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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 04:36:01 UTC

Update Date

2023-02-21 17:31:01 UTC

HMDB ID

HMDB0062590

Secondary Accession Numbers

HMDB62590

Metabolite 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 View Stereo Labels

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 Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

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

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 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.4 g/l	ALOGPS
LogP	0.77	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.002	31661259
DarkChem	[M-H]-	133.075	31661259
DeepCCS	[M+H]+	133.027	30932474
DeepCCS	[M-H]-	130.024	30932474
DeepCCS	[M-2H]-	166.767	30932474
DeepCCS	[M+Na]+	142.28	30932474
AllCCS	[M+H]+	135.7	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	139.8	32859911
AllCCS	[M+Na]+	141.0	32859911
AllCCS	[M-H]-	133.4	32859911
AllCCS	[M+Na-2H]-	134.4	32859911
AllCCS	[M+HCOO]-	135.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tropate	OCC(C(O)=O)C1=CC=CC=C1	2909.8	Standard polar	33892256
Tropate	OCC(C(O)=O)C1=CC=CC=C1	1528.9	Standard non polar	33892256
Tropate	OCC(C(O)=O)C1=CC=CC=C1	1551.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tropate,1TMS,isomer #1	C[Si](C)(C)OCC(C(=O)O)C1=CC=CC=C1	1548.6	Semi standard non polar	33892256
Tropate,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(CO)C1=CC=CC=C1	1509.0	Semi standard non polar	33892256
Tropate,2TMS,isomer #1	C[Si](C)(C)OCC(C(=O)O[Si](C)(C)C)C1=CC=CC=C1	1551.6	Semi standard non polar	33892256
Tropate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(=O)O)C1=CC=CC=C1	1771.6	Semi standard non polar	33892256
Tropate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CO)C1=CC=CC=C1	1739.0	Semi standard non polar	33892256
Tropate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2025.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Tropate GC-MS (2 TMS)	splash10-0uxr-2910000000-eb03fe76d8f5d3a25cd9	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tropate EI-B (Non-derivatized)	splash10-000l-4900000000-407edf8571758c0b7bb3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tropate GC-EI-TOF (Non-derivatized)	splash10-0uxs-1900000000-1d90642eb8f8a6b95f7e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tropate GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-7900000000-712333c0cffa31fde47d	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tropate GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9550000000-bef23817aef036613937	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tropate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tropate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOF	splash10-014i-0900000000-0707a13c8d1b580bfed2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOF	splash10-0udi-1900000000-cf3d140f67eaa24f0ccb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOF	splash10-0udj-7900000000-495c56f61b6681befef5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOF	splash10-004i-9100000000-a3bdb4b9197c51570d26	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tropate LC-ESI-QQ , negative-QTOF	splash10-00fr-9000000000-d651eae7756be6dbd3b7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tropate 35V, Negative-QTOF	splash10-0udi-0900000000-b40496fe0532c0dc6501	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tropate 10V, Negative-QTOF	splash10-0f6t-1900000000-09033180923f2bc6a362	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tropate 40V, Negative-QTOF	splash10-0uk9-9800000000-37cd43edd217360aa619	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tropate 20V, Negative-QTOF	splash10-0uk9-5900000000-56d98b6a74f8cd25523d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 10V, Positive-QTOF	splash10-00kb-0900000000-1d6ce743efa443e904c3	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 20V, Positive-QTOF	splash10-0f6t-1900000000-0491733b8847718c0161	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 40V, Positive-QTOF	splash10-0udi-1900000000-1c49c3ec65489e3596b7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 10V, Negative-QTOF	splash10-01b9-0900000000-3acc80a51dbeed08aaaf	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 20V, Negative-QTOF	splash10-0fki-2900000000-4ec0b26cc564e5fb8354	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 40V, Negative-QTOF	splash10-004i-9600000000-555eba6b223be82ecb55	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 10V, Positive-QTOF	splash10-0006-9700000000-89815cc2afd2db7e5641	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 20V, Positive-QTOF	splash10-0006-9300000000-3925d31aa65d95b127de	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 40V, Positive-QTOF	splash10-002f-9400000000-45ddc7b042eeacc21902	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 10V, Negative-QTOF	splash10-0udi-0900000000-0434a9c3339fe91ab3be	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 20V, Negative-QTOF	splash10-0udi-4900000000-e0ce022c773703d9051b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tropate 40V, Negative-QTOF	splash10-0udi-5900000000-831d6fcf7a77545b7de7	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

C00035885

Chemspider ID

Not Available

KEGG Compound ID

C01456

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

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. Sulfotransferase family cytosolic 2B member 1

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 acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

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 acid	details
Tropate → 3,4,5-trihydroxy-6-[(3-hydroxy-2-phenylpropanoyl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for Tropate (HMDB0062590)

MOL for HMDB0062590 (Tropate)

3D MOL for HMDB0062590 (Tropate)

3D SDF for HMDB0062590 (Tropate)

3D-SDF for HMDB0062590 (Tropate)

PDB for HMDB0062590 (Tropate)

3D PDB for HMDB0062590 (Tropate)

SMILES for HMDB0062590 (Tropate)

INCHI for HMDB0062590 (Tropate)

Structure for HMDB0062590 (Tropate)

3D Structure for HMDB0062590 (Tropate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions