NP-MRD: Showing NP-Card for (S,E)-Zearalenone (NP0047322)

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Record Information

Version

2.0

Created at

2022-03-17 20:38:15 UTC

Updated at

2022-03-17 20:38:15 UTC

NP-MRD ID

NP0047322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S,E)-Zearalenone

Description

(S,E)-Zearalenone, also known as zearalenone, belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene (S,E)-Zearalenone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (S,E)-Zearalenone has been detected, but not quantified in, corns. This could make (S,e)-zearalenone a potential biomarker for the consumption of these foods. Zearalenone is a reproductive toxin and has been shown to cause infertility, abortion or other breeding problems in livestock. Zearalenone is also immunotoxic, genotoxic, and can cause kidney and liver damage. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. In humans, Zearalenone has been shown to cause an earlier onset of puberty in children, endometrial adenocarcinomas, hyperplasia and breast cancer in women. Zearalenone's genotoxicity results from it's ability to cause DNA fragmentation, chromosome aberrations, and DNA adduct formation (S,E)-Zearalenone is a potentially toxic compound. It exerts cytotoxic effects by enhancing lipid peroxidation, increasing oxidative stress, and inducing apoptosis. (S,E)-Zearalenone is found in Gibberella zeae. Zearalenone is rapidly absorbed after oral administration.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 09061400432D          

 25 26  0  0  0  0            999 V2000
    5.9503   -4.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1484   -0.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3558   -0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7429   -1.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1392   -2.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9411   -3.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576   -1.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5355   -0.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9318   -2.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705   -1.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797   -2.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1484   -3.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3650   -1.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1300   -1.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9779   -1.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3742   -2.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668   -2.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7613   -3.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9226   -1.2617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3834   -0.9184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1760   -3.6642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5631   -4.0074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -2.9778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7613   -0.2320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521   -2.1769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 12  1  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 18  2  0  0  0  0
 23 12  1  0  0  0  0
 23 18  1  0  0  0  0
 24  3  1  0  0  0  0
 25  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C1=C([H])/C2=CC(O)=CC(O)=C2C(=O)OC(C)CCCC(=O)CCC1

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+

> <INCHI_KEY>
MBMQEIFVQACCCH-XVNBXDOJSA-N

> <FORMULA>
C18H22O5

> <MOLECULAR_WEIGHT>
318.3643

> <EXACT_MASS>
318.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.606539234404856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
4.374165605666666

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.383901133857439

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.537724054652303

> <JCHEM_PKA_STRONGEST_BASIC>
-4.015715909368844

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
88.33949999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zearalenone

> <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      11.107  -8.121   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.477  -1.074   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.997  -1.501   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.587  -2.142   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.327  -4.704   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.957  -6.199   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.628  -2.996   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.066  -1.714   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.806  -4.277   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.038  -2.355   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.189  -4.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.477  -6.626   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.148  -3.423   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.176  -2.782   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.559  -2.782   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.298  -5.345   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.778  -4.918   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.888  -5.986   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.656  -2.355   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.449  -1.714   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.929  -6.840   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.518  -7.481   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.367  -5.558   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       8.888  -0.433   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      10.737  -4.064   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7   24                                                  
CONECT    4    2    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   12                                                       
CONECT    7    3   13   25                                                  
CONECT    8    4   14                                                       
CONECT    9    5   14                                                       
CONECT   10   13   15                                                       
CONECT   11   15   16                                                       
CONECT   12    1    6   23                                                  
CONECT   13    7   10   17                                                  
CONECT   14    8    9   19                                                  
CONECT   15   10   11   20                                                  
CONECT   16   11   17   21                                                  
CONECT   17   13   16   18                                                  
CONECT   18   17   22   23                                                  
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   18                                                            
CONECT   23   12   18                                                       
CONECT   24    3                                                            
CONECT   25    7                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
Zearalenone	HMDB

Chemical Formula

C₁₈H₂₂O₅

Average Mass

318.3643 Da

Monoisotopic Mass

318.14672 Da

IUPAC Name

14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione

Traditional Name

zearalenone

CAS Registry Number

17924-92-4

SMILES

[H]\C1=C([H])/C2=CC(O)=CC(O)=C2C(=O)OC(C)CCCC(=O)CCC1

InChI Identifier

InChI=1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3+

InChI Key

MBMQEIFVQACCCH-XVNBXDOJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusarium graminearum	Fungi	KNApSAcK
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Zearalenones

Direct Parent

Zearalenones

Alternative Parents

Substituents

Zearalenone-skeleton
Dihydroxybenzoic acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Carbonyl group
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	3.04	ALOGPS
logP	4.37	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.54	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.34 m³·mol⁻¹	ChemAxon
Polarizability	33.61 Å³	ChemAxon
Number of Rings	2	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

HMDB0031752

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008421

KNApSAcK ID

Not Available

Chemspider ID

4524664

KEGG Compound ID

C09981

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5375083

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (S,E)-Zearalenone (NP0047322)

MOL for NP0047322 ((S,E)-Zearalenone)

3D MOL for NP0047322 ((S,E)-Zearalenone)

3D SDF for NP0047322 ((S,E)-Zearalenone)

3D-SDF for NP0047322 ((S,E)-Zearalenone)

PDB for NP0047322 ((S,E)-Zearalenone)

3D PDB for NP0047322 ((S,E)-Zearalenone)

SMILES for NP0047322 ((S,E)-Zearalenone)

INCHI for NP0047322 ((S,E)-Zearalenone)

Structure for NP0047322 ((S,E)-Zearalenone)

3D Structure for NP0047322 ((S,E)-Zearalenone)