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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:05:50 UTC

Update Date

2021-09-26 22:54:54 UTC

HMDB ID

HMDB0246057

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,5-Diiodosalicylic acid

Description

3,5-Diiodosalicylic acid, also known as lithium diiodosalicylate or 2-hydroxy-3,5-diiodobenzoate, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. Based on a literature review very few articles have been published on 3,5-Diiodosalicylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,5-diiodosalicylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,5-Diiodosalicylic acid 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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  I   UNK     0      -1.334  -0.770   0.000  0.00  0.00           I+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  I   UNK     0       1.334   3.850   0.000  0.00  0.00           I+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5-Diiodosalicylate	Generator
2-HYDROXY-3,5-diiodobenzoate	HMDB
3,5-Diiodosalicylic acid, monolithium salt	HMDB
Lithium diiodosalicylate	HMDB
3,5-Diiodosalicylic acid, disodium salt	HMDB
3,5-Diiodosalicylic acid, lithium salt	HMDB
3,5-Diiodosalicylic acid, monosodium salt	HMDB
Lithium di-iodosalicylate	HMDB
Lithium diiodosalicilate	HMDB

Chemical Formula

C₇H₄I₂O₃

Average Molecular Weight

389.9138

Monoisotopic Molecular Weight

389.824980834

IUPAC Name

2-hydroxy-3,5-diiodobenzoic acid

Traditional Name

3,5-diiodosalicylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(O)C(I)=CC(I)=C1

InChI Identifier

InChI=1S/C7H4I2O3/c8-3-1-4(7(11)12)6(10)5(9)2-3/h1-2,10H,(H,11,12)

InChI Key

DHZVWQPHNWDCFS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acids

Alternative Parents

Substituents

Salicylic acid
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
3-halobenzoic acid
Halobenzoic acid
Benzoic acid
4-halophenol
2-iodophenol
2-halophenol
4-iodophenol
Benzoyl
Iodobenzene
Phenol
Halobenzene
Aryl iodide
Aryl halide
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organoiodide
Organohalogen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	3.13	ALOGPS
logP	3.84	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.51	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.02 m³·mol⁻¹	ChemAxon
Polarizability	23.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	154.84	30932474
DeepCCS	[M-H]-	152.356	30932474
DeepCCS	[M-2H]-	187.841	30932474
DeepCCS	[M+Na]+	162.441	30932474
AllCCS	[M+H]+	170.2	32859911
AllCCS	[M+H-H2O]+	166.9	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	150.9	32859911
AllCCS	[M+Na-2H]-	152.7	32859911
AllCCS	[M+HCOO]-	154.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.9695 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.1 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1578.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	448.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	133.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	302.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	582.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	708.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	692.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	936.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	420.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1379.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	496.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	873.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	316.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	315.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Diiodosalicylic acid	OC(=O)C1=C(O)C(I)=CC(I)=C1	3222.3	Standard polar	33892256
3,5-Diiodosalicylic acid	OC(=O)C1=C(O)C(I)=CC(I)=C1	2126.2	Standard non polar	33892256
3,5-Diiodosalicylic acid	OC(=O)C1=C(O)C(I)=CC(I)=C1	2067.1	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 - 3,5-Diiodosalicylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-0019000000-549b5f3af86fddfe3b42	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodosalicylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodosalicylic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodosalicylic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodosalicylic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodosalicylic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodosalicylic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diiodosalicylic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - 3,5-Diiodosalicylic acid 10V, Positive-QTOF	splash10-0006-0009000000-28df5e08967422c39900	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 20V, Positive-QTOF	splash10-00dl-0009000000-17b1d76d0781933a3d1d	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 40V, Positive-QTOF	splash10-00xr-0009000000-75c3dc4eeb15ad5907ae	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 10V, Negative-QTOF	splash10-000l-0009000000-20d8f6db3a19ffeb0910	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 20V, Negative-QTOF	splash10-0006-0009000000-2348bc4c6665dd998044	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 40V, Negative-QTOF	splash10-0006-0109000000-e0867640df2781e698be	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 10V, Positive-QTOF	splash10-00di-0009000000-608594d2711e782a277f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 20V, Positive-QTOF	splash10-00di-0009000000-7bc5e5a27ccdfe1a7fad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 40V, Positive-QTOF	splash10-00dl-0239000000-2977d48623fd6e01ca83	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 10V, Negative-QTOF	splash10-000l-0009000000-612fc5621eb81d97b929	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 20V, Negative-QTOF	splash10-0006-0009000000-263a52f1c2b8ee3a6d65	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diiodosalicylic acid 40V, Negative-QTOF	splash10-004l-1908000000-1ff089c4ab2657b49d07	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

DB04674

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8310

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8631

PDB ID

Not Available

ChEBI ID

Not Available

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 3,5-Diiodosalicylic acid (HMDB0246057)

MOL for HMDB0246057 (3,5-Diiodosalicylic acid)

3D MOL for HMDB0246057 (3,5-Diiodosalicylic acid)

3D SDF for HMDB0246057 (3,5-Diiodosalicylic acid)

3D-SDF for HMDB0246057 (3,5-Diiodosalicylic acid)

PDB for HMDB0246057 (3,5-Diiodosalicylic acid)

3D PDB for HMDB0246057 (3,5-Diiodosalicylic acid)

SMILES for HMDB0246057 (3,5-Diiodosalicylic acid)

INCHI for HMDB0246057 (3,5-Diiodosalicylic acid)

Structure for HMDB0246057 (3,5-Diiodosalicylic acid)

3D Structure for HMDB0246057 (3,5-Diiodosalicylic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra