Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:12:20 UTC

Update Date

2021-09-26 23:06:48 UTC

HMDB ID

HMDB0253528

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Iodoform

Description

Iodoform, also known as carbon triiodide or CHI3, belongs to the class of organic compounds known as trihalomethanes. These are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms. Around the beginning of the 20th century, it was used in medicine as a healing and antiseptic dressing for wounds and sores, although this use is now superseded by superior antiseptics. Also conversion to carbon dioxide is possible: Iodoform reacts with aqueous silver nitrate to produce carbon monoxide. It is the active ingredient in many ear powders for dogs and cats, along with zinc oxide and propanoic acid, which are used to prevent infection and facilitate removal of ear hair. The reaction of iodine and base with methyl ketones is so reliable that the iodoform test (the appearance of a yellow precipitate) is used to probe the presence of a methyl ketone. The synthesis of iodoform was first described by Georges-Simon Serullas in 1822, by reactions of iodine vapour with steam over red-hot coals, and also by reaction of potassium with ethanolic iodine in the presence of water; and at much the same time independently by John Thomas Cooper. Upon heating iodoform decomposes to produce diatomic iodine, hydrogen iodide gas, and carbon. Iodoform is possibly neutral. The molecule adopts tetrahedral molecular geometry with C3v symmetry. Some reagents (e.g. hydrogen iodide) convert iodoform to diiodomethane. The angel's bonnet mushroom contains iodoform, and shows its characteristic odor. This compound has been identified in human blood as reported by (PMID: 31557052 ). Iodoform is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Iodoform 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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Carbon triiodide	ChEBI
CHI3	ChEBI
Jodoform	ChEBI
Triiodomethane	ChEBI
Tri-iodomethane	MeSH

Chemical Formula

CHI₃

Average Molecular Weight

393.732

Monoisotopic Molecular Weight

393.72124

IUPAC Name

triiodomethane

Traditional Name

iodoform

CAS Registry Number

Not Available

SMILES

IC(I)I

InChI Identifier

InChI=1S/CHI3/c2-1(3)4/h1H

InChI Key

OKJPEAGHQZHRQV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihalomethanes. These are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Alkyl halides

Sub Class

Halomethanes

Direct Parent

Trihalomethanes

Alternative Parents

Substituents

Trihalomethane
Hydrocarbon derivative
Organoiodide
Alkyl iodide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:37758 )
iodomethanes (CHEBI:37758 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0253528)

Process

Not Available

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	2.82	ALOGPS
logP	4.65	ChemAxon
logS	-3.4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.24 m³·mol⁻¹	ChemAxon
Polarizability	17.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	143.756	30932474
DeepCCS	[M-H]-	141.156	30932474
DeepCCS	[M-2H]-	177.406	30932474
DeepCCS	[M+Na]+	152.638	30932474
AllCCS	[M+H]+	140.6	32859911
AllCCS	[M+H-H2O]+	138.3	32859911
AllCCS	[M+NH4]+	142.8	32859911
AllCCS	[M+Na]+	143.4	32859911
AllCCS	[M-H]-	263.3	32859911
AllCCS	[M+Na-2H]-	270.2	32859911
AllCCS	[M+HCOO]-	277.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Iodoform	IC(I)I	2026.1	Standard polar	33892256
Iodoform	IC(I)I	1182.2	Standard non polar	33892256
Iodoform	IC(I)I	1393.4	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 - Iodoform GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-0059000000-0481ae697383bce56154	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iodoform GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 10V, Positive-QTOF	splash10-0006-0009000000-16f29df8509b8f02e7d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 20V, Positive-QTOF	splash10-0006-0009000000-16f29df8509b8f02e7d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 40V, Positive-QTOF	splash10-0006-0009000000-16f29df8509b8f02e7d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 10V, Negative-QTOF	splash10-0006-0009000000-5bda4f898f1b084632a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 20V, Negative-QTOF	splash10-0006-0009000000-5bda4f898f1b084632a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 40V, Negative-QTOF	splash10-0006-0009000000-5bda4f898f1b084632a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 10V, Positive-QTOF	splash10-0006-0009000000-7725b56fa97247a1692e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 20V, Positive-QTOF	splash10-0006-0009000000-7725b56fa97247a1692e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 40V, Positive-QTOF	splash10-014i-0090000000-d9c86305c239ff99fda1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 10V, Negative-QTOF	splash10-0006-0009000000-19ab66d24bb02d3f5bfb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 20V, Negative-QTOF	splash10-0006-0009000000-19ab66d24bb02d3f5bfb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iodoform 40V, Negative-QTOF	splash10-0006-0009000000-19ab66d24bb02d3f5bfb	2021-10-12	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

DB13813

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C13383

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Iodoform

METLIN ID

Not Available

PubChem Compound

6374

PDB ID

Not Available

ChEBI ID

37758

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 Iodoform (HMDB0253528)

MOL for HMDB0253528 (Iodoform)

3D MOL for HMDB0253528 (Iodoform)

3D SDF for HMDB0253528 (Iodoform)

3D-SDF for HMDB0253528 (Iodoform)

PDB for HMDB0253528 (Iodoform)

3D PDB for HMDB0253528 (Iodoform)

SMILES for HMDB0253528 (Iodoform)

INCHI for HMDB0253528 (Iodoform)

Structure for HMDB0253528 (Iodoform)

3D Structure for HMDB0253528 (Iodoform)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra