SAICAR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H19N4O12P
Molecular Weight	454.2833
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=C(N=CN1[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N[C@@H](CC(O)=O)C(O)=O

InChI

InChIKey=NAQGHJTUZRHGAC-ZZZDFHIKSA-N

InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C13H19N4O12P
Molecular Weight	454.2833
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Novel proton MR spectroscopy findings in adenylosuccinate lyase deficiency.	2013-04	23055421
SAICAR stimulates pyruvate kinase isoform M2 and promotes cancer cell survival in glucose-limited conditions.	2012-11-23	23086999
Oligodendroglia from ADSL-deficient patient produce SAICAribotide and SAMP.	2010-05-26	20674424
Clinical, biochemical, neuropathological and molecular findings of the first Polish case of adenylosuccinase deficiency.	2008	18368630
Adenylosuccinate lyase deficiency: the first identified polish patient.	2007-10	17485188
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.	2005	15902552
Adenylosuccinate lyase deficiency--first British case.	2004-10	15571235
Screening for adenylosuccinate lyase deficiency: clinical, biochemical and molecular findings in four patients.	2002-08	12368987
Clinical, biochemical and molecular genetic correlations in adenylosuccinate lyase deficiency.	2000-09-01	10958654
Human adenylosuccinate lyase (ADSL), cloning and characterization of full-length cDNA and its isoform, gene structure and molecular basis for ADSL deficiency in six patients.	2000-06-12	10888601
1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism.	1999-04	10102915
Detection of 5'-phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole in urine by use of the Bratton-Marshall reaction: identification of patients deficient in adenylosuccinate lyase activity.	1986-07	3740420
An infantile autistic syndrome characterised by the presence of succinylpurines in body fluids.	1984-11-10	6150139
Purines, pyrimidines, and imidazoles. Part 50. Inhibition of adenylosuccinate AMP-lyase No. 4.3.2.2. by derivatives of N-(5-amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate (SAICAR) and virazole 5'-phosphate.	1979	573277

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:25:03 GMT 2025` Edited by `admin` on `Mon Mar 31 22:25:03 GMT 2025`
Record UNII	K1PVR64RIF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SAICAR [MI]

Preferred Name

English

SAICAR

Common Name

English

L-ASPARTIC ACID, N-((5-AMINO-1-(5-O-PHOSPHONO-.BETA.-D-RIBOFURANOSYL)-1H-IMIDAZOL-4-YL)CARBONYL)-

Systematic Name

English

SUCCINO-AICAR

Common Name

English

Code System Code Type Description

PUBCHEM

160666