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Showing metabocard for Iodoform (HMDB0253528)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 12:12:20 UTC
Update Date2021-09-26 23:06:48 UTC
HMDB IDHMDB0253528
Secondary Accession NumbersNone
Metabolite Identification
Common NameIodoform
DescriptionIodoform, 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century, it was used in medicine as a healing and antiseptic dressing for wounds and sores, although this use is now superseded by superior antiseptics.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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0253528 (Iodoform)


  Mrv1533004251513232D          

  4  3  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
M  END
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3D MOL for HMDB0253528 (Iodoform)

HMDB0253528
     RDKit          3D
Iodoform
  5  4  0  0  0  0  0  0  0  0999 V2000
    2.0172   -0.1173   -0.5004 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022    0.0121    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162    1.8065   -0.4979 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -1.6846   -0.5109 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -0.0167    1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
M  END
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3D SDF for HMDB0253528 (Iodoform)


  Mrv1533004251513232D          

  4  3  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253528

> <DATABASE_NAME>
hmdb

> <SMILES>
IC(I)I

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

> <INCHI_KEY>
OKJPEAGHQZHRQV-UHFFFAOYSA-N

> <FORMULA>
CHI3

> <MOLECULAR_WEIGHT>
393.732

> <EXACT_MASS>
393.72124

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
17.59072069267678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
triiodomethane

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
4.647148779999999

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
45.24229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iodoform

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0253528 (Iodoform)

HMDB0253528
     RDKit          3D
Iodoform
  5  4  0  0  0  0  0  0  0  0999 V2000
    2.0172   -0.1173   -0.5004 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022    0.0121    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162    1.8065   -0.4979 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -1.6846   -0.5109 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -0.0167    1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
M  END
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PDB for HMDB0253528 (Iodoform)

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  I   UNK     0       2.310   1.334   0.000  0.00  0.00           I+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  I   UNK     0       2.310  -1.334   0.000  0.00  0.00           I+0
HETATM    4  I   UNK     0       0.000   0.000   0.000  0.00  0.00           I+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0253528 (Iodoform)

COMPND    HMDB0253528
HETATM    1  I1  UNL     1       2.017  -0.117  -0.500  1.00  0.00           I  
HETATM    2  C1  UNL     1      -0.002   0.012   0.200  1.00  0.00           C  
HETATM    3  I2  UNL     1      -0.916   1.806  -0.498  1.00  0.00           I  
HETATM    4  I3  UNL     1      -1.095  -1.685  -0.511  1.00  0.00           I  
HETATM    5  H1  UNL     1      -0.004  -0.017   1.309  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    4    5
END
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SMILES for HMDB0253528 (Iodoform)

IC(I)I
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INCHI for HMDB0253528 (Iodoform)

InChI=1S/CHI3/c2-1(3)4/h1H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Carbon triiodideChEBI
CHI3ChEBI
JodoformChEBI
TriiodomethaneChEBI
Tri-iodomethaneMeSH
Chemical FormulaCHI3
Average Molecular Weight393.732
Monoisotopic Molecular Weight393.72124
IUPAC Nametriiodomethane
Traditional Nameiodoform
CAS Registry NumberNot Available
SMILES
IC(I)I
InChI Identifier
InChI=1S/CHI3/c2-1(3)4/h1H
InChI KeyOKJPEAGHQZHRQV-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.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassHalomethanes
Direct ParentTrihalomethanes
Alternative Parents
Substituents
  • Trihalomethane
  • Hydrocarbon derivative
  • Organoiodide
  • Alkyl iodide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.82ALOGPS
logP4.65ChemAxon
logS-3.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.24 m³·mol⁻¹ChemAxon
Polarizability17.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+143.75630932474
DeepCCS[M-H]-141.15630932474
DeepCCS[M-2H]-177.40630932474
DeepCCS[M+Na]+152.63830932474
AllCCS[M+H]+140.632859911
AllCCS[M+H-H2O]+138.332859911
AllCCS[M+NH4]+142.832859911
AllCCS[M+Na]+143.432859911
AllCCS[M-H]-263.332859911
AllCCS[M+Na-2H]-270.232859911
AllCCS[M+HCOO]-277.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202210.6901 minutes33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1207.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid522.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid224.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid410.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid259.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid408.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid508.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)624.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid869.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid305.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid956.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid357.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid405.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate731.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA463.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water256.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IodoformIC(I)I2026.1Standard polar33892256
IodoformIC(I)I1182.2Standard non polar33892256
IodoformIC(I)I1393.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Iodoform GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0059000000-0481ae697383bce561542021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iodoform GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 10V, Positive-QTOFsplash10-0006-0009000000-16f29df8509b8f02e7d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 20V, Positive-QTOFsplash10-0006-0009000000-16f29df8509b8f02e7d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 40V, Positive-QTOFsplash10-0006-0009000000-16f29df8509b8f02e7d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 10V, Negative-QTOFsplash10-0006-0009000000-5bda4f898f1b084632a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 20V, Negative-QTOFsplash10-0006-0009000000-5bda4f898f1b084632a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 40V, Negative-QTOFsplash10-0006-0009000000-5bda4f898f1b084632a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 10V, Positive-QTOFsplash10-0006-0009000000-7725b56fa97247a1692e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 20V, Positive-QTOFsplash10-0006-0009000000-7725b56fa97247a1692e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 40V, Positive-QTOFsplash10-014i-0090000000-d9c86305c239ff99fda12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 10V, Negative-QTOFsplash10-0006-0009000000-19ab66d24bb02d3f5bfb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 20V, Negative-QTOFsplash10-0006-0009000000-19ab66d24bb02d3f5bfb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iodoform 40V, Negative-QTOFsplash10-0006-0009000000-19ab66d24bb02d3f5bfb2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13813
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC13383
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIodoform
METLIN IDNot Available
PubChem Compound6374
PDB IDNot Available
ChEBI ID37758
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]