Cannabis Compound Database: Showing Compound Card for (S)-3-Hydroxyisobutyric acid (CDB005157)

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Record Information

Version

1.0

Created at

2020-04-17 19:15:05 UTC

Updated at

2020-11-18 16:39:27 UTC

CannabisDB ID

CDB005157

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

(S)-3-Hydroxyisobutyric acid

Description

(S)-3-Hydroxyisobutyric acid, also known as (S)-3-hydroxy-2-methylpropanoate or 3-hydroxy-isobutyrate, 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 (S)-3-Hydroxyisobutyric acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (S)-3-Hydroxyisobutyric acid exists in all living species, ranging from bacteria to humans. The severity of this disease varies from case to case (S)-3-hydroxyisobutyric acid can be converted into (S)-methylmalonic acid semialdehyde through its interaction with the enzymes 3-hydroxyisobutyrate dehydrogenase, mitochondrial and enoyl-CoA hydratase, mitochondrial. In humans, (S)-3-hydroxyisobutyric acid is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway (S)-3-Hydroxyisobutyric acid is an intermediate in the metabolic pathways of L-valine and L-thymine amino acids. The deficient enzyme in 3HiB-uria remains unclear (S)-3-Hydroxyisobutyric acid is a potentially toxic compound (S)-3-Hydroxyisobutyric acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, colorectal cancer, and diabetes mellitus type 2; (S)-3-hydroxyisobutyric acid has also been linked to the inborn metabolic disorder 3-hydroxyisobutyric aciduria. Patients with 3-hydroxyisobutyric aciduria excrete a significant amount of (S)-3-Hydroxyisobutyric acid not only during the acute stage but also when stable. (S)-3-Hydroxyisobutyric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-3-Hydroxy-2-methylpropanoic acid	ChEBI
(S)-3-Hydroxy-2-methylpropionic acid	ChEBI
(S)-3-Hydroxy-2-methylpropanoate	Generator
(S)-3-Hydroxy-2-methylpropionate	Generator
(S)-3-Hydroxyisobutyrate	Generator
2-Methyl-L-(+)-hydracrylate	HMDB
2-Methyl-L-(+)-hydracrylic acid	HMDB
3-Hydroxy(iso)butyric acid	HMDB
3-Hydroxy-2-methyl-(S)-propanoate	HMDB
3-Hydroxy-2-methyl-(S)-propanoic acid	HMDB
3-Hydroxy-2-methylpropanoate	HMDB
3-Hydroxy-2-methylpropanoic acid	HMDB
3-Hydroxy-isobutyrate	HMDB
3-Hydroxyisobutyrate	HMDB
3-Hydroxyisobutyric acid	HMDB
(2S)-3-Hydroxy-2-methylpropanoic acid	HMDB
(2S)-3-Hydroxy-2-methylpropionic acid	HMDB
(S)-beta-Hydroxyisobutyric acid	HMDB
(S)-Β-hydroxyisobutyric acid	HMDB
(±)-3-hydroxy-2-methylpropanoic acid	HMDB
(±)-3-hydroxy-2-methylpropionic acid	HMDB
2-(Hydroxymethyl)propanoic acid	HMDB
2-(Hydroxymethyl)propionic acid	HMDB
2-Methyl-3-hydroxypropanoic acid	HMDB
2-Methyl-3-hydroxypropionic acid	HMDB
3-HIBA	HMDB
3-Hydroxy-2-methylpropionic acid	HMDB
DL-3-Hydroxyisobutyric acid	HMDB
L-(+)-beta-Hydroxyisobutyric acid	HMDB
L-(+)-Β-hydroxyisobutyric acid	HMDB
beta-Hydroxyisobutyric acid	HMDB
Β-hydroxyisobutyric acid	HMDB
3-Hydroxy-2-isobutyrate	HMDB
3-Hydroxy-2-isobutyric acid	HMDB
(S)-3-Hydroxyisobutyric acid	HMDB

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.1

Monoisotopic Molecular Weight

104.0473

IUPAC Name

(2S)-3-hydroxy-2-methylpropanoic acid

Traditional Name

(S)-3-hydroxyisobutyric acid

CAS Registry Number

2068-83-9

SMILES

C[C@@H](CO)C(O)=O

InChI Identifier

InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1

InChI Key

DBXBTMSZEOQQDU-VKHMYHEASA-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
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-hydroxyisobutyric acid (CHEBI:37373 )

Ontology

Physiological effect

Health effect:

Health condition:

Diabetes mellitus type 2

Disposition

Source:

Endogenous

Biological location:

Biofluid and excreta:

Subcellular:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.47	ALOGPS
logP	-0.26	ChemAxon
logS	0.74	ALOGPS
pKa (Strongest Acidic)	4.37	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	2	ChemAxon
Refractivity	23.62 m³·mol⁻¹	ChemAxon
Polarizability	9.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9000000000-dd1c22f7a337d3289497	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00gr-9720000000-2a61310303ff8f2a7b42	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-3-Hydroxyisobutyric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-8900000000-b51c12e744025b833f31	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-9100000000-0d72fcffff267d7bc980	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-9500000000-543c65dad21c233fc8a8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052o-9000000000-7b7dcb34e28cb55ddafb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-27deee4c6a386a43ebc3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-a7aa709e1985355b4bd9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pi0-9200000000-01a40fbe4d19283ef080	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-622de763b5ea31ff4ee6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ap3-9000000000-6c76b805d02ad21ab06a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aou-9000000000-fc5e7dbe1e224cc87d4f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-021ab3207a43699617f4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uki-9700000000-04713faa703ce789efb3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9100000000-b0202d15bd6411bc7d80	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-d2c32880fd340aac0bad	2021-09-25	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Valine, Leucine and Isoleucine Degradation
Beta-Ketothiolase Deficiency		Not Available
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency		Not Available
Propionic Acidemia		Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Sulfotransferase family cytosolic 2B member 1	SULT2B1	19q13.3	O00204	details
Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial	HADH	4q22-q26	Q16836	details
3-hydroxyisobutyrate dehydrogenase, mitochondrial	HIBADH	7p15.2	P31937	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	HIBCH	2q32.2	Q6NVY1	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000023

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021877

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

483

PubChem Compound

440873

PDB ID

Not Available

ChEBI ID

37373

References

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

Enzyme Details

2. Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name:: HADH
Uniprot ID:: Q16836
Molecular weight:: 36035.11

Enzyme Details

3. 3-hydroxyisobutyrate dehydrogenase, mitochondrial

General function:: Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:: Not Available
Gene Name:: HIBADH
Uniprot ID:: P31937
Molecular weight:: 35328.515

Enzyme Details

4. 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

Enzyme Details

5. 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA.
Gene Name:: HIBCH
Uniprot ID:: Q6NVY1
Molecular weight:: 43481.935

Showing Compound Card for (S)-3-Hydroxyisobutyric acid (CDB005157)

Structure for CDB005157 ((S)-3-Hydroxyisobutyric acid)

Enzymes