InChI=1/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+/t12-/m0/s1

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Inherent Properties, Identifiers and References

ChemSpider ID:	4444897
Empirical Formula:	C₁₈H₂₂O₅
Molecular Weight:	318.3643
Nominal Mass:	318 Da
Average Mass:	318.3643 Da
Monoisotopic Mass:	318.146724 Da

Systematic Name:

(4S,12E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione

SMILES:

O=C1O[C@H](CCCC(=O)CCC\C=C\c2cc(O)cc(O)c12)C

InChI:

InChI=1/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+/t12-/m0/s1

InChIKey:

MBMQEIFVQACCCH-QBODLPLBBS

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Wikipedia Article(s)

Zearalenone (ZEA), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Fusarium species. Several Fusarium species produce toxic substances of considerable concern to livestock and poultry producers: namely, deoxynivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS) and zearalenone Zearalenone is the primary toxin causing infertility, abortion or other breeding problems, especially in swine. Zearalenone is heat-stable and is found worldwide in a number of cereal crops, such as maize, barley, oats, wheat, rice, and sorghum (Kuiper-Goodman et al., 1987; Tanaka et al., 1988a) and also in bread. Read more... or Edit at Wikipedia...

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Supplemental Information

Links & References

Nicolas Winssinger and Sofia Barluenga. Chemistry and biology of resorcylic acid lactones, Chem. Commun., 2007, 22-36

[DOI: 10.1039/b610344h]

Recent developments regarding the chemistry and biology of resorcylic acid lactones are reviewed.

Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

17924-92-4 [RN]

241-864-0 [EINECS/ELINCS]

6-(10-Hydroxy-6-oxo-trans-1-undecenyl)-b-resorcylic Acid Lactone

Zearalenone [Wiki]

(-)-Zearalenone

(3S,11E)-14,16-dihydroxy-3-methyl-3,4,5,6,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione

(S)-(-)-Zearalenone

(S)-Zearalenone

[S-(E)]-3,4,5,6,9,10-hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione

1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,5,6,9,10-hexahydro-14,16-dihydroxy-3-methyl-, (3S,11E)-

More...

Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

Predicted Properties

LogP:	ACD/LogP: 3.83	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	3.82	ACD/LogD (pH 7.4):	3.52
ACD/BCF (pH 5.5):	471.05	ACD/BCF (pH 7.4):	236.86
ACD/KOC (pH 5.5):	2840.94	ACD/KOC (pH 7.4):	1428.5
#H bond acceptors:	5	#H bond donors:	2
#Freely Rotating Bonds:	2	Polar Surface Area:	61.83 Å²
Index of Refraction:	1.538	Molar Refractivity:	85.26 cm³
Molar Volume:	272.3 cm³	Polarizability:	33.8 10^-24cm³
Surface Tension:	43.6 dyne/cm	Density:	1.168 g/cm³
Flash Point:	219.5 °C	Enthalpy of Vaporization:	92.66 kJ/mol
Boiling Point:	600.4 °C at 760 mmHg	Vapour Pressure:	5.21E-15 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.58

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  510.12  (Adapted Stein & Brown method)
    Melting Pt (deg C):  217.32  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.07E-011  (Modified Grain method)
    MP  (exp database):  164.5 deg C
    Subcooled liquid VP: 2.93E-010 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  31.76
       log Kow used: 3.58 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  209.3 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Phenols
       Salicylates

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.65E-013  atm-m3/mole
   Group Method:   2.28E-017  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.411E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.58  (KowWin est)
  Log Kaw used:  -10.721  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.301
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0086
   Biowin2 (Non-Linear Model)     :   0.9808
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7261  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6745  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5149
   Biowin6 (MITI Non-Linear Model):   0.3095
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3206
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  3.91E-008 Pa (2.93E-010 mm Hg)
  Log Koa (Koawin est  ): 14.301
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  76.8 
       Octanol/air (Koa) model:  49.1 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  73.9111 E-12 cm3/molecule-sec
      Half-Life =     0.145 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.737 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    13.650000 E-17 cm3/molecule-sec
      Half-Life =     0.084 Days (at 7E11 mol/cm3)
      Half-Life =      2.015 Hrs
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  7931
      Log Koc:  3.899 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.058 (BCF = 114.4)
       log Kow used: 3.58 (estimated)

 Volatilization from Water:
    Henry LC:  4.65E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.247E+009  hours   (9.361E+007 days)
    Half-Life from Model Lake : 2.451E+010  hours   (1.021E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              14.98  percent
    Total biodegradation:        0.20  percent
    Total sludge adsorption:    14.78  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00339         1.28         1000       
   Water     11.9            900          1000       
   Soil      87.1            1.8e+003     1000       
   Sediment  1.04            8.1e+003     0          
     Persistence Time: 1.77e+003 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 4, 1, 0, 2, 4, 15, 2, 1, 2, 6, 2, 2, 1, 2, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.03
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Kinases	HSP90, human heat shock protein 90	1uy6	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Serine Proteases	Thrombin	1ba8	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Serine Proteases	Trypsin	1bju	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00