Cannabis Compound Database: Showing Compound Card for 4-Hydroxybutyric acid (CDB005112)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4)transporters (4) Show 10 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:10:30 UTC

Updated at

2020-12-07 19:11:36 UTC

CannabisDB ID

CDB005112

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

4-Hydroxybutyric acid

Description

4-Hydroxybutyric acid, also known as 4-hydroxybutanoate or gamma hydroxybutyrate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 4-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Hydroxybutyric acid is a potentially toxic compound. 4-Hydroxybutyric 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
3-Carboxypropoxy acid	ChEBI
4-Hydroxy-butyric acid	ChEBI
4-Hydroxyalkanoic acid	ChEBI
4-Hydroxybutanoate	ChEBI
4-Hydroxybutanoic acid	ChEBI
4-Hydroxycarboxylic acid	ChEBI
Gamma Hydroxybutyric acid	ChEBI
gamma-Hydroxybutyric acid	ChEBI
GHB	ChEBI
Oxy-N-butyric acid	ChEBI
Xyrem	ChEBI
4-Hydroxy-butyrate	Generator
4-Hydroxyalkanoate	Generator
4-Hydroxycarboxylate	Generator
g Hydroxybutyrate	Generator
g Hydroxybutyric acid	Generator
gamma Hydroxybutyrate	Generator
Γ hydroxybutyrate	Generator
Γ hydroxybutyric acid	Generator
g-Hydroxybutyrate	Generator
g-Hydroxybutyric acid	Generator
gamma-Hydroxybutyrate	Generator
Γ-hydroxybutyrate	Generator
Γ-hydroxybutyric acid	Generator
Oxy-N-butyrate	Generator
4-Hydroxybutyrate	Generator
4-Hydroxy-butanoate	HMDB
4-Hydroxy-butanoic acid	HMDB
4-Hydroxybutyrate sodium	HMDB
4-Hydroxybutyric acid monosodium salt	HMDB
gamma-Hydroxy butyrate	HMDB
gamma-Hydroxy sodium butyrate	HMDB
gamma-Hydroxybutyrate sodium	HMDB
Hydroxybutyric acid	HMDB

Chemical Formula

C₄H₈O₃

Average Molecular Weight

104.1

Monoisotopic Molecular Weight

104.0473

IUPAC Name

4-hydroxybutanoic acid

Traditional Name

gamma hydroxybutyric acid

CAS Registry Number

591-81-1

SMILES

OCCCC(O)=O

InChI Identifier

InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)

InChI Key

SJZRECIVHVDYJC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Short-chain hydroxy acid
Hydroxy fatty acid
Straight chain fatty 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

4-hydroxy monocarboxylic acid (CHEBI:30830 )
hydroxybutyric acid (CHEBI:30830 )
Hydroxy fatty acids (LMFA01050006 )

Ontology

Aciduria

Metabolism and nutrition disorders:

Glutaric aciduria type 2

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Tissue and substructures:

Placenta

Subcellular:

Biofluid and excreta:

Source:

Biological:

Animal

Microbe:

Pseudomonas:

Pseudomonas putida

Aeromonas:

Aeromonas hydrophila

Escherichia:

Escherichia coli

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Sedative

Indirect biological role:

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	-0.63	ALOGPS
logP	-0.51	ChemAxon
logS	0.68	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-2.4	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	23.8 m³·mol⁻¹	ChemAxon
Polarizability	10.17 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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-d55d971a361b41564681	2014-09-20	View Spectrum
GC-MS	4-Hydroxybutyric acid, 2 TMS, GC-MS Spectrum	splash10-0159-2920000000-131f94186a93d0aa315d	Spectrum
GC-MS	4-Hydroxybutyric acid, non-derivatized, GC-MS Spectrum	splash10-0159-2920000000-131f94186a93d0aa315d	Spectrum
GC-MS	4-Hydroxybutyric acid, non-derivatized, GC-MS Spectrum	splash10-0002-0910000000-7240955b6b16291cf793	Spectrum
Predicted GC-MS	4-Hydroxybutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a5c-9000000000-915d32c0dbd6e6d19a55	Spectrum
Predicted GC-MS	4-Hydroxybutyric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9610000000-52e5254f6eba257ad184	Spectrum
Predicted GC-MS	4-Hydroxybutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybutyric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybutyric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybutyric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybutyric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxybutyric 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 - QqQ 10V, positive	splash10-14ii-9400000000-77378d9d837f1823ed37	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-0udi-0900000000-ca02549abb7c7402b481	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-0900000000-942af3cd327a2dd39887	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-1900000000-671c45f3bda2eabba3c1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-1900000000-36fabc35679210a4621a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-2900000000-146b4ca6698f6c40d476	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-4900000000-32e86ae76401d830a8a1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-8900000000-07fc17585cf5e8d2ba9b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0pbi-9400000000-70777a3c6521e72b59b4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0a4i-9000000000-cad0cc415c906a783cfc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0zg0-9500000000-9dfcd62aeff3ff1e731d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0pb9-9300000000-0e1b3056ef85c0fbe59d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0a4i-9200000000-144d4f05dfc0b2dbd827	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0a4i-9100000000-5a807248d180fcc738ee	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9000000000-aeb70e18a8467ef1b4b1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9000000000-50691ede3dffed6a4afb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0a4i-9000000000-13adfaf490932a7c0fb9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-000i-9000000000-3051dc4fe82b4abf5478	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0002-0900000000-8f691ae372d6f1d18226	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9100000000-80636ab7e3cb47d4d58f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n4-9000000000-71899633e269029ab7f9	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-910235f5bc92bcca7469	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-8900000000-5890f0a527dd16d9ac75	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0k9i-9200000000-241210fedf9304168090	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-21d09118dfcfcb093f8d	2015-09-15	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Sulfotransferase family cytosolic 2B member 1	SULT2B1	19q13.3	O00204	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
Aflatoxin B1 aldehyde reductase member 2	AKR7A2	1p36.13	O43488	details
Hydroxyacid-oxoacid transhydrogenase, mitochondrial	ADHFE1	8q13.1	Q8IWW8	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Monocarboxylate transporter 4	SLC16A3	17q25	O15427	details
Monocarboxylate transporter 1	SLC16A1	1p12	P53985	details
Monocarboxylate transporter 2	SLC16A7	12q13	O60669	details
Gamma-aminobutyric acid receptor subunit beta-1	GABRB1	4p12	P18505	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Hydroxyacid-oxoacid transhydrogenase, mitochondrial	ADHFE1	8q13.1	Q8IWW8	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Gamma-aminobutyric acid receptor subunit beta-1	GABRB1	4p12	P18505	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000710

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022196

KNApSAcK ID

Not Available

Chemspider ID

9984

KEGG Compound ID

C01991

BioCyc ID

4-HYDROXY-BUTYRATE

BiGG ID

Not Available

Wikipedia Link

Oxybate

METLIN ID

5678

PubChem Compound

10413

PDB ID

Not Available

ChEBI ID

30830

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. 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

3. Aflatoxin B1 aldehyde reductase member 2

General function:: Energy production and conversion
Specific function:: Catalyzes the NADPH-dependent reduction of succinic semialdehyde to gamma-hydroxybutyrate. May have an important role in producing the neuromodulator gamma-hydroxybutyrate (GHB). Has broad substrate specificity. Has NADPH-dependent aldehyde reductase activity towards 2-carboxybenzaldehyde, 2-nitrobenzaldehyde and pyridine-2-aldehyde (in vitro). Can reduce 1,2-naphthoquinone and 9,10-phenanthrenequinone (in vitro). Can reduce the dialdehyde protein-binding form of aflatoxin B1 (AFB1) to the non-binding AFB1 dialcohol. May be involved in protection of liver against the toxic and carcinogenic effects of AFB1, a potent hepatocarcinogen.
Gene Name:: AKR7A2
Uniprot ID:: O43488
Molecular weight:: 39588.65

Enzyme Details

4. Hydroxyacid-oxoacid transhydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). D,L-3-hydroxyisobutyrate and L-3-hydroxybutyrate (L-3-OHB) are also substrates for HOT with 10-fold lower activities.
Gene Name:: ADHFE1
Uniprot ID:: Q8IWW8
Molecular weight:: 50307.42

Transporters

Enzyme Details

1. Monocarboxylate transporter 4

General function:: Involved in transmembrane transport
Specific function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:: SLC16A3
Uniprot ID:: O15427
Molecular weight:: 49468.9

Enzyme Details

2. Monocarboxylate transporter 1

General function:: Involved in transmembrane transport
Specific function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:: SLC16A1
Uniprot ID:: P53985
Molecular weight:: 53957.7

Enzyme Details

3. Monocarboxylate transporter 2

General function:: Involved in transmembrane transport
Specific function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. MCT2 is a high affinity pyruvate transporter
Gene Name:: SLC16A7
Uniprot ID:: O60669
Molecular weight:: 52185.7

Enzyme Details

4. Gamma-aminobutyric acid receptor subunit beta-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRB1
Uniprot ID:: P18505
Molecular weight:: 54234.1

Showing Compound Card for 4-Hydroxybutyric acid (CDB005112)

Structure for CDB005112 (4-Hydroxybutyric acid)

Enzymes

Transporters