NP-MRD: Showing NP-Card for aflatoxin (NP0213450)

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Record Information

Version

2.0

Created at

2022-09-05 12:26:26 UTC

Updated at

2022-09-05 12:26:26 UTC

NP-MRD ID

NP0213450

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aflatoxin

Description

Aflatoxin G belongs to the class of organic compounds known as difurocoumarolactones. These are polycyclic aromatic compounds containing a delta-valerolactone ring fused to the coumarin moiety of the difurocoumarin skeleton. Aflatoxin G is an extremely weak basic (essentially neutral) compound (based on its pKa). Aflatoxin G is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. In addition to randomly mutating DNA, this is thought to cause mutations in the p53 gene, an important gene in preventing cell cycle progression when there are DNA mutations, or signaling apoptosis. Aflatoxins are metabolized in the liver by the cytochrome P-450-dependent polysubstrate mono-oxygenase system to less toxic metabolites. Protracted exposure to aflatoxins may cause liver damage and necrosis, cholestasis, and hepatomas. Aflatoxins modify the immune system by affecting antibody formation, complement, cell-mediated immunity, and phagocytosis. aflatoxin is found in Zea mays. Aflatoxin G belongs to the family of Difurocoumarolactone Series.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 40  0  0  0  0  0  0  0  0999 V2000
   -1.6237    3.4494    0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7096    2.0441   -0.0768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421    1.3118   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6944    1.9720   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8858    1.2648   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421   -0.1066   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6011   -0.7463   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051   -2.0504   -0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947   -2.7478   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5054   -3.9987   -0.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185   -2.0987   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8018   -0.7144   -0.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5960   -0.0525   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081   -0.0049   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2157   -1.0012    0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1333   -2.2053   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9353   -2.8894   -0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8788   -4.1558   -0.6526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2464   -0.5573   -0.2825 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7546   -0.8911    1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883   -0.2323    1.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2143    0.5496    0.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386    0.6973   -0.5913 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1923    1.7150   -0.0966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6557    3.8343    0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684    3.7024    0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    3.8400   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783    3.0287    0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028    0.6409    0.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4183    0.5273   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2902   -1.1966    1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2016   -0.5296   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4508   -1.3360   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857   -1.5545    1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4476   -0.3086    2.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2543    0.8006   -1.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  6  7  1  0
  7 13  2  0
 13 12  1  0
 12 11  2  0
 11 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
 13  3  1  0
 14 12  1  0
 24  5  1  0
  8  7  1  0
 23 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 19 33  1  6
 20 34  1  0
 21 35  1  0
 23 36  1  6
 15 31  1  0
 15 32  1  0
 14 29  1  0
 14 30  1  0
M  END


  Mrv0541 09061400402D          

 24 28  0  0  0  0            999 V2000
    7.7967    1.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9040    0.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317   -0.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6661    0.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1206   -0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6178    1.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2493    0.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3256   -0.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    1.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9631    1.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4872    0.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0704    0.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3566   -0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8325   -0.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1187   -0.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7019   -1.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7580    0.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2260   -1.7935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8092   -1.9794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0346    1.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7734   -0.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0132    0.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1520    1.2573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9398   -0.8454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  2  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 13  1  0  0  0  0
 17  8  1  0  0  0  0
 18 15  2  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20  9  1  0  0  0  0
 21  4  1  0  0  0  0
 21 15  1  0  0  0  0
 22  5  1  0  0  0  0
 22 17  1  0  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213450

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)OCC1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O7/c1-20-9-6-10-12(8-3-5-22-17(8)23-10)14-11(9)7-2-4-21-15(18)13(7)16(19)24-14/h3,5-6,8,17H,2,4H2,1H3

> <INCHI_KEY>
XWIYFDMXXLINPU-UHFFFAOYSA-N

> <FORMULA>
C17H12O7

> <MOLECULAR_WEIGHT>
328.273

> <EXACT_MASS>
328.058302738

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.89116476026056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-methoxy-6,8,16,20-tetraoxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹³,¹⁸]icosa-1(12),2(9),4,10,13(18)-pentaene-17,19-dione

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.3682086073333335

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.440284853007925

> <JCHEM_POLAR_SURFACE_AREA>
80.29000000000002

> <JCHEM_REFRACTIVITY>
79.8478

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aflatoxin G1

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-14         0                                  
HETATM    1  C   UNK     0      14.554   2.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.754   1.233   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.339  -1.477   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.177   0.643   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.825  -1.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.487   3.003   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.532   0.296   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.075  -0.124   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.909   2.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.264   2.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.109   0.886   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.465   0.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.732  -1.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.887  -0.051   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.155  -1.821   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.510  -2.168   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.015   0.994   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.355  -3.348   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.711  -3.695   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.131   3.350   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      16.377  -0.884   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.625   0.331   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.750   2.347   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      11.088  -1.578   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    4    7                                                       
CONECT    3    5    8                                                       
CONECT    4    2   21                                                       
CONECT    5    3   22                                                       
CONECT    6    9   10                                                       
CONECT    7    2   11   13                                                  
CONECT    8    3   12   17                                                  
CONECT    9    6   11   20                                                  
CONECT   10    6   12   23                                                  
CONECT   11    7    9   14                                                  
CONECT   12    8   10   14                                                  
CONECT   13    7   15   16                                                  
CONECT   14   11   12   24                                                  
CONECT   15   13   18   21                                                  
CONECT   16   13   19   24                                                  
CONECT   17    8   22   23                                                  
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20    1    9                                                       
CONECT   21    4   15                                                       
CONECT   22    5   17                                                       
CONECT   23   10   17                                                       
CONECT   24   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Value	Source
Aflatoxin g1	HMDB

Chemical Formula

C₁₇H₁₂O₇

Average Mass

328.2730 Da

Monoisotopic Mass

328.05830 Da

IUPAC Name

11-methoxy-6,8,16,20-tetraoxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹³,¹⁸]icosa-1(12),2(9),4,10,13(18)-pentaene-17,19-dione

Traditional Name

aflatoxin G1

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)OCC1)C(=O)O2

InChI Identifier

InChI=1S/C17H12O7/c1-20-9-6-10-12(8-3-5-22-17(8)23-10)14-11(9)7-2-4-21-15(18)13(7)16(19)24-14/h3,5-6,8,17H,2,4H2,1H3

InChI Key

XWIYFDMXXLINPU-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
Zea mays	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as difurocoumarolactones. These are polycyclic aromatic compounds containing a delta-valerolactone ring fused to the coumarin moiety of the difurocoumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Difurocoumarolactones

Alternative Parents

Substituents

Difurocoumarolactone
Benzopyran
1-benzopyran
Coumaran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Dihydrofuran
Carboxylic acid ester
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a secondary metabolite (CPD-10178 )

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	1.81	ALOGPS
logP	1.37	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	80.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.85 m³·mol⁻¹	ChemAxon
Polarizability	30.89 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030474

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14421

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for aflatoxin (NP0213450)

MOL for NP0213450 (aflatoxin)

3D MOL for NP0213450 (aflatoxin)

3D SDF for NP0213450 (aflatoxin)

3D-SDF for NP0213450 (aflatoxin)

PDB for NP0213450 (aflatoxin)

3D PDB for NP0213450 (aflatoxin)

SMILES for NP0213450 (aflatoxin)

INCHI for NP0213450 (aflatoxin)

Structure for NP0213450 (aflatoxin)

3D Structure for NP0213450 (aflatoxin)