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Record Information
Version1.0
Created at2017-03-23 04:36:01 UTC
Updated at2021-10-07 20:38:23 UTC
NP-MRD IDNP0001146
Secondary Accession NumbersNone
Natural Product 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
Thumb
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 Mass166.1739 Da
Monoisotopic Mass166.06299 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Datura stamoniumKNApSAcK Database
Datura stramoniumLOTUS Database
Hyoscyamus muticusLOTUS Database
Mandragora autumnalisKNApSAcK Database
Mandragora officinarumLOTUS Database
Panax ginsengLOTUS Database
Secale cerealeLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point118.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point322.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility10.4 g/lTetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., Palyulin, V.A., Radchenko, E.V., Zefirov, N.S., Makarenko, A.S., Tanchuk, V.Y. & Prokopenko, V. V. (2005). Virtual computational chemistry laboratory-design and description. Journal of computer-aided molecular design, 19(6), 453-463. (http://www.vcclab.org/lab/alogps/)
LogP0.77Tetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., Palyulin, V.A., Radchenko, E.V., Zefirov, N.S., Makarenko, A.S., Tanchuk, V.Y. & Prokopenko, V. V. (2005). Virtual computational chemistry laboratory-design and description. Journal of computer-aided molecular design, 19(6), 453-463. (http://www.vcclab.org/lab/alogps/)
Predicted Properties
PropertyValueSource
logP0.77ALOGPS
logP0.87ChemAxon
logS-1.2ALOGPS
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
HMDB IDHMDB0062590
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB098134
KNApSAcK IDC00035885
Chemspider ID10274
KEGG Compound IDC01456
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTropic_acid
METLIN IDNot Available
PubChem Compound10726
PDB IDNot Available
ChEBI ID30765
Good Scents IDrw1295751
References
General References
  1. Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666 ]
  2. Wada S, Yoshimitsu T, Koga N, Yamada H, Oguri K, Yoshimura H: Metabolism in vivo of the tropane alkaloid, scopolamine, in several mammalian species. Xenobiotica. 1991 Oct;21(10):1289-300. doi: 10.3109/00498259109043204. [PubMed:1796606 ]
  3. Scott DK, Neville K, Garg U: Determination of hydroxyurea in serum or plasma using gas chromatography-mass spectrometry (GC-MS). Methods Mol Biol. 2010;603:279-87. doi: 10.1007/978-1-60761-459-3_26. [PubMed:20077079 ]
  4. Zimmermann T, Dimmel A, Juttemeyer S, Springer D, Loch M: Rapid resolution liquid chromatography for monitoring the quality of stockpiled atropine preparations for injection. Drug Test Anal. 2012 Mar-Apr;4(3-4):222-8. doi: 10.1002/dta.402. [PubMed:22467254 ]
  5. Trnavska Z, Verner P: Binding of indomethacin ester with tropic acid to human serum albumin. Pharmacology. 1983;26(5):270-3. doi: 10.1159/000137810. [PubMed:6856668 ]