Cannabis Compound Database: Showing Compound Card for Ureidopropionic acid (CDB004784)

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Record Information

Version

1.0

Created at

2020-04-17 18:36:25 UTC

Updated at

2020-11-18 16:38:40 UTC

CannabisDB ID

CDB004784

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Ureidopropionic acid

Description

Ureidopropionic acid, also known as 3-ureidopropanoate or N-carbamoyl-b-alanine, belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group. Ureidopropionic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Ureidopropionic acid exists in all living organisms, ranging from bacteria to humans. Within humans, ureidopropionic acid participates in a number of enzymatic reactions. In particular, ureidopropionic acid can be converted into β-alanine through its interaction with the enzyme Beta-ureidopropionase. In addition, ureidopropionic acid can be biosynthesized from dihydrouracil through its interaction with the enzyme dihydropyrimidinase. In humans, ureidopropionic acid is involved in beta-alanine metabolism. A beta-alanine derivative that is propionic acid bearing a ureido group at position 3. Outside of the human body, Ureidopropionic acid has been detected, but not quantified in, several different foods, such as gram beans, broccoli, climbing beans, oriental wheats, and mandarin orange (clementine, tangerine). This could make ureidopropionic acid a potential biomarker for the consumption of these foods. Ureidopropionic acid is a potentially toxic compound. Ureidopropionic 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-[(Aminocarbonyl)amino]propanoic acid	ChEBI
3-Ureidopropanoate	ChEBI
3-Ureidopropanoic acid	ChEBI
3-Ureidopropionate	ChEBI
3-Ureidopropionic acid	ChEBI
beta-Ureidopropionic acid	ChEBI
N-(AMINOCARBONYL)-BETA-alanine	ChEBI
Ureidopropanoic acid	ChEBI
N-Carbamoyl-beta-alanine	Kegg
3-[(Aminocarbonyl)amino]propanoate	Generator
b-Ureidopropionate	Generator
b-Ureidopropionic acid	Generator
beta-Ureidopropionate	Generator
Β-ureidopropionate	Generator
Β-ureidopropionic acid	Generator
N-(AMINOCARBONYL)-b-alanine	Generator
N-(AMINOCARBONYL)-β-alanine	Generator
Ureidopropanoate	Generator
N-Carbamoyl-b-alanine	Generator
N-Carbamoyl-β-alanine	Generator
Ureidopropionate	Generator
3-(carbamoylamino)Propanoate	HMDB
3-(carbamoylamino)Propanoic acid	HMDB
3-ureido-Propionate	HMDB
Carbamoyl-b-ala-OH	HMDB
Carbamoyl-beta-ala-OH	HMDB
N-(Aminocarbonyl)-'b-alanine	HMDB
N-Carbamyl-b-alanine	HMDB
N-Carbamyl-beta-alanine	HMDB
Ion(-1) OF N-carbamoyl-beta-alanine	MeSH, HMDB
Carbamoyl-beta-alanine	HMDB
Carbamoyl-β-alanine	HMDB
Carbamyl beta-alanine	HMDB
Carbamyl β-alanine	HMDB
beta-Ureidopropanoic acid	HMDB
β-Ureidopropanoic acid	HMDB

Chemical Formula

C₄H₈N₂O₃

Average Molecular Weight

132.12

Monoisotopic Molecular Weight

132.0535

IUPAC Name

3-(carbamoylamino)propanoic acid

Traditional Name

ureidopropionic acid

CAS Registry Number

462-88-4

SMILES

NC(=O)NCCC(O)=O

InChI Identifier

InChI=1S/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)

InChI Key

JSJWCHRYRHKBBW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic carbonic acids and derivatives

Sub Class

Ureas

Direct Parent

Ureas

Alternative Parents

Substituents

Urea
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

beta-alanine derivative (CHEBI:18261 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Subcellular:

Cytoplasm

Role

Biological role:

Metabolite

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	20.9 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.98	ALOGPS
logP	-1.4	ChemAxon
logS	-0.4	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.82 m³·mol⁻¹	ChemAxon
Polarizability	12.07 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
GC-MS	Ureidopropionic acid, non-derivatized, GC-MS Spectrum	splash10-002f-3910000000-bbd51b3bb30ff8d230d3	Spectrum
GC-MS	Ureidopropionic acid, 1 TMS, GC-MS Spectrum	splash10-00n0-5900000000-00dc280a63401c96ec2a	Spectrum
GC-MS	Ureidopropionic acid, 3 TMS, GC-MS Spectrum	splash10-0udi-2930000000-fcdce5cf4a20023c403a	Spectrum
GC-MS	Ureidopropionic acid, 2 TMS, GC-MS Spectrum	splash10-0hr0-2900000000-8a898fc59206b3f30a13	Spectrum
GC-MS	Ureidopropionic acid, non-derivatized, GC-MS Spectrum	splash10-002f-3910000000-bbd51b3bb30ff8d230d3	Spectrum
GC-MS	Ureidopropionic acid, non-derivatized, GC-MS Spectrum	splash10-00n0-5900000000-00dc280a63401c96ec2a	Spectrum
GC-MS	Ureidopropionic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-2930000000-fcdce5cf4a20023c403a	Spectrum
GC-MS	Ureidopropionic acid, non-derivatized, GC-MS Spectrum	splash10-0hr0-2900000000-8a898fc59206b3f30a13	Spectrum
GC-MS	Ureidopropionic acid, non-derivatized, GC-MS Spectrum	splash10-0udj-1910000000-83ab1eb4328f8caae993	Spectrum
GC-MS	Ureidopropionic acid, non-derivatized, GC-MS Spectrum	splash10-0v01-0900000000-aeacd84d8e0e91418232	Spectrum
Predicted GC-MS	Ureidopropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-9000000000-f7cdf5fc49adf0b5e726	Spectrum
Predicted GC-MS	Ureidopropionic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dr-9300000000-7b12845cd5bc4d02874c	Spectrum
Predicted GC-MS	Ureidopropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ureidopropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ureidopropionic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ureidopropionic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ureidopropionic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ureidopropionic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Ureidopropionic acid, TBDMS_1_3, 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, Positive (Annotated)	splash10-00r6-9500000000-7ea8c95e3dc6296a07e9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9100000000-7b61b087fbf6c821bdd0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0596-9200000000-79dfb7a1a6838745e178	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-014l-8900000000-9bfe2297b9071d10d7e5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-001i-2900000000-e1e9196162c1cd0606e6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-001r-5900000000-0e75c38978d4fd27ad1b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-001r-8900000000-d71c6b65e5ea4a2b98a2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-0019-9600000000-995ba80b11e5e2fdbed6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-9300000000-efa2833fbedc0d3bd746	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-9200000000-92bf1d8bc142b2e065f4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-9100000000-e52a09e58825a4f43bbb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-000i-9000000000-0a7fa362cd3cbcf81534	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-9000000000-88ef7f8836542c76d47b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-000i-9000000000-223a7c6bd0e90d91dacf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-000i-9000000000-eefd307fa9aedb8dbaaa	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-000i-9000000000-ae89b554e34311f8358b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-000i-9000000000-1cfc112d7baf56aa65ab	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, negative	splash10-000i-9100000000-97d06beb4575ef6147d7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, negative	splash10-0a4i-9000000000-08bac9ac1941233e516c	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-7900000000-684d9877d084bfc7c955	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9100000000-0b6f9ea311703e9ecf13	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00b9-9000000000-1cb23a8265b882313309	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001c-9300000000-2cec50bd5b226a288c82	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9100000000-63ecd2f9ef02c677503d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-396bc860a5f8f06ff7c5	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Beta-Alanine Metabolism
Pyrimidine Metabolism
GABA-Transaminase Deficiency		Not Available
Ureidopropionase Deficiency		Not Available
Carnosinuria, carnosinemia		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Dihydropyrimidinase	DPYS	8q22	Q14117	details
Beta-ureidopropionase	UPB1	22q11.2	Q9UBR1	details
Dihydropyrimidinase-related protein 3	DPYSL3	5q32	Q14195	details
Dihydropyrimidinase-related protein 2	DPYSL2	8p22-p21	Q16555	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Dihydropyrimidinase	DPYS	8q22	Q14117	details
Beta-ureidopropionase	UPB1	22q11.2	Q9UBR1	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0062812

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021879

KNApSAcK ID

Not Available

Chemspider ID

109

KEGG Compound ID

C02642

BioCyc ID

3-UREIDO-PROPIONATE

BiGG ID

Not Available

Wikipedia Link

3-Ureidopropionic_acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18261

References

General References

Not Available

Enzymes

Enzyme Details

1. Dihydropyrimidinase

General function:: Involved in hydrolase activity
Specific function:: Catalyzes the second step of the reductive pyrimidine degradation, the reversible hydrolytic ring opening of dihydropyrimidines. Can catalyze the ring opening of 5,6-dihydrouracil to N-carbamyl-alanine and of 5,6-dihydrothymine to N-carbamyl-amino isobutyrate.
Gene Name:: DPYS
Uniprot ID:: Q14117
Molecular weight:: 56629.36

Enzyme Details

2. Beta-ureidopropionase

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
Specific function:: Converts N-carbamyl-beta-aminoisobutyric acid and N-carbamyl-beta-alanine to, respectively, beta-aminoisobutyric acid and beta-alanine, ammonia and carbon dioxide.
Gene Name:: UPB1
Uniprot ID:: Q9UBR1
Molecular weight:: 43165.705

Enzyme Details

3. Dihydropyrimidinase-related protein 3

General function:: Involved in hydrolase activity
Specific function:: Necessary for signaling by class 3 semaphorins and subsequent remodeling of the cytoskeleton. Plays a role in axon guidance, neuronal growth cone collapse and cell migration
Gene Name:: DPYSL3
Uniprot ID:: Q14195
Molecular weight:: 61962.8

Enzyme Details

4. Dihydropyrimidinase-related protein 2

General function:: Nucleotide transport and metabolism
Specific function:: Necessary for signaling by class 3 semaphorins and subsequent remodeling of the cytoskeleton. Plays a role in axon guidance, neuronal growth cone collapse and cell migration
Gene Name:: DPYSL2
Uniprot ID:: Q16555
Molecular weight:: 62293.1

Showing Compound Card for Ureidopropionic acid (CDB004784)

Structure for CDB004784 (Ureidopropionic acid)

Enzymes