Cannabis Compound Database: Showing Compound Card for Argininosuccinic acid (CDB005104)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4) Show 5 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:09:43 UTC

Updated at

2020-11-18 16:39:22 UTC

CannabisDB ID

CDB005104

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Argininosuccinic acid

Description

Argininosuccinic acid, also known as L-argininosuccinate or ASA, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Argininosuccinic acid is a very strong basic compound (based on its pKa). Argininosuccinic acid exists in all living species, ranging from bacteria to humans. Within humans, argininosuccinic acid participates in a number of enzymatic reactions. In particular, argininosuccinic acid can be converted into fumaric acid and L-arginine; which is catalyzed by the enzyme argininosuccinate lyase. In addition, argininosuccinic acid can be biosynthesized from citrulline and L-aspartic acid; which is mediated by the enzyme argininosuccinate synthase. Argininosuccinic acid in affected individuals is excreted by the kidney at a rate practically equivalent to the glomerular filtration rate (GFR). In humans, argininosuccinic acid is involved in the metabolic disorder called argininemia. Argininosuccinic acid is a precursor to fumarate in the citric acid cycle via Argininosuccinic acid lyase. Argininosuccinic acid is a potentially toxic compound. Argininosuccinic acid, with regard to humans, has been found to be associated with the diseases such as argininosuccinyl-coa lyase deficiency; argininosuccinic acid has also been linked to several inborn metabolic disorders including argininosuccinic aciduria and argininemia. Argininosuccinic acid (ASA) lyase deficiency results in defective cleavage of ASA. Extreme symptoms include coma and cerebral edema. Argininosuccinic 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
2-(Nomega-L-arginino)succinate	Kegg
L-Argininosuccinate	Kegg
L-Argininosuccinic acid	Kegg
L-Arginosuccinic acid	Kegg
2-(Nomega-L-arginino)succinic acid	Generator
L-Arginosuccinate	Generator
Argininosuccinate	Generator
2-(N(Omega)-L-arginine)succinate	HMDB
2-(N(Omega)-L-arginine)succinic acid	HMDB
2-(N(Omega)-L-arginino)succinate	HMDB
2-(N(Omega)-L-arginino)succinic acid	HMDB
2-(Nw-l-arginino)butanedioate	HMDB
2-(Nw-l-arginino)butanedioic acid	HMDB
Arginosuccinate	HMDB
Arginosuccinic acid	HMDB
ASA	HMDB
N(Omega)-(L-arginino)succinate	HMDB
N(Omega)-(L-arginino)succinic acid	HMDB
N-(((4-Amino-4-carboxybutyl)amino)iminomethyl)-L-aspartate	HMDB
N-(((4-Amino-4-carboxybutyl)amino)iminomethyl)-L-aspartic acid	HMDB
N-(L-Arginino) succinate	HMDB
N-(L-Arginino) succinic acid	HMDB
N-(L-Arginino)succinate	HMDB
N-(L-Arginino)succinic acid	HMDB
N-[(4-Amino-4-carboxybutyl)amidino]-L-aspartate	HMDB
N-[(4-Amino-4-carboxybutyl)amidino]-L-aspartic acid	HMDB
N-[[(4-Amino-4-carboxybutyl)amino]iminomethyl]-L-aspartate	HMDB
N-[[(4-Amino-4-carboxybutyl)amino]iminomethyl]-L-aspartic acid	HMDB
Acid, argininosuccinic	HMDB
N-(4-Amino-4-carboxybutyl)amidino-L-aspartic acid	HMDB

Chemical Formula

C₁₀H₁₈N₄O₆

Average Molecular Weight

290.27

Monoisotopic Molecular Weight

290.1226

IUPAC Name

(2S)-2-{N'-[(4S)-4-amino-4-carboxybutyl]carbamimidamido}butanedioic acid

Traditional Name

argininosuccinic acid

CAS Registry Number

2387-71-5

SMILES

N[C@@H](CCCNC(=N)N[C@@H](CC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H18N4O6/c11-5(8(17)18)2-1-3-13-10(12)14-6(9(19)20)4-7(15)16/h5-6H,1-4,11H2,(H,15,16)(H,17,18)(H,19,20)(H3,12,13,14)/t5-,6-/m0/s1

InChI Key

KDZOASGQNOPSCU-WDSKDSINSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
Alpha-amino acid
L-alpha-amino acid
Tricarboxylic acid or derivatives
Guanidine
Amino acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Organic nitrogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Other amino acids (C03406 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Biofluid and excreta:

Subcellular:

Cytoplasm

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	-3.2	ALOGPS
logP	-5.8	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.14	ChemAxon
pKa (Strongest Basic)	12.39	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	185.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	75.31 m³·mol⁻¹	ChemAxon
Polarizability	27.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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	Argininosuccinic acid, non-derivatized, GC-MS Spectrum	splash10-0007-0921100000-638b5887a29712423afd	Spectrum
Predicted GC-MS	Argininosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0007-8790000000-bc8aa39ecc71a1589298	Spectrum
Predicted GC-MS	Argininosuccinic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-4101900000-c606d87ec7ffb8ef2cfa	Spectrum
Predicted GC-MS	Argininosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Argininosuccinic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0090000000-27e7b2225bca7ed0bfef	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-0390000000-b66871354ad66743ff5f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-1910000000-777b6f2263b573f38bca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001i-3900000000-26d6466903550c40fde6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001r-8900000000-4e5455a5af85574ac9df	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0006-0090000000-79b7ca9043632dc877e1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0006-0590000000-8fb4f4625f241d387e92	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-06di-3910000000-55530a4477a3fde8c1c1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-9200000000-413c3029964c0386047a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00di-9000000000-6ffc3b2b5da5f69de80b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-060r-0950000000-129ee81e1370707d975d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a4i-0910000000-62431d9967ced6c96b28	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-1980000000-27b5f442d411115ebaab	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a4i-1900000000-b57bcbf0c07e921767af	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0006-3900000000-1fce5114c61349fc9065	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-014i-0900000000-25c094a4a18cfe463b6b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-9200000000-e518e242f12e95bbddf9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-9000000000-932dfd009a8e5c41ec38	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0090000000-27e7b2225bca7ed0bfef	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dj-0190000000-8ba86e35661de03d1049	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0092-2890000000-966d24fb4f820888318e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-4900000000-5200a801423dd1a4b7a6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00ds-0290000000-a3397e8c303fc7e6bd83	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00e9-0940000000-a964172e915808d27899	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ac3-8900000000-d4ac87f770202453bb7a	2017-09-01	View Spectrum

NMR

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

Pathways

Name	SMPDB/Pathwhiz	KEGG
Arginine and Proline Metabolism
Aspartate Metabolism
Urea Cycle
Canavan Disease		Not Available
Hypoacetylaspartia		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Adenylosuccinate lyase	ADSL	22q13.2	P30566	details
Argininosuccinate synthase	ASS1	9q34.1	P00966	details
Argininosuccinate lyase	ASL	7q11.21	P04424	details
Cholinephosphotransferase 1	CHPT1	12q	Q8WUD6	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cholinephosphotransferase 1	CHPT1	12q	Q8WUD6	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000052

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Argininosuccinic acid

METLIN ID

5115

PubChem Compound

16950

PDB ID

Not Available

ChEBI ID

15682

References

General References

Not Available

Enzymes

Enzyme Details

1. Adenylosuccinate lyase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ADSL
Uniprot ID:: P30566
Molecular weight:: 54888.735

Enzyme Details

2. Argininosuccinate synthase

General function:: Involved in argininosuccinate synthase activity
Specific function:: Not Available
Gene Name:: ASS1
Uniprot ID:: P00966
Molecular weight:: 46530.055

Enzyme Details

3. Argininosuccinate lyase

General function:: Involved in argininosuccinate lyase activity
Specific function:: Not Available
Gene Name:: ASL
Uniprot ID:: P04424
Molecular weight:: 51657.505

Enzyme Details

4. Cholinephosphotransferase 1

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Catalyzes phosphatidylcholine biosynthesis from CDP-choline. It thereby plays a central role in the formation and maintenance of vesicular membranes.
Gene Name:: CHPT1
Uniprot ID:: Q8WUD6
Molecular weight:: 45096.535

Showing Compound Card for Argininosuccinic acid (CDB005104)

Structure for CDB005104 (Argininosuccinic acid)

Enzymes