NP-MRD: Showing NP-Card for aurofusarin (NP0311280)

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Record Information

Version

2.0

Created at

2022-09-11 07:10:23 UTC

Updated at

2022-09-11 07:10:24 UTC

NP-MRD ID

NP0311280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aurofusarin

Description

Aurofusarin, also known as airofusorin, belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. aurofusarin is found in Fusarium graminearum. Aurofusarin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514542D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161514542D          

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 28 29  2  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  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 30 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 28 39  1  0  0  0  0
 39 40  1  0  0  0  0
 22 40  1  0  0  0  0
 40 41  2  0  0  0  0
 32 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311280

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C(=O)C2=C(O)C3=C(OC(C)=CC3=O)C=C2C1=O)C1=C(OC)C(=O)C2=CC3=C(C(=O)C=C(C)O3)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H18O12/c1-9-5-13(31)19-15(41-9)7-11-17(25(19)35)27(37)21(29(39-3)23(11)33)22-28(38)18-12(24(34)30(22)40-4)8-16-20(26(18)36)14(32)6-10(2)42-16/h5-8,35-36H,1-4H3

> <INCHI_KEY>
VSWWTKVILIZDGX-UHFFFAOYSA-N

> <FORMULA>
C30H18O12

> <MOLECULAR_WEIGHT>
570.462

> <EXACT_MASS>
570.07982602

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
56.08791853697289

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-7-{5-hydroxy-8-methoxy-2-methyl-4,6,9-trioxo-4H,6H,9H-cyclohexa[g]chromen-7-yl}-8-methoxy-2-methyl-4H,6H,9H-cyclohexa[g]chromene-4,6,9-trione

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
3.4046973266666667

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.044025310233164

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.441935705850594

> <JCHEM_PKA_STRONGEST_BASIC>
-4.519158623055381

> <JCHEM_POLAR_SURFACE_AREA>
179.8

> <JCHEM_REFRACTIVITY>
149.57379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7-{5-hydroxy-8-methoxy-2-methyl-4,6,9-trioxocyclohexa[g]chromen-7-yl}-8-methoxy-2-methylcyclohexa[g]chromene-4,6,9-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    7   20                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
CONECT   22    4   23   40                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   39                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   42                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   30   37                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   28   40                                                  
CONECT   40   39   22   41                                                  
CONECT   41   40                                                            
CONECT   42   32                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
5,5'-Dihydroxy-8,8'-dimethoxy-2,2'-dimethyl-4H,4'H-7,7'-bibenzo(g)chromene-4,4',6,6',9,9'-hexone	MeSH
Airofusorin	MeSH

Chemical Formula

C₃₀H₁₈O₁₂

Average Mass

570.4620 Da

Monoisotopic Mass

570.07983 Da

IUPAC Name

5-hydroxy-7-{5-hydroxy-8-methoxy-2-methyl-4,6,9-trioxo-4H,6H,9H-cyclohexa[g]chromen-7-yl}-8-methoxy-2-methyl-4H,6H,9H-cyclohexa[g]chromene-4,6,9-trione

Traditional Name

5-hydroxy-7-{5-hydroxy-8-methoxy-2-methyl-4,6,9-trioxocyclohexa[g]chromen-7-yl}-8-methoxy-2-methylcyclohexa[g]chromene-4,6,9-trione

CAS Registry Number

Not Available

SMILES

COC1=C(C(=O)C2=C(O)C3=C(OC(C)=CC3=O)C=C2C1=O)C1=C(OC)C(=O)C2=CC3=C(C(=O)C=C(C)O3)C(O)=C2C1=O

InChI Identifier

InChI=1S/C30H18O12/c1-9-5-13(31)19-15(41-9)7-11-17(25(19)35)27(37)21(29(39-3)23(11)33)22-28(38)18-12(24(34)30(22)40-4)8-16-20(26(18)36)14(32)6-10(2)42-16/h5-8,35-36H,1-4H3

InChI Key

VSWWTKVILIZDGX-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

Species Name	Source	Reference
Fusarium graminearum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Chromone
Benzopyran
Naphthalene
1-benzopyran
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Vinylogous ester
Vinylogous acid
Heteroaromatic compound
Ketone
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
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	3.85	ALOGPS
logP	3.4	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	5.44	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	179.8 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	149.57 m³·mol⁻¹	ChemAxon
Polarizability	56.09 Å³	ChemAxon
Number of Rings	6	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

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

99586

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for aurofusarin (NP0311280)

MOL for NP0311280 (aurofusarin)

3D MOL for NP0311280 (aurofusarin)

3D SDF for NP0311280 (aurofusarin)

3D-SDF for NP0311280 (aurofusarin)

PDB for NP0311280 (aurofusarin)

3D PDB for NP0311280 (aurofusarin)

SMILES for NP0311280 (aurofusarin)

INCHI for NP0311280 (aurofusarin)

Structure for NP0311280 (aurofusarin)

3D Structure for NP0311280 (aurofusarin)