NP-MRD: Showing NP-Card for Rubratoxin A (NP0138951)

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Record Information

Version

1.0

Created at

2022-06-29 19:33:05 UTC

Updated at

2022-06-29 19:33:05 UTC

NP-MRD ID

NP0138951

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rubratoxin A

Description

Rubratoxin A belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Rubratoxin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Rubratoxin A is a potentially toxic compound. Rubratoxin A is a potent inhibitor of protein phosphatase 2A, exerting antitumor and antimetastatic effects. Rubratoxin A has also been shown to inhibit Na+/K+-transporting ATPases. Studies on Rubratoxin A however have also indicated it may also have valuable antitumor and antimetastatic effects. Rubratoxin A is a mycotoxin produced by fungi such as Penicillum rubrum and Penicillum purpurogenum, which are common soil fungi that sometimes contaminate animal feeds. Rubratoxins are hepatotoxic, nephrotoxic, and splenotoxic, causing congestive, hemorrhagic and degenerative lesions. Inhibition may cause the phosphorylation of CREB and subsequent activation of natural killer cells via the stimulation of interleukin-2 release from T cells, contributing to antimetastatic effects. Focal adhesion kinase phosphorylation and paxillin phosphorylation that interfere with cell adhesion could be another antimetastatic effect. Rubratoxins have been shown to be hepatotoxic, nephrotoxic, and splenotoxic.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212392D          

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M  END

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  Mrv0541 02241212392D          

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 22 23  1  0  0  0  0
 23 24  1  0  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  2  0  0  0  0
 27 29  1  0  0  0  0
 23 29  1  0  0  0  0
 22 30  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  2  0  0  0  0
  9 36  1  0  0  0  0
  7 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138951

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(O)C1C(O)C2=C(CC(CC3=C1C(=O)OC3O)C(O)C1CC=CC(=O)O1)C(=O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O11/c1-2-3-4-5-7-15(27)20-18-13(23(31)36-25(18)33)10-12(21(29)16-8-6-9-17(28)35-16)11-14-19(22(20)30)26(34)37-24(14)32/h6,9,12,15-16,20-23,27,29-31H,2-5,7-8,10-11H2,1H3

> <INCHI_KEY>
XOEFANNJIKAWGX-UHFFFAOYSA-N

> <FORMULA>
C26H32O11

> <MOLECULAR_WEIGHT>
520.5257

> <EXACT_MASS>
520.194461866

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
52.800797820607855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,13-dihydroxy-10-[hydroxy(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl]-2-(1-hydroxyheptyl)-6,14-dioxatricyclo[10.3.0.0⁴,⁸]pentadeca-1(12),4(8)-diene-5,7,15-trione

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.8374377413333325

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.982571728341536

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.818870700637414

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8988760446550055

> <JCHEM_POLAR_SURFACE_AREA>
176.89

> <JCHEM_REFRACTIVITY>
126.96669999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rubratoxin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.067  -5.181   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.734  -4.411   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.400  -5.181   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.066  -4.411   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.733  -5.181   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.399  -4.411   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.935  -5.181   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.268  -4.411   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.001  -2.894   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.771  -1.561   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.218  -1.034   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.665  -1.561   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.435  -2.894   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.168  -4.411   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.988  -5.401   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.448  -5.401   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.972  -6.865   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.508  -7.341   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.218  -7.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.464  -6.865   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.929  -7.341   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.952  -2.627   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.942  -3.807   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.458  -3.539   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.448  -4.719   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.921  -6.166   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.405  -6.433   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.878  -7.880   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.415  -5.254   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.478  -1.180   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.164   0.505   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.378   1.453   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.684   0.930   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.823  -0.347   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.284  -0.401   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.484  -2.627   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.935  -6.721   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   36                                                  
CONECT   10    9   11   34                                                  
CONECT   11   10   12   31                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15    8   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   13   23   30                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   23                                                       
CONECT   30   22                                                            
CONECT   31   11   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   10   35                                                  
CONECT   35   34                                                            
CONECT   36    9                                                            
CONECT   37    7                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₁

Average Mass

520.5257 Da

Monoisotopic Mass

520.19446 Da

IUPAC Name

3,13-dihydroxy-10-[hydroxy(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl]-2-(1-hydroxyheptyl)-6,14-dioxatricyclo[10.3.0.0⁴,⁸]pentadeca-1(12),4(8)-diene-5,7,15-trione

Traditional Name

rubratoxin A

CAS Registry Number

Not Available

SMILES

CCCCCCC(O)C1C(O)C2=C(CC(CC3=C1C(=O)OC3O)C(O)C1CC=CC(=O)O1)C(=O)OC2=O

InChI Identifier

InChI=1S/C26H32O11/c1-2-3-4-5-7-15(27)20-18-13(23(31)36-25(18)33)10-12(21(29)16-8-6-9-17(28)35-16)11-14-19(22(20)30)26(34)37-24(14)32/h6,9,12,15-16,20-23,27,29-31H,2-5,7-8,10-11H2,1H3

InChI Key

XOEFANNJIKAWGX-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Fatty alcohol
Dihydropyranone
2-furanone
Fatty acyl
Pyran
Carboxylic acid anhydride
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.03	ALOGPS
logP	1.84	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	5.82	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	176.89 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	126.97 m³·mol⁻¹	ChemAxon
Polarizability	52.8 Å³	ChemAxon
Number of Rings	4	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

Not Available

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

31181

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rubratoxin A (NP0138951)

MOL for NP0138951 (Rubratoxin A)

3D MOL for NP0138951 (Rubratoxin A)

3D SDF for NP0138951 (Rubratoxin A)

3D-SDF for NP0138951 (Rubratoxin A)

PDB for NP0138951 (Rubratoxin A)

3D PDB for NP0138951 (Rubratoxin A)

SMILES for NP0138951 (Rubratoxin A)

INCHI for NP0138951 (Rubratoxin A)

Structure for NP0138951 (Rubratoxin A)

3D Structure for NP0138951 (Rubratoxin A)