(4S,5S)-5-hydroxy-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid (CED0102379)

Record Information

Version

1.0

Creation Date

2016-06-03 12:47:06 UTC

Update Date

2026-03-31 17:39:01 UTC

SynCED ID

CED0102379

Secondary Accession Numbers

CHEM045040

Identification

Common Name

(4S,5S)-5-hydroxy-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid

Class

Small Molecule

Description

(4S,5S)-5-hydroxy-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This organic acid has the chemical formula C6H10N2O3 and an average molecular weight of 158.16 g/mol. In industrial applications, the compound is used as a pH regulating agent and as a softener and conditioner. It has been recorded in one source, specifically within indoor air, dust, and atmospheric transport. The recorded route of exposure for this substance is inhalation.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(4S,5S)-2-Methyl-4-carboxy-5-hydroxy-3,4,5,6-tetrahydropyrimidine	ChEBI
(4S,5S)-5-HYDROXY-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylIC ACID	ChEBI
(S,S)-2-Methyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid	ChEBI
beta-Hydroxyectoine	ChEBI
Hydroxyectoine	ChEBI
(4S,5S)-5-HYDROXY-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylate	Generator
(S,S)-2-Methyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine-4-carboxylate	Generator
b-Hydroxyectoine	Generator
Β-hydroxyectoine	Generator
5-Hydroxyectoine	MeSH

Chemical Formula

C₆H₁₀N₂O₃

Average Molecular Mass

158.155 g/mol

Monoisotopic Mass

158.069 g/mol

CAS Registry Number

165542-15-4

IUPAC Name

(4S,5S)-5-hydroxy-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid

Traditional Name

5-hydroxyectoine

SMILES

[H][C@]1(O)CN=C(C)N[C@]1([H])C(O)=O

InChI Identifier

InChI=1S/C6H10N2O3/c1-3-7-2-4(9)5(8-3)6(10)11/h4-5,9H,2H2,1H3,(H,7,8)(H,10,11)/t4-,5-/m0/s1

InChI Key

KIIBBJKLKFTNQO-WHFBIAKZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Hydropyrimidine carboxylic acid derivative
Beta-hydroxy acid
Hydropyrimidine
1,4,5,6-tetrahydropyrimidine
Hydroxy acid
Imidolactam
Secondary alcohol
Amidine
Carboxylic acid amidine
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

iminium betaine (CHEBI:85413 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	17.7 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-3.2	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	2.61	ChemAxon
pKa (Strongest Basic)	9.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.14 m³·mol⁻¹	ChemAxon
Polarizability	14.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-0900000000-abd891a4570682f765b3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dl-1900000000-abe7f8ff0e73a01a76e1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9000000000-961e39aabd5018ec55f9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bt9-1900000000-d5dd239ec5b802cb7432	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-5900000000-ae9f9da2de49174e2112	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ukc-9000000000-7f02ba344ab67a14b5d7	Not Available	View Spectrum
MS	MS Spectrum	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2760.0 Log mg/kg [1600:4900]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000019	Indoor air?Indoor air can be a significant reservoir for synthetic chemical contaminants, which often originate from various sources within enclosed environments.	Air, dust & atmospheric transport	Not Available
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000609	Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.	Personal care & cosmetics	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000619	Manicure Pedicure?Manicure and pedicure procedures often involve the use of various synthetic chemicals, including solvents, nail polishes, and nail adhesives.	Personal care & cosmetics	PubChem
CEDs000630	Toys?Toys, particularly those made from synthetic materials such as plastics, can be a source of chemical contamination due to the presence of various additives and compounds used in their production.	Recreation & sports surfaces	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000730	Contact Lens Cases?Contact lens cases are small containers designed to store contact lenses in a sterile environment, typically made from various synthetic materials including plastics such as polypropylene or polycarbonate.	Healthcare, pharmaceuticals & veterinary products	PubChem
CEDs000738	Cooling Circuit Water?Cooling circuit water is utilized in various industrial processes to absorb and dissipate heat generated during operations.	Industrial manufacturing & chemical processing	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Fumarate hydratase, mitochondrial	P10173	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.357 Applicability Domain 0.357 Statistical Significance 1.00e-05 Supporting Reference Compounds 1 E-value 0.0778492
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 7	P35236	Humans	Predicted (SEA)	Prediction Confidence Score 0.258 Applicability Domain 0.28 Low confidence Statistical Significance 0.0279 Supporting Reference Compounds 130 E-value 217.277
Click to view 3D structure	Heat shock 70 kDa protein 1A	P0DMV8	Humans	Predicted (SEA)	Prediction Confidence Score 0.258 Applicability Domain 0.28 Low confidence Statistical Significance 1.30e-04 Supporting Reference Compounds 19 E-value 1.01204
Click to view 3D structure	Dual specificity protein phosphatase 6	Q64346	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.255 Applicability Domain 0.28 Low confidence Statistical Significance 0.0025 Supporting Reference Compounds 53 E-value 19.2288
Click to view 3D structure	Protein Tat	P04608	Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1)	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.28 Low confidence Statistical Significance 0.022 Supporting Reference Compounds 108 E-value 171.658
Click to view 3D structure	Nuclear receptor subfamily 4immunitygroup A member 1	P22736	Humans	Predicted (SEA)	Prediction Confidence Score 0.222 Applicability Domain 0.28 Low confidence Statistical Significance 0.0342 Supporting Reference Compounds 39 E-value 266.556
Click to view 3D structure	Glutamate receptor ionotropic, kainate 4	Q01812	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.22 Applicability Domain 0.244 Low confidence Statistical Significance 6.00e-05 Supporting Reference Compounds 2 E-value 0.467095
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	Prediction Confidence Score 0.219 Applicability Domain 0.28 Low confidence Statistical Significance 0.28 Supporting Reference Compounds 343 E-value 2179.7
Click to view 3D structure	Glutamate receptor 4	P19493	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.215 Applicability Domain 0.244 Low confidence Statistical Significance 0.0032 Supporting Reference Compounds 25 E-value 24.7561
Click to view 3D structure	Eukaryotic translation initiation factor 4E	P63073	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.213 Applicability Domain 0.28 Low confidence Statistical Significance 0.0059 Supporting Reference Compounds 23 E-value 46.0867
Click to view 3D structure	Glutamate receptor ionotropic, kainate 2	P42260	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.213 Applicability Domain 0.244 Low confidence Statistical Significance 0.0021 Supporting Reference Compounds 18 E-value 16.1926
Click to view 3D structure	Glutamate receptor ionotropic, kainate 1	P22756	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.244 Low confidence Statistical Significance 0.0221 Supporting Reference Compounds 45 E-value 172.28
Click to view 3D structure	Sodium/iodide cotransporter	Q63008	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.203 Applicability Domain 0.203 Low confidence Statistical Significance 0.0494 Supporting Reference Compounds 1 E-value 384.964
Click to view 3D structure	Glutamate receptor ionotropic, kainate 3	P42264	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.203 Applicability Domain 0.244 Low confidence Statistical Significance 0.0115 Supporting Reference Compounds 26 E-value 89.9158
Click to view 3D structure	Glutamate receptor ionotropic, kainate 5	Q61626	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.202 Applicability Domain 0.203 Low confidence Statistical Significance 6.00e-04 Supporting Reference Compounds 2 E-value 4.67095
Click to view 3D structure	Glutamate receptor 3	P19492	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.201 Applicability Domain 0.244 Low confidence Statistical Significance 0.0122 Supporting Reference Compounds 30 E-value 94.9761
Click to view 3D structure	Glutamate receptor 1	P19490	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.201 Applicability Domain 0.244 Low confidence Statistical Significance 0.0441 Supporting Reference Compounds 37 E-value 343.082
Click to view 3D structure	Glutamate receptor 2	P19491	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.201 Applicability Domain 0.244 Low confidence Statistical Significance 0.0086 Supporting Reference Compounds 34 E-value 66.8725
Click to view 3D structure	Small ubiquitin-related modifier 1	P63165	Humans	Predicted (SEA)	Prediction Confidence Score 0.2 Applicability Domain 0.28 Low confidence Statistical Significance 0.257 Supporting Reference Compounds 95 E-value 2000.8
Click to view 3D structure	SH3 and multiple ankyrin repeat domains protein 3	Q4ACU6	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.2 Applicability Domain 0.2 Low confidence Statistical Significance 6.70e-04 Supporting Reference Compounds 1 E-value 5.2159
Click to view 3D structure	DNA dC->dU-editing enzyme APOBEC-3G	Q9HC16	Humans	Predicted (SEA)	Prediction Confidence Score 0.197 Applicability Domain 0.28 Low confidence Statistical Significance 0.1601 Supporting Reference Compounds 76 E-value 1246.13
Click to view 3D structure	DNA dC->dU-editing enzyme APOBEC-3A	P31941	Humans	Predicted (SEA)	Prediction Confidence Score 0.197 Applicability Domain 0.28 Low confidence Statistical Significance 0.0756 Supporting Reference Compounds 28 E-value 588.618
Click to view 3D structure	Thymidine phosphorylase	Q5FVR2	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.196 Applicability Domain 0.196 Low confidence Statistical Significance 0.0016 Supporting Reference Compounds 1 E-value 12.1445
Click to view 3D structure	Extended-spectrum beta-lactamase PER-6	D5HSX5	Aeromonas allosaccharophila	Predicted (SEA)	Prediction Confidence Score 0.196 Applicability Domain 0.196 Low confidence Statistical Significance 5.20e-04 Supporting Reference Compounds 1 E-value 4.04816
Click to view 3D structure	ADC-14 protein	Q0VTR6	Acinetobacter genomosp. 3	Predicted (SEA)	Prediction Confidence Score 0.196 Applicability Domain 0.196 Low confidence Statistical Significance 5.20e-04 Supporting Reference Compounds 1 E-value 4.04816