NP-MRD: Showing NP-Card for Aflatoxin B1 (NP0048414)

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Record Information

Version

2.0

Created at

2022-03-17 20:56:06 UTC

Updated at

2024-09-03 04:15:01 UTC

NP-MRD ID

NP0048414

Natural Product DOI

https://doi.org/10.57994/0124

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aflatoxin B1

Description

Aflatoxin B1 is found in Aspergillus flavus, Aspergillus nomius, Aspergillus parasiticus, Homo sapiens and Streptomyces roseolus.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231220432D          

 23 27  0  0  0  0            999 V2000
   16.0372   -6.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7808   -5.6189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5191   -4.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9611   -6.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0815   -3.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2567   -2.9276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0372   -5.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8178   -5.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5558   -5.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5323   -5.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2467   -5.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8178   -6.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9974   -5.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8085   -5.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5558   -4.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0041   -4.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2467   -6.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3154   -4.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5323   -6.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8191   -3.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7808   -4.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2598   -3.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9611   -7.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 12  1  0  0  0  0
  2  9  1  0  0  0  0
  2 21  1  0  0  0  0
  3 10  1  0  0  0  0
  3 22  1  0  0  0  0
  4 17  1  0  0  0  0
  4 23  1  0  0  0  0
  5 20  2  0  0  0  0
  6 22  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 15  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 11 17  2  0  0  0  0
 12 19  2  0  0  0  0
 13 14  1  0  0  0  0
 13 16  2  0  0  0  0
 14 18  1  0  0  0  0
 15 21  2  0  0  0  0
 16 20  1  0  0  0  0
 16 22  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048414

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C2C3C=COC3OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3

> <INCHI_KEY>
OQIQSTLJSLGHID-UHFFFAOYSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.2736

> <EXACT_MASS>
312.063388116

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.07014881116413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.5843809030000005

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.787312891010785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4404302662976205

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
78.58509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aflatoxin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      29.936 -12.201   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      27.591 -10.489   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      32.702  -7.818   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      35.394 -12.501   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      37.485  -5.870   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      34.079  -5.465   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      29.936  -9.722   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.393 -10.191   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.037 -10.961   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.727  -9.421   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.061 -10.191   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.393 -11.731   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.462  -9.411   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.976  -9.911   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.037  -8.494   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.474  -7.807   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      34.061 -11.731   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.922  -8.628   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.727 -12.501   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.996  -7.330   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.591  -8.967   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      34.085  -7.005   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      35.394 -14.041   0.000  0.00  0.00           C+0
CONECT    1    9   12                                                       
CONECT    2    9   21                                                       
CONECT    3   10   22                                                       
CONECT    4   17   23                                                       
CONECT    5   20                                                            
CONECT    6   22                                                            
CONECT    7    8    9   15                                                  
CONECT    8    7   10   12                                                  
CONECT    9    1    2    7                                                  
CONECT   10    3    8   11                                                  
CONECT   11   10   13   17                                                  
CONECT   12    1    8   19                                                  
CONECT   13   11   14   16                                                  
CONECT   14   13   18                                                       
CONECT   15    7   21                                                       
CONECT   16   13   20   22                                                  
CONECT   17    4   11   19                                                  
CONECT   18   14   20                                                       
CONECT   19   12   17                                                       
CONECT   20    5   16   18                                                  
CONECT   21    2   15                                                       
CONECT   22    3    6   16                                                  
CONECT   23    4                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Value	Source
AFB1	HMDB
AFBI	HMDB
HSDB-3453	MeSH, HMDB
Aflatoxin b	MeSH, HMDB
Aflatoxin b1, (6ar-cis)-isomer, 14C-labeled	MeSH, HMDB
Aflatoxin b1, (6ar-cis)-isomer, 2H-labeled	MeSH, HMDB
HSDB 3453	MeSH, HMDB
Aflatoxin b1 dihydrochloride, (6ar-cis)-isomer	MeSH, HMDB
Aflatoxin b1, cis(+,-)-isomer	MeSH, HMDB
Aflatoxin b1, (6ar-cis)-isomer, 3H-labeled	MeSH, HMDB

Chemical Formula

C₁₇H₁₂O₆

Average Mass

312.2736 Da

Monoisotopic Mass

312.06339 Da

IUPAC Name

11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione

Traditional Name

aflatoxin

CAS Registry Number

1162-65-8

SMILES

COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C2C3C=COC3OC2=C1

InChI Identifier

InChI=1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3

InChI Key

OQIQSTLJSLGHID-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Merangelgri			2022-10-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2023-01-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2023-01-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2022-12-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2022-12-21	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Aspergillus flavus	Fungi	KNApSAcK
Aspergillus nomius	Fungi	KNApSAcK
Aspergillus parasiticus	Fungi	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Streptomyces roseolus	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as difurocoumarocyclopentenones. These are polycyclic aromatic compounds containing a cyclopenten-2-one 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

Difurocoumarocyclopentenones

Alternative Parents

Substituents

Difurocoumarocyclopentenone
Benzopyran
1-benzopyran
Coumaran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Dihydrofuran
Lactone
Ketone
Ether
Acetal
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Aflatoxins and related substances (C06800 )
Aflatoxins (C06800 )
Aflatoxins and related substances (LMPK10000006 )
a secondary metabolite (CPD-4592 )

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	1.73	ALOGPS
logP	1.58	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.59 m³·mol⁻¹	ChemAxon
Polarizability	30.07 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014816

KNApSAcK ID

C00000546

Chemspider ID

Not Available

KEGG Compound ID

C06800

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aflatoxin B1

METLIN ID

Not Available

PubChem Compound

14403

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Aflatoxin B1 (NP0048414)

MOL for NP0048414 (Aflatoxin B1)

3D MOL for NP0048414 (Aflatoxin B1)

3D SDF for NP0048414 (Aflatoxin B1)

3D-SDF for NP0048414 (Aflatoxin B1)

PDB for NP0048414 (Aflatoxin B1)

3D PDB for NP0048414 (Aflatoxin B1)

SMILES for NP0048414 (Aflatoxin B1)

INCHI for NP0048414 (Aflatoxin B1)

Structure for NP0048414 (Aflatoxin B1)

3D Structure for NP0048414 (Aflatoxin B1)