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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-10-30 10:32:48 UTC

Update Date

2022-03-07 03:17:34 UTC

HMDB ID

HMDB0059636

Secondary Accession Numbers

HMDB59636

Metabolite Identification

Common Name

3-(3,5-Diiodo-4-hydroxyphenyl)lactate

Description

3-(3,5-Diiodo-4-hydroxyphenyl)lactate, also known as 3-(4-hydroxy-3,5-diiodophenyl)lactate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-(3,5-diiodo-4-hydroxyphenyl)lactate is part of the Citrate cycle (TCA cycle), Pyruvate metabolism, Glyoxylate and dicarboxylate metabolism, and Proximal tubule bicarbonate reclamation pathways. 3-(3,5-Diiodo-4-hydroxyphenyl)lactate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

  Mrv0541 10301209522D          

 15 15  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 15  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059636

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(CC1=CC(I)=C(O)C(I)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8I2O4/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,12-13H,3H2,(H,14,15)

> <INCHI_KEY>
ZPJHINFPRQWKIH-UHFFFAOYSA-N

> <FORMULA>
C9H8I2O4

> <MOLECULAR_WEIGHT>
433.9664

> <EXACT_MASS>
433.851195584

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.599306807361245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.7388204846666664

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.2552765151140886

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1593470366951166

> <JCHEM_PKA_STRONGEST_BASIC>
-3.83911529963762

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
72.1647

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-OCT-12         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  I   UNK     0       4.001  -0.770   0.000  0.00  0.00           I+0
HETATM   11  I   UNK     0      -1.334  -0.770   0.000  0.00  0.00           I+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    4    5                                                       
CONECT    2    4    6                                                       
CONECT    3    4    7                                                       
CONECT    4    1    2    3                                                  
CONECT    5    1    8   10                                                  
CONECT    6    2    8   11                                                  
CONECT    7    3    9   12                                                  
CONECT    8    5    6   13                                                  
CONECT    9    7   14   15                                                  
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    9                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(3,5-Diiodo-4-hydroxyphenyl)lactic acid	ChEBI
3-(4-Hydroxy-3,5-diiodophenyl)lactate	HMDB
3-(3,5-diiodo-4-Hydroxyphenyl)lactate	ChEBI

Chemical Formula

C₉H₈I₂O₄

Average Molecular Weight

433.9664

Monoisotopic Molecular Weight

433.851195584

IUPAC Name

2-hydroxy-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid

Traditional Name

2-hydroxy-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

OC(CC1=CC(I)=C(O)C(I)=C1)C(O)=O

InChI Identifier

InChI=1S/C9H8I2O4/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,12-13H,3H2,(H,14,15)

InChI Key

ZPJHINFPRQWKIH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
2-halophenol
2-iodophenol
Halobenzene
Iodobenzene
Phenol
Benzenoid
Aryl halide
Aryl iodide
Monocyclic benzene moiety
Hydroxy acid
Alpha-hydroxy acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Carbonyl group
Organic oxide
Organohalogen compound
Organoiodide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organoiodine compound (CHEBI:16122 )
phenols (CHEBI:16122 )
2-hydroxy monocarboxylic acid (CHEBI:16122 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0059636)

Source

Exogenous

Exogenous (HMDB: HMDB0059636)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.48 g/L	ALOGPS
logP	3.08	ALOGPS
logP	2.74	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	2.16	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.16 m³·mol⁻¹	ChemAxon
Polarizability	28.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	165.326	30932474
DeepCCS	[M-H]-	162.579	30932474
DeepCCS	[M-2H]-	198.471	30932474
DeepCCS	[M+Na]+	174.218	30932474
AllCCS	[M+H]+	178.6	32859911
AllCCS	[M+H-H2O]+	175.9	32859911
AllCCS	[M+NH4]+	181.2	32859911
AllCCS	[M+Na]+	181.9	32859911
AllCCS	[M-H]-	166.2	32859911
AllCCS	[M+Na-2H]-	167.7	32859911
AllCCS	[M+HCOO]-	169.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(3,5-Diiodo-4-hydroxyphenyl)lactate	OC(CC1=CC(I)=C(O)C(I)=C1)C(O)=O	3728.4	Standard polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate	OC(CC1=CC(I)=C(O)C(I)=C1)C(O)=O	2449.9	Standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate	OC(CC1=CC(I)=C(O)C(I)=C1)C(O)=O	2457.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,1TMS,isomer #1	C[Si](C)(C)OC(CC1=CC(I)=C(O)C(I)=C1)C(=O)O	2407.0	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,1TMS,isomer #2	C[Si](C)(C)OC1=C(I)C=C(CC(O)C(=O)O)C=C1I	2414.4	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,1TMS,isomer #3	C[Si](C)(C)OC(=O)C(O)CC1=CC(I)=C(O)C(I)=C1	2417.6	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,2TMS,isomer #1	C[Si](C)(C)OC1=C(I)C=C(CC(O[Si](C)(C)C)C(=O)O)C=C1I	2439.7	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(O)C(I)=C1)O[Si](C)(C)C	2405.5	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(O)CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1	2447.6	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC(I)=C(O[Si](C)(C)C)C(I)=C1)O[Si](C)(C)C	2511.1	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CC1=CC(I)=C(O)C(I)=C1)C(=O)O	2677.4	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(I)C=C(CC(O)C(=O)O)C=C1I	2670.6	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC(I)=C(O)C(I)=C1	2673.9	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(I)C=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1I	2938.4	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC(I)=C(O)C(I)=C1)O[Si](C)(C)C(C)(C)C	2889.0	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C1	2942.4	Semi standard non polar	33892256
3-(3,5-Diiodo-4-hydroxyphenyl)lactate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC(I)=C(O[Si](C)(C)C(C)(C)C)C(I)=C1)O[Si](C)(C)C(C)(C)C	3202.3	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-(3,5-Diiodo-4-hydroxyphenyl)lactate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1009100000-230e66a4d981eb024a28	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate GC-MS (3 TMS) - 70eV, Positive	splash10-001i-5000292000-7e6d92d62e490c8a2ae3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 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 - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 10V, Positive-QTOF	splash10-067r-0006900000-59f233a239a46f5b6bd1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 20V, Positive-QTOF	splash10-0apr-0009300000-856a9ebea166c8dcaf88	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 40V, Positive-QTOF	splash10-0560-0009000000-fa04c3a8dd3d13244af0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 10V, Negative-QTOF	splash10-001i-2002900000-c56e106851e263971219	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 20V, Negative-QTOF	splash10-06y9-2009400000-1cfa3e3779fed0fd0a4e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 40V, Negative-QTOF	splash10-0abc-4039000000-1b95595869690aedccf8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 10V, Positive-QTOF	splash10-001i-0002900000-678e018c8603525f5889	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 20V, Positive-QTOF	splash10-05nr-0009500000-f1da6ac578e50d060552	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 40V, Positive-QTOF	splash10-0a4i-0198000000-073b6bab47af9a5e5026	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 10V, Negative-QTOF	splash10-001i-0101900000-70da2ceb640898930e61	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 20V, Negative-QTOF	splash10-004i-2906200000-3772f91b9de247c499f3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,5-Diiodo-4-hydroxyphenyl)lactate 40V, Negative-QTOF	splash10-004i-0900000000-0dba40d354fa6a5575e0	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

KEGG Compound ID

C04367

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440310

PDB ID

Not Available

ChEBI ID

16122

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

Not Available

Enzymes

Enzyme Details

1. Malate dehydrogenase, cytoplasmic

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Not Available
Gene Name:: MDH1
Uniprot ID:: P40925
Molecular weight:: 38627.255

Reactions

3-(3,5-Diiodo-4-hydroxyphenyl)lactate + NAD → 3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate + NADH	details

Showing metabocard for 3-(3,5-Diiodo-4-hydroxyphenyl)lactate (HMDB0059636)

MOL for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

3D MOL for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

3D SDF for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

3D-SDF for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

PDB for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

3D PDB for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

SMILES for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

INCHI for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

Structure for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

3D Structure for HMDB0059636 (3-(3,5-Diiodo-4-hydroxyphenyl)lactate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions