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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 04:36:01 UTC
Update Date2021-09-14 15:44:54 UTC
HMDB IDHMDB0062590
Secondary Accession Numbers
  • HMDB62590
Metabolite Identification
Common NameTropate
DescriptionTropate, also known as Tropic acid or alpha-(Hydroxymethyl)phenylacetic acid, is classified as a beta hydroxy acid or a Beta hydroxy acid derivative. Beta hydroxy acids are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Tropate is considered to be soluble in water and acidic. Tropate can be synthesized from hydratropic acid and propionic acid. Tropate can be synthesized into tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate
Structure
Data?1563866333
Synonyms
ValueSource
(+-)-Tropic acidChEBI
2-Phenylhydracrylic acidChEBI
3-Hydroxy-2-phenylpropionic acidChEBI
alpha-(Hydroxymethyl)benzeneacetic acidChEBI
alpha-(Hydroxymethyl)phenylacetic acidChEBI
alpha-Phenyl-beta-hydroxypropionic acidChEBI
beta-Hydroxyhydratropic acidChEBI
Tropic acidKegg
(+-)-TropateGenerator
2-PhenylhydracrylateGenerator
3-Hydroxy-2-phenylpropionateGenerator
a-(Hydroxymethyl)benzeneacetateGenerator
a-(Hydroxymethyl)benzeneacetic acidGenerator
alpha-(Hydroxymethyl)benzeneacetateGenerator
Α-(hydroxymethyl)benzeneacetateGenerator
Α-(hydroxymethyl)benzeneacetic acidGenerator
a-(Hydroxymethyl)phenylacetateGenerator
a-(Hydroxymethyl)phenylacetic acidGenerator
alpha-(Hydroxymethyl)phenylacetateGenerator
Α-(hydroxymethyl)phenylacetateGenerator
Α-(hydroxymethyl)phenylacetic acidGenerator
a-Phenyl-b-hydroxypropionateGenerator
a-Phenyl-b-hydroxypropionic acidGenerator
alpha-Phenyl-beta-hydroxypropionateGenerator
Α-phenyl-β-hydroxypropionateGenerator
Α-phenyl-β-hydroxypropionic acidGenerator
b-HydroxyhydratropateGenerator
b-Hydroxyhydratropic acidGenerator
beta-HydroxyhydratropateGenerator
Β-hydroxyhydratropateGenerator
Β-hydroxyhydratropic acidGenerator
Tropic acid, monosodium saltHMDB
alpha-Phenylhydracrylic acidHMDB
Tropic acid, (+-)-isomerHMDB
Tropic acid, (S)-isomerHMDB
Tropic acid, (R)-isomerHMDB
TropateGenerator
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name3-hydroxy-2-phenylpropanoic acid
Traditional Name(+-)-tropic acid
CAS Registry Number552-63-6
SMILES
OCC(C(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O3/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
InChI KeyJACRWUWPXAESPB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.4 g/lALOGPS
LogP0.77ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(0.77) g/LALOGPS
logP10(0.87) g/LChemAxon
logS10(-1.2) g/LALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.71 m³·mol⁻¹ChemAxon
Polarizability16.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.00231661259
DarkChem[M-H]-133.07531661259
DeepCCS[M+H]+133.02730932474
DeepCCS[M-H]-130.02430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TropateOCC(C(O)=O)C1=CC=CC=C12909.8Standard polar33892256
TropateOCC(C(O)=O)C1=CC=CC=C11528.9Standard non polar33892256
TropateOCC(C(O)=O)C1=CC=CC=C11551.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tropate,1TMS,isomer #1C[Si](C)(C)OCC(C(=O)O)C1=CC=CC=C11548.6Semi standard non polar33892256
Tropate,1TMS,isomer #2C[Si](C)(C)OC(=O)C(CO)C1=CC=CC=C11509.0Semi standard non polar33892256
Tropate,2TMS,isomer #1C[Si](C)(C)OCC(C(=O)O[Si](C)(C)C)C1=CC=CC=C11551.6Semi standard non polar33892256
Tropate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(C(=O)O)C1=CC=CC=C11771.6Semi standard non polar33892256
Tropate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CO)C1=CC=CC=C11739.0Semi standard non polar33892256
Tropate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12025.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tropate GC-MS (2 TMS)splash10-0uxr-2910000000-eb03fe76d8f5d3a25cd92014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tropate EI-B (Non-derivatized)splash10-000l-4900000000-407edf8571758c0b7bb32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tropate GC-EI-TOF (Non-derivatized)splash10-0uxs-1900000000-1d90642eb8f8a6b95f7e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tropate GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-7900000000-712333c0cffa31fde47d2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tropate GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9550000000-bef23817aef0366139372017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tropate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tropate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-0707a13c8d1b580bfed22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOFsplash10-0udi-1900000000-cf3d140f67eaa24f0ccb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOFsplash10-0udj-7900000000-495c56f61b6681befef52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOFsplash10-004i-9100000000-a3bdb4b9197c51570d262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOFsplash10-00fr-9000000000-d651eae7756be6dbd3b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropate 35V, Negative-QTOFsplash10-0udi-0900000000-b40496fe0532c0dc65012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropate 10V, Negative-QTOFsplash10-0f6t-1900000000-09033180923f2bc6a3622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropate 40V, Negative-QTOFsplash10-0uk9-9800000000-37cd43edd217360aa6192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tropate 20V, Negative-QTOFsplash10-0uk9-5900000000-56d98b6a74f8cd25523d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 10V, Positive-QTOFsplash10-00kb-0900000000-1d6ce743efa443e904c32016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 20V, Positive-QTOFsplash10-0f6t-1900000000-0491733b8847718c01612016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 40V, Positive-QTOFsplash10-0udi-1900000000-1c49c3ec65489e3596b72016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 10V, Negative-QTOFsplash10-01b9-0900000000-3acc80a51dbeed08aaaf2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 20V, Negative-QTOFsplash10-0fki-2900000000-4ec0b26cc564e5fb83542016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 40V, Negative-QTOFsplash10-004i-9600000000-555eba6b223be82ecb552016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 10V, Positive-QTOFsplash10-0006-9700000000-89815cc2afd2db7e56412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 20V, Positive-QTOFsplash10-0006-9300000000-3925d31aa65d95b127de2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 40V, Positive-QTOFsplash10-002f-9400000000-45ddc7b042eeacc219022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 10V, Negative-QTOFsplash10-0udi-0900000000-0434a9c3339fe91ab3be2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 20V, Negative-QTOFsplash10-0udi-4900000000-e0ce022c773703d9051b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tropate 40V, Negative-QTOFsplash10-0udi-5900000000-831d6fcf7a77545b7de72021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00035885
Chemspider IDNot Available
KEGG Compound IDC01456
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTropic_acid
METLIN IDNot Available
PubChem Compound10726
PDB IDNot Available
ChEBI ID30765
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 ReferencesNot Available

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Tropate → 2-phenyl-3-(sulfooxy)propanoic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Tropate → 6-(2-carboxy-2-phenylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Tropate → 3,4,5-trihydroxy-6-[(3-hydroxy-2-phenylpropanoyl)oxy]oxane-2-carboxylic aciddetails