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Showing NP-Card for 8,9-Epoxyaflatoxin B1 (NP0333974)

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Record Information
Version2.0
Created at2024-09-09 21:30:33 UTC
Updated at2024-09-09 21:30:33 UTC
NP-MRD IDNP0333974
Secondary Accession NumbersNone
Natural Product Identification
Common Name8,9-Epoxyaflatoxin B1
DescriptionProb. Ultimate carcinogen of Aflatoxin B1 2,3-Epoxyaflatoxin B1 is formed due to the metabolism of aflatoxin B1 (AFB1) by ; CYP2A13, an enzyme predominantly expressed in human respiratory tract, but there is no detectable AFB1 epoxide formation by CYP2A6, which was also reported to be involved in the metabolic activation of AFB1. (PMID: 16385575 ). Aflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus, most notably Aspergillus flavus and Aspergillus parasiticus. At least 13 different types of aflatoxin are produced in nature. Aflatoxin B1 is considered the most toxic and is produced by both Aspergillus flavus and Aspergillus parasiticus. The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favorable for its growth. Favorable conditions include high moisture content (at least 7%) and high temperature. Aflatoxins B1 (AFB1) are contaminants of improperly stored foods; they are potent genotoxic and carcinogenic compounds, exerting their effects through damage to DNA. They can also induce mutations that increase oxidative damage. (PMID: 17214555 ). Crops which are frequently affected by Aspergillus contamination include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333974 (8,9-Epoxyaflatoxin B1)


  Mrv2104 05252300022D          

 24 29  0  0  0  0            999 V2000
    6.7969    4.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8236    3.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2786    3.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6738    5.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285    3.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7647    2.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3694    4.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418    5.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9921    2.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    4.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9054    4.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103    3.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6010    3.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964    3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2601    2.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6553    4.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8238    3.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9848    1.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2237    1.6593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1013    5.3367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1692    5.3085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5646    2.9272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9595    2.8051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8602    4.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  6 18  2  0  0  0  0
  7 10  1  0  0  0  0
  7 20  1  0  0  0  0
  8 11  2  0  0  0  0
  8 21  1  0  0  0  0
  9 15  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 22  1  0  0  0  0
 14 17  1  0  0  0  0
 14 23  1  0  0  0  0
 15 19  2  0  0  0  0
 15 22  1  0  0  0  0
 16 21  1  0  0  0  0
 16 24  1  0  0  0  0
 17 23  1  0  0  0  0
 17 24  1  0  0  0  0
M  END
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3D MOL for NP0333974 (8,9-Epoxyaflatoxin B1)

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3D SDF for NP0333974 (8,9-Epoxyaflatoxin B1)

  Mrv2104 05252300022D          

 24 29  0  0  0  0            999 V2000
    6.7969    4.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8236    3.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2786    3.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6738    5.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285    3.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7647    2.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3694    4.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418    5.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9921    2.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    4.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9054    4.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103    3.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6010    3.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964    3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2601    2.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6553    4.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8238    3.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9848    1.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2237    1.6593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1013    5.3367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1692    5.3085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5646    2.9272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9595    2.8051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8602    4.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  6 18  2  0  0  0  0
  7 10  1  0  0  0  0
  7 20  1  0  0  0  0
  8 11  2  0  0  0  0
  8 21  1  0  0  0  0
  9 15  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 22  1  0  0  0  0
 14 17  1  0  0  0  0
 14 23  1  0  0  0  0
 15 19  2  0  0  0  0
 15 22  1  0  0  0  0
 16 21  1  0  0  0  0
 16 24  1  0  0  0  0
 17 23  1  0  0  0  0
 17 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333974

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C3C4OC4OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1/C17H12O7/c1-20-7-4-8-11(12-14-17(23-14)24-16(12)21-8)13-10(7)5-2-3-6(18)9(5)15(19)22-13/h4,12,14,16-17H,2-3H2,1H3

> <INCHI_KEY>
KHBXRZGALJGBPA-UHFFFAOYNA-N

> <FORMULA>
C17H12O7

> <MOLECULAR_WEIGHT>
328.276

> <EXACT_MASS>
328.058302726

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.020363459678983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione

> <JCHEM_LOGP>
1.5560570326666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.593072840170752

> <JCHEM_PKA_STRONGEST_BASIC>
-4.03578193218188

> <JCHEM_POLAR_SURFACE_AREA>
83.59000000000002

> <JCHEM_REFRACTIVITY>
77.0125

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333974 (8,9-Epoxyaflatoxin B1)
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PDB for NP0333974 (8,9-Epoxyaflatoxin B1)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      12.688   9.134   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.737   7.296   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.587   6.011   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.724  10.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.253   6.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.627   4.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.023   9.251   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.358   9.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.185   5.346   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.955   7.713   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.290   7.831   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.806   7.420   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.588   7.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.847   6.215   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.819   4.636   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.957   8.704   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.404   6.755   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.038   3.322   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.751   3.097   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.389   9.962   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.916   9.909   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.521   5.464   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.658   5.236   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.472   8.294   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    5                                                       
CONECT    3    2    6                                                       
CONECT    4    7    8                                                       
CONECT    5    2    9   10                                                  
CONECT    6    3    9   18                                                  
CONECT    7    4   10   20                                                  
CONECT    8    4   11   21                                                  
CONECT    9    5    6   15                                                  
CONECT   10    5    7   13                                                  
CONECT   11    8   12   13                                                  
CONECT   12   11   14   16                                                  
CONECT   13   10   11   22                                                  
CONECT   14   12   17   23                                                  
CONECT   15    9   19   22                                                  
CONECT   16   12   21   24                                                  
CONECT   17   14   23   24                                                  
CONECT   18    6                                                            
CONECT   19   15                                                            
CONECT   20    1    7                                                       
CONECT   21    8   16                                                       
CONECT   22   13   15                                                       
CONECT   23   14   17                                                       
CONECT   24   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

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3D PDB for NP0333974 (8,9-Epoxyaflatoxin B1)
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SMILES for NP0333974 (8,9-Epoxyaflatoxin B1)
COC1=CC2=C(C3C4OC4OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2
Download
INCHI for NP0333974 (8,9-Epoxyaflatoxin B1)
InChI=1/C17H12O7/c1-20-7-4-8-11(12-14-17(23-14)24-16(12)21-8)13-10(7)5-2-3-6(18)9(5)15(19)22-13/h4,12,14,16-17H,2-3H2,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC17H12O7
Average Mass328.2760 Da
Monoisotopic Mass328.05830 Da
IUPAC Name12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione
Traditional Name12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C3C4OC4OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2
InChI Identifier
InChI=1/C17H12O7/c1-20-7-4-8-11(12-14-17(23-14)24-16(12)21-8)13-10(7)5-2-3-6(18)9(5)15(19)22-13/h4,12,14,16-17H,2-3H2,1H3
InChI KeyKHBXRZGALJGBPA-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.56ChemAxon
pKa (Strongest Acidic)19.59ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area83.59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.01 m³·mol⁻¹ChemAxon
Polarizability31.02 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wood ML, Smith JR, Garner RC: Structural characterization of the major adducts obtained after reaction of an ultimate carcinogen aflatoxin B1-dichloride with calf thymus DNA in vitro. Cancer Res. 1988 Oct 1;48(19):5391-6. [PubMed:3138022  ]