Cannabis Compound Database: Showing Compound Card for SAICAR (CDB004865)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:44:45 UTC

Updated at

2020-12-07 19:11:08 UTC

CannabisDB ID

CDB004865

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

SAICAR

Description

SAICAR, also known as succino-aicar or saicaribotide, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. Many affected children with organic acidemias experience intellectual disability or delayed development. SAICAR is a strong basic compound (based on its pKa). SAICAR exists in all eukaryotes, ranging from yeast to humans. Within humans, SAICAR participates in a number of enzymatic reactions. In particular, SAICAR can be biosynthesized from 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate and L-aspartic acid through its interaction with the enzyme multifunctional protein ADE2. In addition, SAICAR can be converted into fumaric acid and AICAR; which is catalyzed by the enzyme adenylosuccinate lyase. When present in sufficiently high levels, SAICAR can act as an oncometabolite, a metabotoxin, and an acidogen. In humans, SAICAR is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. Outside of the human body, SAICAR has been detected, but not quantified in, several different foods, such as canola, sago palms, cashew nuts, giant butterburs, and swedes. This could make SAICAR a potential biomarker for the consumption of these foods. SAICAR (or (S)-2-succinate) is a substrate for the multifunctional protein ADE2. SAICAR is a potentially toxic compound. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. SAICAR, with regard to humans, has been linked to several inborn metabolic disorders including fumarase deficiency and atic deficiency. These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. As an oncometabolite, high levels of SAICAR stimulate pyruvate kinase isoform M2 and promote cancer cell survival in glucose-limited conditions such as aerobic glycolysis (PMID: 23086999 ). SAICAR is an intermediate in purine metabolism. As an organic acid, SAICAR is associated with acidosis. SAICAR 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
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acid	ChEBI
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate	ChEBI
1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole	ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole	ChEBI
5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole	ChEBI
Succino-aicar	ChEBI
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate	ChEBI
Succinylaminoimidazolecarboxamide ribose-5'-phosphate	ChEBI
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinate	Generator
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinic acid	Generator
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinate	Generator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinate	Generator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinic acid	Generator
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acid	Generator
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphoric acid	Generator
Succinylaminoimidazolecarboxamide ribose-5'-phosphoric acid	Generator
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate	HMDB
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acid	HMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate	HMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid	HMDB
(S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate	HMDB
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole	HMDB
5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole	HMDB
5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide	HMDB
L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)	HMDB
L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)	HMDB
N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate	HMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate	HMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid	HMDB
Phosphoribosylaminoimidazolesuccinocarboxamide	HMDB
N-(5-Amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate	HMDB
5'-Phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole	HMDB
SAICAR, (D)-isomer	HMDB
SAICAribotide	HMDB
Succinylaminoimidazole carboxamide ribotide	HMDB
SAICA ribotide	HMDB
Succinylaminoimidazolecarboxamide ribose-5’-phosphate	HMDB

Chemical Formula

C₁₃H₁₉N₄O₁₂P

Average Molecular Weight

454.28

Monoisotopic Molecular Weight

454.0737

IUPAC Name

(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid

Traditional Name

saicar

CAS Registry Number

3031-95-6

SMILES

NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O

InChI Identifier

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

InChI Key

NAQGHJTUZRHGAC-ZZZDFHIKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Imidazole ribonucleosides and ribonucleotides

Sub Class

1-ribosyl-imidazolecarboxamides

Direct Parent

1-ribosyl-imidazolecarboxamides

Alternative Parents

Substituents

1-ribosyl-imidazolecarboxamide
Pentose-5-phosphate
Pentose phosphate
Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Alpha-amino acid or derivatives
Pentose monosaccharide
2-heteroaryl carboxamide
Imidazolyl carboxylic acid derivative
Imidazole-4-carbonyl group
Monoalkyl phosphate
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Dicarboxylic acid or derivatives
Phosphoric acid ester
Aminoimidazole
Monosaccharide
Imidazole
Heteroaromatic compound
Azole
Vinylogous amide
Tetrahydrofuran
Amino acid or derivatives
Carboxamide group
Amino acid
1,2-diol
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-(phosphoribosyl)imidazolecarboxamide (CHEBI:18319 )

Ontology

Physiological effect

Health effect:

Health condition:

Atic deficiency

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Subcellular:

Organ and components:

Intestine

Cell and elements:

Cell:

Fibroblast

Biofluid and excreta:

Role

Biological role:

Oncometabolite

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	-1.8	ALOGPS
logP	-4.8	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	4.54	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	263.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	90.65 m³·mol⁻¹	ChemAxon
Polarizability	38.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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
Predicted GC-MS	SAICAR, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05n1-9732500000-f3a7f13b1dee5f81c7a8	Spectrum
Predicted GC-MS	SAICAR, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05ot-9600116000-74a62efcb34072bbe352	Spectrum
Predicted GC-MS	SAICAR, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	SAICAR, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-055o-1592600000-05db249dfb0f14143f9f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-3950000000-6ebf6a64483dd1392782	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001l-5940000000-e218e278f5195eb90341	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ug3-6381900000-4fec69ff813fe652ea7d	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9350000000-e4e387627fbca1ef1201	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-95f6153e96335a5d2b32	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f79-2012900000-f38ec5261c12799bc354	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9022000000-a24939a2980b6834f5bc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9110000000-7f66eadbb3c3527bbc8c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0024900000-6f3c27fcd647c50d79d0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0096-1293000000-d46017274b02e79e4277	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-3891000000-ed7da10b4a914197adb3	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Purine Metabolism
Adenosine Deaminase Deficiency		Not Available
Adenylosuccinate Lyase Deficiency		Not Available
Gout or Kelley-Seegmiller Syndrome		Not Available
Lesch-Nyhan Syndrome (LNS)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Adenylosuccinate lyase	ADSL	22q13.2	P30566	details
Multifunctional protein ADE2	PAICS	4q12	P22234	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000797

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022251

KNApSAcK ID

Not Available

Chemspider ID

141175

KEGG Compound ID

C04823

BioCyc ID

P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE

BiGG ID

44624

Wikipedia Link

Phosphoribosylaminoimidazolesuccinocarboxamide

METLIN ID

5762

PubChem Compound

160666

PDB ID

Not Available

ChEBI ID

18319

References

General References

Keller KE, Tan IS, Lee YS: SAICAR stimulates pyruvate kinase isoform M2 and promotes cancer cell survival in glucose-limited conditions. Science. 2012 Nov 23;338(6110):1069-72. doi: 10.1126/science.1224409. Epub 2012 Oct 18. [PubMed:23086999 ]

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. Multifunctional protein ADE2

General function:: Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:: Not Available
Gene Name:: PAICS
Uniprot ID:: P22234
Molecular weight:: 47078.82

Showing Compound Card for SAICAR (CDB004865)

Structure for CDB004865 (SAICAR)

Enzymes