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Details

Stereochemistry ACHIRAL
Molecular Formula C4H6N4O
Molecular Weight 126.1166
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-AMINO-5-IMIDAZOLE CARBOXAMIDE

SMILES

NC(=O)C1=C(N)N=CN1

InChI

InChIKey=DVNYTAVYBRSTGK-UHFFFAOYSA-N
InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)

HIDE SMILES / InChI

Molecular Formula C4H6N4O
Molecular Weight 126.1166
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Human 5-aminoimidazole-4-carboxamide ribonucleotide transformylase/inosine 5'-monophosphate cyclohydrolase. A bifunctional protein requiring dimerization for transformylase activity but not for cyclohydrolase activity.
2001 Mar 16
Regulation of phosphatidylcholine and phosphatidylethanolamine synthesis in rat hepatocytes by 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR).
2002 Feb 15
Effect of fiber type and nutritional state on AICAR- and contraction-stimulated glucose transport in rat muscle.
2002 Jun
Effect of AICAR treatment on glycogen metabolism in skeletal muscle.
2002 Mar
Regulation of GLUT4 biogenesis in muscle: evidence for involvement of AMPK and Ca(2+).
2002 May
Mapping of the bovine genes of the de novo AMP synthesis pathway.
2004 Dec
Ca2+ and AMPK both mediate stimulation of glucose transport by muscle contractions.
2004 Feb
Preliminary study on pharmacokinetics of dacarbazine and fotemustine in glioblastoma multiforme patients does not indicate gender-specific differences.
2004 Jun
Over-expression of sterol-regulatory-element-binding protein-1c (SREBP1c) in rat pancreatic islets induces lipogenesis and decreases glucose-stimulated insulin release: modulation by 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR).
2004 Mar 15
Adenosine induces apoptosis in the human gastric cancer cells via an intrinsic pathway relevant to activation of AMP-activated protein kinase.
2004 May 15
A glucose response element from the S. cerevisiae hexose transporter HXT1 gene is sensitive to glucose in human fibroblasts.
2004 May 7
AMP-activated protein kinase and type 2 diabetes.
2006
Thrombin activates AMP-activated protein kinase in endothelial cells via a pathway involving Ca2+/calmodulin-dependent protein kinase kinase beta.
2006 Aug
Activation of the AMP-activated kinase by antidiabetes drug metformin stimulates nitric oxide synthesis in vivo by promoting the association of heat shock protein 90 and endothelial nitric oxide synthase.
2006 Feb
AMPK activation increases fatty acid oxidation in skeletal muscle by activating PPARalpha and PGC-1.
2006 Feb 3
Activation of AMP-activated protein kinase reduces hyperglycemia-induced mitochondrial reactive oxygen species production and promotes mitochondrial biogenesis in human umbilical vein endothelial cells.
2006 Jan
AMPK-mediated AS160 phosphorylation in skeletal muscle is dependent on AMPK catalytic and regulatory subunits.
2006 Jul
α2 isoform-specific activation of 5'adenosine monophosphate-activated protein kinase by 5-aminoimidazole-4-carboxamide-1-β-D-ribonucleoside at a physiological level activates glucose transport and increases glucose transporter 4 in mouse skeletal muscle.
2006 Mar
Pharmacogenomic and metabolic biomarkers in the folate pathway and their association with methotrexate effects during dosage escalation in rheumatoid arthritis.
2006 Oct
Increased ATP-sensitive K+ channel expression during acute glucose deprivation.
2006 Sep 29
5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside-induced AMP-activated protein kinase phosphorylation inhibits basal and insulin-stimulated glucose uptake, lipid synthesis, and fatty acid oxidation in isolated rat adipocytes.
2006 Sep 8
5-aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside acutely stimulates skeletal muscle 2-deoxyglucose uptake in healthy men.
2007 Aug
Formamide as the main building block in the origin of nucleic acids.
2007 Aug 16
5'-AMP-activated protein kinase activation prevents postischemic leukocyte-endothelial cell adhesive interactions.
2007 Jan
Role of hypothalamic adenosine 5'-monophosphate-activated protein kinase in the impaired counterregulatory response induced by repetitive neuroglucopenia.
2007 Mar
Structural insight into AMPK regulation: ADP comes into play.
2007 Oct
Proteomics analysis of hypothalamic response to energy restriction in dairy cows.
2007 Oct
Adiponectin antagonizes stimulatory effect of tumor necrosis factor-alpha on vascular smooth muscle cell calcification: regulation of growth arrest-specific gene 6-mediated survival pathway by adenosine 5'-monophosphate-activated protein kinase.
2008 Apr
Ethanol consumption impairs regulation of fatty acid metabolism by decreasing the activity of AMP-activated protein kinase in rat liver.
2008 Mar
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:18:03 UTC 2023
Edited
by admin
on Fri Dec 15 16:18:03 UTC 2023
Record UNII
3V0Y2PDE6K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-AMINO-5-IMIDAZOLE CARBOXAMIDE
Systematic Name English
BA-2756
Code English
DACARBAZINE RELATED COMPOUND A (FREE BASE)
USP  
Common Name English
TEMOZOLOMIDE IMPURITY, AMINOIMIDAZOLECARBOXAMIDE [USP IMPURITY]
Common Name English
AIC
Common Name English
5-AMINO-1H-IMIDAZOLE-4-CARBOXAMIDE
Systematic Name English
TEMOZOLOMIDE IMPURITY A [EP IMPURITY]
Common Name English
5-AMINO-4-IMIDAZOLECARBOXAMIDE
Systematic Name English
DACARBAZINE IMPURITY B [EP IMPURITY]
Common Name English
IMIDAZOLE-4-CARBOXAMIDE, 5-AMINO-
Systematic Name English
NSC-7784
Code English
AICA
Common Name English
DACARBAZINE RELATED COMPOUND A (FREE BASE) [USP IMPURITY]
Common Name English
5-AMINOIMIDAZOLE-4-CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
LOINC 79679-7
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
LOINC 79652-4
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
LOINC 79672-2
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
Code System Code Type Description
PUBCHEM
9679
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
CHEBI
2030
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
FDA UNII
3V0Y2PDE6K
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
NSC
7784
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
CAS
360-97-4
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID8059891
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-641-4
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
PARENT -> METABOLITE INACTIVE
Related Record Type Details
PARENT -> IMPURITY
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP