

2.0

Created at

2021-01-06 08:21:49 UTC

Updated at

2021-07-15 17:41:15 UTC

NP-MRD ID

NP0023255

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arisugacin A

Provided By

NPAtlas

Description

Arisugacin 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. Arisugacin A is found in Penicillium. Arisugacin A was first documented in 2002 (PMID: 11820881). Based on a literature review a small amount of articles have been published on Arisugacin A (PMID: 26159481) (PMID: 21216144).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105403D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242105403D          

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 36 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023255

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12C([H])([H])C([H])([H])[C@]3(OC4=C(C(=O)OC(=C4[H])C4=C([H])C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C4[H])C([H])([H])[C@]3(O[H])[C@]1(C(=O)C([H])=C([H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O8/c1-24(2)10-9-22(29)26(4)27(24,31)12-11-25(3)28(26,32)15-17-20(36-25)14-19(35-23(17)30)16-7-8-18(33-5)21(13-16)34-6/h7-10,13-14,31-32H,11-12,15H2,1-6H3/t25-,26+,27-,28-/m1/s1

> <INCHI_KEY>
MIHBCQWIBJDVPX-JUDWXZBOSA-N

> <FORMULA>
C28H32O8

> <MOLECULAR_WEIGHT>
496.556

> <EXACT_MASS>
496.20971799

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.909774054961204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5aR,7aR,11aS,11bS)-3-(3,4-dimethoxyphenyl)-7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-1,5a,6,7,7a,8,11,11a,11b,12-decahydro-2,5-dioxatetraphene-1,11-dione

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
2.662746489666666

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.871524456863

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.890721426109053

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3658431139009384

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000002

> <JCHEM_REFRACTIVITY>
133.87990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,7aR,11aS,11bS)-3-(3,4-dimethoxyphenyl)-7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-7,12-dihydro-6H-2,5-dioxatetraphene-1,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
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  1  2  1  0
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 23 24  1  1
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 30 31  1  1
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  6 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
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 13  7  1  0
 30 15  1  0
 32  9  1  0
 26 17  1  0
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 31 63  1  0
 31 64  1  0
 33 65  1  0
 36 66  1  0
 36 67  1  0
 36 68  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       8.959  -2.683  -1.569  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.614  -1.700  -0.601  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.283  -1.337  -0.486  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.303  -1.896  -1.273  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.965  -1.501  -1.125  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.619  -0.562  -0.203  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.219  -0.116  -0.015  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.162  -0.604  -0.743  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.864  -0.177  -0.553  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.625   0.772   0.400  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.713   1.237   1.110  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.541   2.126   2.014  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.921   0.791   0.883  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.725   1.326   0.700  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.798   0.745  -0.159  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.776   1.493  -1.354  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.177   0.898   0.402  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.384   0.177   1.710  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.496   2.318   0.657  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.670   3.245   0.742  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.903   2.660   0.823  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.894   1.915   0.371  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.596   0.657  -0.347  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.306  -0.449   0.379  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.345   0.799  -1.689  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.176   0.417  -0.661  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.877   1.230  -1.788  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.885  -0.985  -1.084  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.478  -1.026  -1.689  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.514  -0.669  -0.604  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.382  -1.684   0.464  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.224  -0.639  -1.259  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.622  -0.017   0.574  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.941  -0.386   0.450  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.937   0.194   1.263  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.527   1.172   2.212  0.00  0.00           C+0
HETATM   37  H   UNK     0       8.744  -2.320  -2.604  0.00  0.00           H+0
HETATM   38  H   UNK     0       8.357  -3.607  -1.443  0.00  0.00           H+0
HETATM   39  H   UNK     0      10.031  -2.928  -1.543  0.00  0.00           H+0
HETATM   40  H   UNK     0       6.588  -2.643  -2.005  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.233  -1.963  -1.761  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.339  -1.352  -1.497  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.937   1.284   1.774  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.564   2.422   0.453  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.539   2.410  -1.110  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.046  -0.704   1.579  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.953   0.816   2.453  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.439  -0.057   2.238  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.196   3.576   1.344  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.939   2.168   0.494  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.391  -0.246   1.472  0.00  0.00           H+0
HETATM   52  H   UNK     0      -7.386  -0.521   0.044  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.892  -1.439   0.246  0.00  0.00           H+0
HETATM   54  H   UNK     0      -6.002   1.746  -2.158  0.00  0.00           H+0
HETATM   55  H   UNK     0      -6.206  -0.085  -2.320  0.00  0.00           H+0
HETATM   56  H   UNK     0      -7.410   0.918  -1.425  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.234   0.828  -2.618  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.900  -1.732  -0.299  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.571  -1.262  -1.884  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.443  -0.186  -2.442  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.273  -1.969  -2.200  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.808  -2.551   0.010  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.276  -2.128   0.868  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.659  -1.289   1.223  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.354   0.736   1.315  0.00  0.00           H+0
HETATM   66  H   UNK     0       8.373   1.479   2.855  0.00  0.00           H+0
HETATM   67  H   UNK     0       7.141   2.074   1.696  0.00  0.00           H+0
HETATM   68  H   UNK     0       6.691   0.786   2.854  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   40                                                  
CONECT    5    4    6   41                                                  
CONECT    6    5    7   33                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   42                                                  
CONECT    9    8   10   32                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7                                                       
CONECT   14   10   15   43   44                                             
CONECT   15   14   16   17   30                                             
CONECT   16   15   45                                                       
CONECT   17   15   18   19   26                                             
CONECT   18   17   46   47   48                                             
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   49                                                  
CONECT   22   21   23   50                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23   51   52   53                                             
CONECT   25   23   54   55   56                                             
CONECT   26   23   27   28   17                                             
CONECT   27   26   57                                                       
CONECT   28   26   29   58   59                                             
CONECT   29   28   30   60   61                                             
CONECT   30   29   31   32   15                                             
CONECT   31   30   62   63   64                                             
CONECT   32   30    9                                                       
CONECT   33    6   34   65                                                  
CONECT   34   33   35    3                                                  
CONECT   35   34   36                                                       
CONECT   36   35   66   67   68                                             
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    8                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   16                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   31                                                            
CONECT   63   31                                                            
CONECT   64   31                                                            
CONECT   65   33                                                            
CONECT   66   36                                                            
CONECT   67   36                                                            
CONECT   68   36                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  144    0
END

RDKit          3D

68 72  0  0  0  0  0  0  0  0999 V2000
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  1  2  1  0
  2  3  1  0
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  6 33  1  0
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 13  7  1  0
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  1 37  1  0
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 36 68  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₈

Average Mass

496.5560 Da

Monoisotopic Mass

496.20972 Da

IUPAC Name

(5aR,7aR,11aS,11bS)-3-(3,4-dimethoxyphenyl)-7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-1,5a,6,7,7a,8,11,11a,11b,12-decahydro-2,5-dioxatetraphene-1,11-dione

Traditional Name

(5aR,7aR,11aS,11bS)-3-(3,4-dimethoxyphenyl)-7a,11b-dihydroxy-5a,8,8,11a-tetramethyl-7,12-dihydro-6H-2,5-dioxatetraphene-1,11-dione

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C(C=C1)C1=CC2=C(C[C@@]3(O)[C@@](C)(CC[C@@]4(O)C(C)(C)C=CC(=O)[C@]34C)O2)C(=O)O1

InChI Identifier

InChI=1S/C28H32O8/c1-24(2)10-9-22(29)26(4)27(24,31)12-11-25(3)28(26,32)15-17-20(36-25)14-19(35-23(17)30)16-7-8-18(33-5)21(13-16)34-6/h7-10,13-14,31-32H,11-12,15H2,1-6H3/t25-,26+,27-,28-/m1/s1

InChI Key

MIHBCQWIBJDVPX-JUDWXZBOSA-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
Penicillium	NPAtlas	8823505

Species Where Detected

Species Name	Source	Reference
Penicillium sp. FO-4259	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	2.85	ALOGPS
logP	2.66	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	133.88 m³·mol⁻¹	ChemAxon
Polarizability	52.91 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA003111

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016246

Chemspider ID

8430760

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Arisugacin A

METLIN ID

Not Available

PubChem Compound

10255275

PDB ID

Not Available

ChEBI ID

65435

Good Scents ID

Not Available

References

General References

Al-Rashid ZF, Hsung RP: A computational view on the significance of E-ring in binding of (+)-arisugacin A to acetylcholinesterase. Bioorg Med Chem Lett. 2015 Nov 1;25(21):4848-4853. doi: 10.1016/j.bmcl.2015.06.047. Epub 2015 Jun 27. [PubMed:26159481 ]
Al-Rashid ZF, Hsung RP: (+)-Arisugacin A--computational evidence of a dual binding site covalent inhibitor of acetylcholinesterase. Bioorg Med Chem Lett. 2011 May 1;21(9):2687-91. doi: 10.1016/j.bmcl.2010.12.041. Epub 2010 Dec 16. [PubMed:21216144 ]
Sunazuka T, Handa M, Nagai K, Shirahata T, Harigaya Y, Otoguro K, Kuwajima I, Omura S: The first total synthesis of (+/-)-arisugacin A, a potent, orally bioavailable inhibitor of acetylcholinesterase. Org Lett. 2002 Feb 7;4(3):367-9. doi: 10.1021/ol017046x. [PubMed:11820881 ]

Showing NP-Card for Arisugacin A (NP0023255)

MOL for NP0023255 (Arisugacin A)

3D MOL for NP0023255 (Arisugacin A)

3D SDF for NP0023255 (Arisugacin A)

3D-SDF for NP0023255 (Arisugacin A)

PDB for NP0023255 (Arisugacin A)

3D PDB for NP0023255 (Arisugacin A)

SMILES for NP0023255 (Arisugacin A)

INCHI for NP0023255 (Arisugacin A)

Structure for NP0023255 (Arisugacin A)

3D Structure for NP0023255 (Arisugacin A)