5-Aminoimidazole-4-carboxamide

Details

• Internal ID: 42b39c03-0f05-41d3-8614-787423603810
• Taxonomy: Organoheterocyclic compounds > Azoles > Imidazoles > Substituted imidazoles > Aminoimidazoles
• IUPAC Name: 4-amino-1H-imidazole-5-carboxamide
• SMILES (Canonical): C1=NC(=C(N1)C(=O)N)N
• SMILES (Isomeric): C1=NC(=C(N1)C(=O)N)N
• InChI: InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
• InChI Key: DVNYTAVYBRSTGK-UHFFFAOYSA-N
• Popularity: 2,967 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₆N₄O
• Molecular Weight: 126.12 g/mol
• Exact Mass: 126.05416083 g/mol
• Topological Polar Surface Area (TPSA): 97.80 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.91
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 5-Aminoimidazole-4-carboxamide
• 4-Amino-1H-imidazole-5-carboxamide
• 4-Amino-5-imidazolecarboxamide
• 5-amino-1H-imidazole-4-carboxamide
• 5-Amino-4-imidazolecarboxamide
• AICA
• 21299-72-9
• Colahepat
• 4-Aminoimidazole-5-carboxamide
• Aminoimidazole carboxamide
• 1H-Imidazole-4-carboxamide, 5-amino-
• 5-amino-3H-imidazole-4-carboxamide
• Diazol-C
• 4-Carbamoyl-5-aminoimidazole
• 5-Aminoimidazol-4-carboxamide
• 4-Carboxamido-5-aminoimidazole
• Ba 2756
• IMIDAZOLE-4-CARBOXAMIDE, 5-AMINO-
• 5-amino-imidazole-4-carboxamide
• 4-Amino-5-imidazole carboxamide
• 5-Imidazolecarboxamide, 4-amino-
• 5-Aminoimidazolecarboxamide
• NSC 7784
• 5-Aminoimidazole carboxamide
• 4-amino-5-carbamoylimidazole
• AIC
• NSC-7784
• EINECS 206-641-4
• UNII-3V0Y2PDE6K
• 3V0Y2PDE6K
• CHEBI:2030
• IMIDAZOLE-4(OR 5)-CARBOXAMIDE, 5(OR 4)-AMINO-
• 5-Amino-4-imidazolecarboxyamide
• 4(5)-Amino-5(4)-Imidazolecarboxamide
• MFCD02181040
• Imidazole-4-carboxamide, 5-amino- (hydrochloride)
• Dacarbazine impurity B
• SCHEMBL8024
• CHEMBL1610
• MLS000701328
• Imidazole C-4,5 deriv. 2
• WLN: T5M CNJ DVZ EZ
• BDBM7957
• DTXSID8059891
• DVNYTAVYBRSTGK-UHFFFAOYSA-
• NSC7784
• Aminoimidazole-4-carboxamide, 5-
• Imidazole, 5-amino-4-carboxamide
• HMS2231D11
• HMS3369A01
• 5-amino-1H-imidazole4-carboxamide
• BCP22943
• 5-amino-1 H-imidazole4-carboxamide
• 4-azanyl-1H-imidazole-5-carboxamide
• Imidazole, 4-amino-5-aminocarbonyl-
• s3651
• STL484285
• 5-amino-1 H-imidazole-4-carboxamide
• 4-Amino-5-Imidazolecarboxamide(AICA)
• 5-Amino-4-imidazolecarboxamide, 95%
• AKOS009084625
• AKOS015855671
• 5-Amino-1H-imidazole-4-carboxamide #
• AC-8311
• BA-2756
• CCG-266103
• CS-W019921
• NCGC00245975-01
• NCGC00245975-02
• AS-12404
• HY-41461
• LS-78157
• SMR000526285
• SY009547
• AM20090183
• AM20090571
• DACARBAZINE IMPURITY B [EP IMPURITY]
• FT-0632037
• TEMOZOLOMIDE IMPURITY A [EP IMPURITY]
• 4-Amino-5-carboxamido imidazole hydrochloride
• 5-amino-1H-imidazole-4-carboxylic acid amide
• 5-Amino-3H-imidazole-4-carboxylic acid amide
• EN300-23736
• C04051
• O11342
• W13853
• A815255
• A823125
• AG-756/20213048
• Q-200531
• 5-Amino-2-methyl-n-ethyl-n-phenyl-benzenesulfonamide
• Q27067435
• 4-Amino-5-imidazolecarboxamide hydrochloride (Salt/Mix)
• F0001-1035
• 49B332E5-7C8B-4C28-9FDF-05F173231B6A
• Dacarbazine impurity B, European Pharmacopoeia (EP) Reference Standard
• TEMOZOLOMIDE IMPURITY, AMINOIMIDAZOLECARBOXAMIDE [USP IMPURITY]
• InChI=1/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
• 5AC

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	-	0.5622	56.22%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Lysosomes	0.3986	39.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9774	97.74%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9283	92.83%
P-glycoprotein inhibitior	-	0.9876	98.76%
P-glycoprotein substrate	-	0.9395	93.95%
CYP3A4 substrate	-	0.7610	76.10%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.9017	90.17%
CYP3A4 inhibition	-	0.9088	90.88%
CYP2C9 inhibition	-	0.8713	87.13%
CYP2C19 inhibition	-	0.7193	71.93%
CYP2D6 inhibition	-	0.9434	94.34%
CYP1A2 inhibition	+	0.7191	71.91%
CYP2C8 inhibition	-	0.9543	95.43%
CYP inhibitory promiscuity	-	0.7914	79.14%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.4657	46.57%
Eye corrosion	-	0.9777	97.77%
Eye irritation	+	0.8751	87.51%
Skin irritation	-	0.7680	76.80%
Skin corrosion	-	0.9620	96.20%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7778	77.78%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.9252	92.52%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6587	65.87%
Acute Oral Toxicity (c)	III	0.5791	57.91%
Estrogen receptor binding	-	0.9546	95.46%
Androgen receptor binding	-	0.8638	86.38%
Thyroid receptor binding	-	0.6316	63.16%
Glucocorticoid receptor binding	-	0.9031	90.31%
Aromatase binding	-	0.8148	81.48%
PPAR gamma	-	0.8670	86.70%
Honey bee toxicity	-	0.9577	95.77%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.9254	92.54%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3129	Q9Y2T3	Guanine deaminase	4440 nM	Ki	PMID: 20716488

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.74%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.52%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.80%	91.11%
CHEMBL4208	P20618	Proteasome component C5	84.86%	90.00%
CHEMBL3835	P51955	Serine/threonine-protein kinase NEK2	84.39%	80.33%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	83.74%	95.48%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.80%	95.56%

Plants that contains it

• Pogostemon cablin

Cross-Links

• PubChem: 9679
• NPASS: NPC293163
• ChEMBL: CHEMBL1610
• LOTUS: LTS0145499
• wikiData: Q27067435