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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:29:06 UTC

Update Date

2021-09-26 23:15:54 UTC

HMDB ID

HMDB0258755

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,3,7,8-Tetrachlorodibenzo-p-dioxin

Description

2,3,7,8-tetrachlorodibenzo-p-dioxin, also known as PCDD 48 or TCDD, belongs to the class of organic compounds known as chlorinated dibenzo-p-dioxins. These are organic compounds containing a chlorine atom attached to a dibenzo-p-dioxin moiety. In humans, 2,3,7,8-tetrachlorodibenzo-p-dioxin is involved in the ahr signal transduction pathway. 2,3,7,8-tetrachlorodibenzo-p-dioxin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 2,3,7,8-tetrachlorodibenzo-p-dioxin is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on 2,3,7,8-tetrachlorodibenzo-p-dioxin. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,3,7,8-tetrachlorodibenzo-p-dioxin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,3,7,8-Tetrachlorodibenzo-p-dioxin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306131822332D          

 22 24  0  0  0  0            999 V2000
   -2.7959   -0.8110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7959    0.8110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7959   -0.8110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7959    0.8110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6858    0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6858   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6858    0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6858   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3939   -0.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3939    0.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940   -0.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1116    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1116   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1115    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1115   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3882    1.3104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3882   -1.3104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3882    1.3104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3882   -1.3104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 17  1  0  0  0  0
  3 16  1  0  0  0  0
  4 15  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  2  0  0  0  0
  8 13  2  0  0  0  0
  9 10  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  2  0  0  0  0
 11 18  1  0  0  0  0
 11 22  1  0  0  0  0
 12 17  1  0  0  0  0
 12 21  1  0  0  0  0
 13 16  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258755

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C1=C2OC3=C([H])C(Cl)=C(Cl)C([H])=C3OC2=C([H])C(Cl)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H

> <INCHI_KEY>
HGUFODBRKLSHSI-UHFFFAOYSA-N

> <FORMULA>
C12H4Cl4O2

> <MOLECULAR_WEIGHT>
321.971

> <EXACT_MASS>
319.8965402

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
28.718475000650365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3,7,8-tetrachlorooxanthrene

> <ALOGPS_LOGP>
6.59

> <JCHEM_LOGP>
5.416753071333333

> <ALOGPS_LOGS>
-5.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4885740699203214

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
71.70080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.71e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dioxin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 13-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUN-18         0                                  
HETATM    1 Cl   UNK     0      -5.219  -1.514   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0      -5.219   1.514   0.000  0.00  0.00          Cl+0
HETATM    3 Cl   UNK     0       5.219  -1.514   0.000  0.00  0.00          Cl+0
HETATM    4 Cl   UNK     0       5.219   1.514   0.000  0.00  0.00          Cl+0
HETATM    5  O   UNK     0       0.000   1.478   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000  -1.478   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.280   0.739   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.280  -0.739   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.280   0.739   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.280  -0.739   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.602  -1.530   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.602   1.530   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.602  -1.530   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.602   1.530   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.942   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.942  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.941   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.941  -0.770   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       2.591   2.446   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.591  -2.446   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.591   2.446   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.591  -2.446   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   17                                                            
CONECT    3   16                                                            
CONECT    4   15                                                            
CONECT    5    7    9                                                       
CONECT    6    8   10                                                       
CONECT    7    5    8   14                                                  
CONECT    8    6    7   13                                                  
CONECT    9    5   10   12                                                  
CONECT   10    6    9   11                                                  
CONECT   11   10   18   22                                                  
CONECT   12    9   17   21                                                  
CONECT   13    8   16   20                                                  
CONECT   14    7   15   19                                                  
CONECT   15    4   14   16                                                  
CONECT   16    3   13   15                                                  
CONECT   17    2   12   18                                                  
CONECT   18    1   11   17                                                  
CONECT   19   14                                                            
CONECT   20   13                                                            
CONECT   21   12                                                            
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3,7,8-Tetrachlorodibenzodioxin	ChEBI
Dioxin	ChEBI
Dioxine	ChEBI
PCDD 48	ChEBI
TCDD	ChEBI
Tetrachlorodibenzodioxin	ChEBI
Tetradioxin	ChEBI
Dibenzodioxin, polychlorinated	MeSH
Dibenzodioxins, polychlorinated	MeSH
Polychlorinated dibenzodioxins	MeSH
Polychlorodibenzo p dioxin	MeSH
Tetrachlorodibenzo p dioxin	MeSH
Dibenzo-p-dioxins, polychlorinated	MeSH
Polychlorinated dibenzodioxin	MeSH
Polychlorodibenzo-4-dioxin	MeSH
Polychlorodibenzo-p-dioxin	MeSH
Chlorinated dibenzo p dioxins	MeSH
Chlorinated dibenzo-p-dioxins	MeSH
PCDD	MeSH
Polychlorinated dibenzo-p-dioxins	MeSH
Polychlorodibenzo 4 dioxin	MeSH
Tetrachlorodibenzo-p-dioxin	MeSH
Dibenzo-p-dioxins, chlorinated	MeSH
Polychlorinated dibenzo p dioxins	MeSH

Chemical Formula

C₁₂H₄Cl₄O₂

Average Molecular Weight

321.971

Monoisotopic Molecular Weight

319.8965402

IUPAC Name

2,3,7,8-tetrachlorooxanthrene

Traditional Name

dioxin

CAS Registry Number

Not Available

SMILES

[H]C1=C2OC3=C([H])C(Cl)=C(Cl)C([H])=C3OC2=C([H])C(Cl)=C1Cl

InChI Identifier

InChI=1S/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H

InChI Key

HGUFODBRKLSHSI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorinated dibenzo-p-dioxins. These are organic compounds containing a chlorine atom attached to a dibenzo-p-dioxin moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxins

Sub Class

Benzo-p-dioxins

Direct Parent

Chlorinated dibenzo-p-dioxins

Alternative Parents

Substituents

Chlorinated-dibenzo-p-dioxin
Diaryl ether
Benzenoid
Aryl halide
Aryl chloride
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polychlorinated dibenzodioxine (CHEBI:28119 )
PCDDs (C07557 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Microsome (HMDB: HMDB0258755)
Membrane (HMDB: HMDB0258755)
Membrane (HMDB: HMDB0258755)
Membrane (HMDB: HMDB0258755)
Nuclear membrane (HMDB: HMDB0258755)
Cell surface (HMDB: HMDB0258755)
Nucleolus (HMDB: HMDB0258755)
Extracellular matrix (HMDB: HMDB0258755)
Microtubule (HMDB: HMDB0258755)
Secretory granule (HMDB: HMDB0258755)
Nucleus matrix (HMDB: HMDB0258755)
Microtubule (HMDB: HMDB0258755)
Centrosome (HMDB: HMDB0258755)
Basolateral cell membrane (HMDB: HMDB0258755)
Actin filament (HMDB: HMDB0258755)
Extracellular (HMDB: HMDB0258755)
Cytosol (HMDB: HMDB0258755)
Cell junction (HMDB: HMDB0258755)
Focal adhesion (HMDB: HMDB0258755)

Organelle

Smooth endoplasmic reticulum

Sarcoplasmic reticulum (HMDB: HMDB0258755)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (HMDB: HMDB0258755)

Biochemical process

Endocytosis (HMDB: HMDB0258755)
Cell cycle (HMDB: HMDB0258755)

Biochemical pathway

Metabolic pathway

Oxidative Phosphorylation (HMDB: HMDB0258755)
Fatty Acid Metabolism (HMDB: HMDB0258755)
Insulin secretion (HMDB: HMDB0258755)
Arachidonic Acid Metabolism (HMDB: HMDB0258755)
Inositol Phosphate Metabolism (HMDB: HMDB0258755)
Nitrogen Metabolism (HMDB: HMDB0258755)
Oxidative Phosphorylation (HMDB: HMDB0258755)

Protein pathway

Proteasome (HMDB: HMDB0258755)

Physiological pathway

Long-term potentiation (HMDB: HMDB0258755)
Circadian rhythm (HMDB: HMDB0258755)
Axon guidance (HMDB: HMDB0258755)

RNA polymerase (HMDB: HMDB0258755)
Insulin signaling pathway (HMDB: HMDB0258755)

Signaling pathway

Wnt signaling pathway (HMDB: HMDB0258755)

Eicosanoids (HMDB: HMDB0258755)
Phenothiazines (HMDB: HMDB0258755)
Ovarian Steroidogenesis (HMDB: HMDB0258755)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.59	ALOGPS
logP	5.42	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.7 m³·mol⁻¹	ChemAxon
Polarizability	28.72 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	166.509	30932474
DeepCCS	[M-H]-	164.151	30932474
DeepCCS	[M-2H]-	198.178	30932474
DeepCCS	[M+Na]+	173.186	30932474
AllCCS	[M+H]+	158.5	32859911
AllCCS	[M+H-H2O]+	155.1	32859911
AllCCS	[M+NH4]+	161.6	32859911
AllCCS	[M+Na]+	162.5	32859911
AllCCS	[M-H]-	138.5	32859911
AllCCS	[M+Na-2H]-	137.2	32859911
AllCCS	[M+HCOO]-	135.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3,7,8-Tetrachlorodibenzo-p-dioxin	[H]C1=C2OC3=C([H])C(Cl)=C(Cl)C([H])=C3OC2=C([H])C(Cl)=C1Cl	3162.4	Standard polar	33892256
2,3,7,8-Tetrachlorodibenzo-p-dioxin	[H]C1=C2OC3=C([H])C(Cl)=C(Cl)C([H])=C3OC2=C([H])C(Cl)=C1Cl	2488.0	Standard non polar	33892256
2,3,7,8-Tetrachlorodibenzo-p-dioxin	[H]C1=C2OC3=C([H])C(Cl)=C(Cl)C([H])=C3OC2=C([H])C(Cl)=C1Cl	2458.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3,7,8-Tetrachlorodibenzo-p-dioxin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0019000000-a92e0ba0967da6d02f55	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3,7,8-Tetrachlorodibenzo-p-dioxin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-1229000000-9fb7d8887dd33f8aec9c	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,7,8-Tetrachlorodibenzo-p-dioxin 10V, Positive-QTOF	splash10-00di-0009000000-6d8afb28fd8cfc121565	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,7,8-Tetrachlorodibenzo-p-dioxin 20V, Positive-QTOF	splash10-00di-0009000000-6d8afb28fd8cfc121565	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,7,8-Tetrachlorodibenzo-p-dioxin 40V, Positive-QTOF	splash10-00di-0009000000-6d8afb28fd8cfc121565	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,7,8-Tetrachlorodibenzo-p-dioxin 10V, Negative-QTOF	splash10-014i-0009000000-733090941a128654f2c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,7,8-Tetrachlorodibenzo-p-dioxin 20V, Negative-QTOF	splash10-014i-0009000000-733090941a128654f2c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,7,8-Tetrachlorodibenzo-p-dioxin 40V, Negative-QTOF	splash10-014i-2039000000-f39fc6f94e7a83e4d1a9	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14865

KEGG Compound ID

C07557

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,3,7,8-Tetrachlorodibenzo-P-Dioxin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28119

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2,3,7,8-Tetrachlorodibenzo-p-dioxin (HMDB0258755)

MOL for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

3D MOL for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

3D SDF for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

3D-SDF for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

PDB for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

3D PDB for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

SMILES for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

INCHI for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

Structure for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

3D Structure for HMDB0258755 (2,3,7,8-Tetrachlorodibenzo-p-dioxin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra