Tropic acid (YMDB02309)

Identification

YMDB ID

YMDB02309

Name

Tropic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Tropate, also known as (+-)-tropic acid or (+-)-tropate, 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. Tropate is an extremely weak basic (essentially neutral) compound (based on its pKa). Tropate exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(+-)-tropic acid
2-phenylhydracrylic acid
3-hydroxy-2-phenylpropionic acid
alpha-(hydroxymethyl)benzeneacetic acid
alpha-(Hydroxymethyl)phenylacetic acid
alpha-phenyl-beta-hydroxypropionic acid
beta-hydroxyhydratropic acid
Tropate
Tropic acid
(+-)-Tropate
2-Phenylhydracrylate
3-Hydroxy-2-phenylpropionate
a-(Hydroxymethyl)benzeneacetate
a-(Hydroxymethyl)benzeneacetic acid
alpha-(Hydroxymethyl)benzeneacetate
Α-(hydroxymethyl)benzeneacetate
Α-(hydroxymethyl)benzeneacetic acid
a-(Hydroxymethyl)phenylacetate
a-(Hydroxymethyl)phenylacetic acid
alpha-(Hydroxymethyl)phenylacetate
Α-(hydroxymethyl)phenylacetate
Α-(hydroxymethyl)phenylacetic acid
a-Phenyl-b-hydroxypropionate
a-Phenyl-b-hydroxypropionic acid
alpha-Phenyl-beta-hydroxypropionate
Α-phenyl-β-hydroxypropionate
Α-phenyl-β-hydroxypropionic acid
b-Hydroxyhydratropate
b-Hydroxyhydratropic acid
beta-Hydroxyhydratropate
Β-hydroxyhydratropate
Β-hydroxyhydratropic acid
Tropic acid, monosodium salt
alpha-Phenylhydracrylic acid
Tropic acid, (+-)-isomer
Tropic acid, (S)-isomer
Tropic acid, (R)-isomer

CAS number

552-63-6

Weight

Average: 166.1739
Monoisotopic: 166.062994186

InChI Key

JACRWUWPXAESPB-UHFFFAOYSA-N

InChI

InChI=1S/C9H10O3/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)

IUPAC Name

3-hydroxy-2-phenylpropanoic acid

Traditional IUPAC Name

(+-)-tropic acid

Chemical Formula

C₉H₁₀O₃

SMILES

OCC(C(O)=O)C1=CC=CC=C1

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

3-hydroxy monocarboxylic acid (CHEBI:30765 )

Physical Properties

State

Solid

Charge

Melting point

118 °C

Experimental Properties

Property	Value	Reference
Water Solubility	20 mg/mL at 25 oC [MERCK INDEX (1996)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	10.4 g/L	ALOGPS
logP	0.77	ALOGPS
logP	0.87	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-2.7	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	3	ChemAxon
Refractivity	43.71 m³·mol⁻¹	ChemAxon
Polarizability	16.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0uxr-2910000000-eb03fe76d8f5d3a25cd9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000l-4900000000-407edf8571758c0b7bb3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxs-1900000000-1d90642eb8f8a6b95f7e	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-7900000000-712333c0cffa31fde47d	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9550000000-bef23817aef036613937	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-0707a13c8d1b580bfed2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-1900000000-cf3d140f67eaa24f0ccb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udj-7900000000-495c56f61b6681befef5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9100000000-a3bdb4b9197c51570d26	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00fr-9000000000-d651eae7756be6dbd3b7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-0900000000-b40496fe0532c0dc6501	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-1900000000-09033180923f2bc6a362	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0uk9-9800000000-37cd43edd217360aa619	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0uk9-5900000000-56d98b6a74f8cd25523d	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0900000000-1d6ce743efa443e904c3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f6t-1900000000-0491733b8847718c0161	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1900000000-1c49c3ec65489e3596b7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-0900000000-3acc80a51dbeed08aaaf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fki-2900000000-4ec0b26cc564e5fb8354	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9600000000-555eba6b223be82ecb55	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9700000000-89815cc2afd2db7e5641	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-3925d31aa65d95b127de	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9400000000-45ddc7b042eeacc21902	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-0434a9c3339fe91ab3be	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-4900000000-e0ce022c773703d9051b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-5900000000-831d6fcf7a77545b7de7	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	30765
HMDB ID	HMDB0062590
Pubchem Compound ID	10726
Kegg ID	C01456
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Tropic_acid
BioCyc ID	Not Available

Structure for #<Compound:0x9cf624ac>