NP-MRD: Showing NP-Card for Tropate (NP0001146)

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Record Information

Version

1.0

Created at

2017-03-23 04:36:01 UTC

Updated at

2021-10-07 20:38:23 UTC

NP-MRD ID

NP0001146

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tropate

Description

Tropate, 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

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

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    8   10                                                       
CONECT    7    4    5    8                                                  
CONECT    8    6    7    9                                                  
CONECT    9    8   11   12                                                  
CONECT   10    6                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments

Synonyms

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

Chemical Formula

C₉H₁₀O₃

Average Mass

166.1739 Da

Monoisotopic Mass

166.06299 Da

IUPAC Name

3-hydroxy-2-phenylpropanoic acid

Traditional Name

(+-)-tropic acid

CAS Registry Number

552-63-6

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 Key

JACRWUWPXAESPB-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Datura stamonium	KNApSAcK Database	22123792
Datura stramonium	LOTUS Database	35616633
Hyoscyamus muticus	LOTUS Database	35616633
Mandragora autumnalis	KNApSAcK Database	22123792
Mandragora officinarum	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Secale cereale	LOTUS Database	35616633

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

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	118.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	322.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	10.4 g/l	Tetko, 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/)
LogP	0.77	Tetko, 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

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0062590

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tropic_acid

METLIN ID

Not Available

PubChem Compound

10726

PDB ID

Not Available

ChEBI ID

30765

Good Scents ID

rw1295751

References

General References

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 ]
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 ]
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 ]
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 ]
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 ]

Showing NP-Card for Tropate (NP0001146)

MOL for NP0001146 (Tropate)

3D MOL for NP0001146 (Tropate)

3D SDF for NP0001146 (Tropate)

3D-SDF for NP0001146 (Tropate)

PDB for NP0001146 (Tropate)

3D PDB for NP0001146 (Tropate)

SMILES for NP0001146 (Tropate)

INCHI for NP0001146 (Tropate)

Structure for NP0001146 (Tropate)

3D Structure for NP0001146 (Tropate)