ContaminantDB: Succinyladenosine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:13:18 UTC

Update Date

2026-04-06 13:22:15 UTC

Accession Number

CHEM003240

Identification

Common Name

Succinyladenosine

Class

Small Molecule

Description

Succinyladenosine (SAdo) is one of the dephosphorylated enzyme substrate that accumulates in body fluids of patients with adenylosuccinate lyase (ADSL) deficiency, the other being 5-amino-4-imidazole-N-succinocarboxamide riboside (SAICAr). ADSL is an inherited metabolic disease characterized by various degrees of psychomotor retardation. The severity of the clinical presentation correlates with a low S-Ado/SAICAr ratio in body fluids. Normally Succinyladenosine is not found in blood or CSF but may be detected in trace amounts in urine. (OMIM 103050). (1, 2).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Ether
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(S)-N-(1,2-Dicarboxyethyl)-adenosine	ChEBI
6-(1,2-Dicarboxyethylamino)-9-beta-D-ribofuranosylpurine	ChEBI
N-(9-beta-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acid	ChEBI
N-9-Ribofuranosyl-9H-purin-6-yl-aspartic acid	ChEBI
Succinoadenosine	ChEBI
6-(1,2-Dicarboxyethylamino)-9-b-D-ribofuranosylpurine	Generator
6-(1,2-Dicarboxyethylamino)-9-β-D-ribofuranosylpurine	Generator
N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartate	Generator
N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acid	Generator
N-(9-beta-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartate	Generator
N-(9-Β-D-ribofuranosyl-9H-purin-6-yl)-L-aspartate	Generator
N-(9-Β-D-ribofuranosyl-9H-purin-6-yl)-L-aspartic acid	Generator
N-9-Ribofuranosyl-9H-purin-6-yl-aspartate	Generator
6-(1,2-Dicarboxyethylamino)-9-beta-delta-ribofuranosylpurine	HMDB
N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-aspartate	HMDB
N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acid	HMDB

Chemical Formula

C₁₄H₁₇N₅O₈

Average Molecular Mass

383.314 g/mol

Monoisotopic Mass

383.108 g/mol

CAS Registry Number

4542-23-8

IUPAC Name

Not Available

Traditional Name

atp - adenosine triphosphate

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N[C@@H](CC(O)=O)C(O)=O)N=CN=C12

InChI Identifier

InChI=1S/C14H17N5O8/c20-2-6-9(23)10(24)13(27-6)19-4-17-8-11(15-3-16-12(8)19)18-5(14(25)26)1-7(21)22/h3-6,9-10,13,20,23-24H,1-2H2,(H,21,22)(H,25,26)(H,15,16,18)/t5-,6+,9+,10+,13+/m0/s1

InChI Key

VKGZCEJTCKHMRL-VWJPMABRSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Aspartic acid or derivatives
Glycosyl compound
N-glycosyl compound
6-alkylaminopurine
6-aminopurine
Alpha-amino acid or derivatives
Pentose monosaccharide
L-alpha-amino acid
Imidazopyrimidine
Purine
Aminopyrimidine
Secondary aliphatic/aromatic amine
N-substituted imidazole
Monosaccharide
Pyrimidine
Dicarboxylic acid or derivatives
Imidolactam
Heteroaromatic compound
Imidazole
Tetrahydrofuran
Azole
Amino acid or derivatives
Secondary alcohol
Amino acid
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxide
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosines (CHEBI:71169 )
L-aspartic acid derivative (CHEBI:71169 )
amino dicarboxylic acid (CHEBI:71169 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Adenylosuccinate Lyase Deficiency	SMP00167	Not Available

Applications

Not Available

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	233 - 238°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.62 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-3.9	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	4.58	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.15 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	85.3 m³·mol⁻¹	ChemAxon
Polarizability	34.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0l6r-8129000000-a61f85c8b0714ae949d3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0ac0-9610066000-c7055bad2597f21774ee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0096000000-9b81fa7e1337be93a9f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-0291000000-44075e8e93da0ec9d2f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-1490000000-a88e52cec6ba27380289	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f89-0179000000-ce2528c4b8d13111f498	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0191000000-17fff23d0573f012bc9d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zgi-1290000000-dc5ba463b978c4180aab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0029000000-a86f22f01d7c9a417187	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0197000000-9173ddda3c1193d49021	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-0950000000-ec04fb75a306974e5dd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03e9-0019000000-9f98332b939a6b04fe16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kai-2169000000-a669a9e825855e307f25	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-3790000000-751176ffe8aead5db910	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000912

FooDB ID

FDB022314

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5867

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

17216022

ChEBI ID

71169

PubChem Compound ID

20849086

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Buck, Ildiko; Reese, Colin B. An unambiguous synthesis of adenylosuccinic acid and its constituent nucleoside. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1990), (11), 2937-42.

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225

2. Buck, Ildiko; Reese, Colin B. An unambiguous synthesis of adenylosuccinic acid and its constituent nucleoside. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1990), (11), 2937-42.

3. Marinaki AM, Champion M, Kurian MA, Simmonds HA, Marie S, Vincent MF, van den Berghe G, Duley JA, Fairbanks LD: Adenylosuccinate lyase deficiency--first British case. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1231-3.

4. Tsuchiya H, Hayashi T, Tatsumi M, Hoshino Y, Ohtani S, Takagi N: High-performance liquid-chromatographic analysis for serotonin and tryptamine excreted in urine after oral loading with L-tryptophan. Clin Chem. 1989 Jan;35(1):43-7.

5. Zikanova M, Krijt J, Hartmannova H, Kmoch S: Preparation of 5-amino-4-imidazole-N-succinocarboxamide ribotide, 5-amino-4-imidazole-N-succinocarboxamide riboside and succinyladenosine, compounds usable in diagnosis and research of adenylosuccinate lyase deficiency. J Inherit Metab Dis. 2005;28(4):493-9.

6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.

Succinyladenosine (CHEM003240)

Structure for CHEM003240: Succinyladenosine