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Showing metabocard for AICAR (HMDB0001517)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 18:34:15 UTC
HMDB IDHMDB0001517
Secondary Accession Numbers
  • HMDB01517
Metabolite Identification
Common NameAICAR
DescriptionAICAR, also known as Z-nucleotide or ZMP, 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. AICAR is a strong basic compound (based on its pKa). AICAR exists in all living species, ranging from bacteria to humans. Within humans, AICAR participates in a number of enzymatic reactions. In particular, fumaric acid and AICAR can be biosynthesized from SAICAR; which is catalyzed by the enzyme adenylosuccinate lyase. In addition, 10-formyltetrahydrofolate and AICAR can be converted into tetrahydrofolic acid and phosphoribosyl formamidocarboxamide; which is mediated by the enzyme bifunctional purine biosynthesis protein purh. In humans, AICAR is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. Outside of the human body, AICAR has been detected, but not quantified in, several different foods, such as cardoons, chayotes, almonds, buffalo currants, and rambutans. This could make AICAR a potential biomarker for the consumption of these foods. AICAR has been used clinically to treat and protect against cardiac ischemic injury. The drug was first used in the 1980s as a method to preserve blood flow to the heart during surgery and is currently of interest as a potential treatment for diabetes by increasing the metabolic activity of tissues by changing the physical composition of muscle. 5-Aminoimidazole-4-carboxamide ribonucleotide is an intermediate in the generation of inosine monophosphate and analog of adenosine monophosphate (AMP) that is capable of stimulating AMP-dependent protein kinase (AMPK) activity.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001517 (AICAR)

  Mrv1652309122018102D          

 22 23  0  0  0  0            999 V2000
10001.7525 9999.2289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.152210000.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.868710000.5597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.1522 9999.3209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5901 9998.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.330910000.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7981 9998.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.615710000.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.900310000.5597    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.312410001.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.181210000.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.486610001.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.711810000.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.044410000.1558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2993 9999.3712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.1243 9999.3712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.379210000.1558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.771510000.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.104110000.5505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.359010001.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.184010001.3351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.438910000.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 22  2  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
  1 18  1  0  0  0  0
 22  2  1  0  0  0  0
 17 19  1  1  0  0  0
 16  5  1  6  0  0  0
 14  6  1  1  0  0  0
 15  7  1  6  0  0  0
M  END
Download

3D MOL for HMDB0001517 (AICAR)

HMDB0001517
     RDKit          3D
AICAR
 37 38  0  0  0  0  0  0  0  0999 V2000
    5.2176    0.5394    2.6803 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7671    0.4794    1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860    0.5022    0.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3400    0.3899    1.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2956    0.3516    1.8995 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1455    0.2680    1.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4228    0.2503   -0.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774    0.1672   -1.2157 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6969    0.7782   -0.8795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479   -0.0620   -1.1420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9520    0.2549   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6490    0.1311    1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0575    0.5061    1.9316 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.9544    0.0819    3.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3381   -0.3129    1.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2645    2.1839    1.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1893   -1.4359   -0.8407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8398   -2.4301   -1.5629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134   -1.2951   -1.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1976   -1.6190   -2.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651    0.3241   -0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    0.3348   -1.4317 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0957    1.0382    2.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    0.0894    3.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1236    0.2194    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111    0.5985   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833   -0.0499   -2.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806   -0.4271   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2615    1.2853   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6261    0.1975    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517    2.4583    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1189   -1.6537    0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9957   -2.0547   -2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348   -1.9543   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908   -0.8037   -3.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9540   -0.5342   -1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568    1.2031   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 10 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7 21  1  0
 21 22  1  0
 21  4  2  0
 19  8  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  6
 10 27  1  6
 11 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  1
 18 33  1  0
 19 34  1  1
 20 35  1  0
 22 36  1  0
 22 37  1  0
M  END
Download

3D SDF for HMDB0001517 (AICAR)

  Mrv1652309122018102D          

 22 23  0  0  0  0            999 V2000
10001.7525 9999.2289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.152210000.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.868710000.5597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.1522 9999.3209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5901 9998.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.330910000.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7981 9998.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.615710000.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.900310000.5597    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.312410001.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.181210000.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.486610001.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.711810000.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.044410000.1558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2993 9999.3712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.1243 9999.3712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.379210000.1558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.771510000.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.104110000.5505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.359010001.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.184010001.3351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.438910000.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 22  2  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
  1 18  1  0  0  0  0
 22  2  1  0  0  0  0
 17 19  1  1  0  0  0
 16  5  1  6  0  0  0
 14  6  1  1  0  0  0
 15  7  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001517

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1

> <INCHI_KEY>
NOTGFIUVDGNKRI-UUOKFMHZSA-N

> <FORMULA>
C9H15N4O8P

> <MOLECULAR_WEIGHT>
338.2112

> <EXACT_MASS>
338.062749988

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.56573109900927

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-2.16

> <JCHEM_LOGP>
-4.81241299868757

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.266347985457528

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2245998962218518

> <JCHEM_PKA_STRONGEST_BASIC>
4.804279678031426

> <JCHEM_POLAR_SURFACE_AREA>
203.37999999999997

> <JCHEM_REFRACTIVITY>
69.1421

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aica ribonucleotide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001517 (AICAR)

HMDB0001517
     RDKit          3D
AICAR
 37 38  0  0  0  0  0  0  0  0999 V2000
    5.2176    0.5394    2.6803 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7671    0.4794    1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860    0.5022    0.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3400    0.3899    1.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2956    0.3516    1.8995 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1455    0.2680    1.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4228    0.2503   -0.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774    0.1672   -1.2157 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6969    0.7782   -0.8795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479   -0.0620   -1.1420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9520    0.2549   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6490    0.1311    1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0575    0.5061    1.9316 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.9544    0.0819    3.3855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3381   -0.3129    1.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2645    2.1839    1.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1893   -1.4359   -0.8407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8398   -2.4301   -1.5629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134   -1.2951   -1.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1976   -1.6190   -2.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651    0.3241   -0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    0.3348   -1.4317 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0957    1.0382    2.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    0.0894    3.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1236    0.2194    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111    0.5985   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0833   -0.0499   -2.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806   -0.4271   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2615    1.2853   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6261    0.1975    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517    2.4583    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1189   -1.6537    0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9957   -2.0547   -2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348   -1.9543   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908   -0.8037   -3.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9540   -0.5342   -1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568    1.2031   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 10 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  7 21  1  0
 21 22  1  0
 21  4  2  0
 19  8  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  6
 10 27  1  6
 11 28  1  0
 11 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  1
 18 33  1  0
 19 34  1  1
 20 35  1  0
 22 36  1  0
 22 37  1  0
M  END
Download

PDB for HMDB0001517 (AICAR)

HEADER    PROTEIN                                 12-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-20         0                                  
HETATM    1  N   UNK     0    8669.9388665.227   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    8672.5518666.941   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8673.8888667.711   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0    8672.5518665.399   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.7688664.236   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8663.5518667.711   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8664.4238664.252   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8662.2168666.941   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0    8660.8818667.711   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0    8661.6508669.049   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8659.5388666.937   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8660.1088669.049   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8666.1298667.863   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8664.8838666.957   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3598665.493   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.8998665.493   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3758666.957   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.9738666.789   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8668.7288667.694   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8669.2038669.159   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0    8670.7438669.159   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0    8671.2198667.694   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2    3    4   22                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5   16                                                            
CONECT    6    8   14                                                       
CONECT    7   15                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   14   17                                                       
CONECT   14   15   13    6                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17    5                                                  
CONECT   17   16   13   19                                                  
CONECT   18   22   19    1                                                  
CONECT   19   18   20   17                                                  
CONECT   20   21   19                                                       
CONECT   21   20   22                                                       
CONECT   22   18   21    2                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END
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3D PDB for HMDB0001517 (AICAR)

COMPND    HMDB0001517
HETATM    1  N1  UNL     1       5.218   0.539   2.680  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.767   0.479   1.353  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.586   0.502   0.413  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.340   0.390   1.056  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.296   0.352   1.899  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.146   0.268   1.212  1.00  0.00           C  
HETATM    7  N3  UNL     1       1.423   0.250  -0.094  1.00  0.00           N  
HETATM    8  C4  UNL     1       0.477   0.167  -1.216  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.697   0.778  -0.879  1.00  0.00           O  
HETATM   10  C5  UNL     1      -1.748  -0.062  -1.142  1.00  0.00           C  
HETATM   11  C6  UNL     1      -2.952   0.255  -0.285  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.649   0.131   1.081  1.00  0.00           O  
HETATM   13  P1  UNL     1      -4.057   0.506   1.932  1.00  0.00           P  
HETATM   14  O4  UNL     1      -3.954   0.082   3.386  1.00  0.00           O  
HETATM   15  O5  UNL     1      -5.338  -0.313   1.196  1.00  0.00           O  
HETATM   16  O6  UNL     1      -4.265   2.184   1.846  1.00  0.00           O  
HETATM   17  C7  UNL     1      -1.189  -1.436  -0.841  1.00  0.00           C  
HETATM   18  O7  UNL     1      -1.840  -2.430  -1.563  1.00  0.00           O  
HETATM   19  C8  UNL     1       0.213  -1.295  -1.443  1.00  0.00           C  
HETATM   20  O8  UNL     1       0.198  -1.619  -2.792  1.00  0.00           O  
HETATM   21  C9  UNL     1       2.765   0.324  -0.218  1.00  0.00           C  
HETATM   22  N4  UNL     1       3.495   0.335  -1.432  1.00  0.00           N  
HETATM   23  H1  UNL     1       6.096   1.038   2.942  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.699   0.089   3.473  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.124   0.219   1.603  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.911   0.599  -2.129  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.083  -0.050  -2.194  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.781  -0.427  -0.525  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.261   1.285  -0.478  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.626   0.197   0.404  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.552   2.458   0.948  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.119  -1.654   0.227  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.996  -2.055  -2.484  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.935  -1.954  -0.901  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.091  -0.804  -3.308  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.954  -0.534  -1.750  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.557   1.203  -1.976  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3    3    4
CONECT    4    5   21   21
CONECT    5    6    6
CONECT    6    7   25
CONECT    7    8   21
CONECT    8    9   19   26
CONECT    9   10
CONECT   10   11   17   27
CONECT   11   12   28   29
CONECT   12   13
CONECT   13   14   14   15   16
CONECT   15   30
CONECT   16   31
CONECT   17   18   19   32
CONECT   18   33
CONECT   19   20   34
CONECT   20   35
CONECT   21   22
CONECT   22   36   37
END
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SMILES for HMDB0001517 (AICAR)

NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
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INCHI for HMDB0001517 (AICAR)

InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC9H15N4O8P
Average Molecular Weight338.2112
Monoisotopic Molecular Weight338.062749988
IUPAC Name{[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Nameaica ribonucleotide
CAS Registry Number3031-94-5
SMILES
NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
InChI KeyNOTGFIUVDGNKRI-UUOKFMHZSA-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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub Class1-ribosyl-imidazolecarboxamides
Direct Parent1-ribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-ribosyl-imidazolecarboxamide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • 2-heteroaryl carboxamide
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • Aminoimidazole
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Primary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-diol
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Primary amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available167.615http://allccs.zhulab.cn/database/detail?ID=AllCCS00000126
[M+H]+Not Available172.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00000126
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue Locations
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.441 +/- 0.133 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.504 +/- 0.126 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.548 +/- 0.153 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01700
Phenol Explorer Compound IDNot Available
FooDB IDFDB030675
KNApSAcK IDC00007383
Chemspider ID58620
KEGG Compound IDC04677
BioCyc IDAICAR
BiGG ID44312
Wikipedia LinkAICA_ribonucleotide
METLIN ID6294
PubChem Compound65110
PDB IDNot Available
ChEBI ID18406
Food Biomarker OntologyNot Available
VMH IDAICAR
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSchmitt, Laurent; Caperelli, Carol A. Enantiospecific synthesis of carbocyclic aminoimidazole carboxamide ribonucleotide (C-AICAR), succinoaminoimidazole carboxamide ribonucleotide (C-SAICAR), and a new intermediate for SAICAR analogs. Nucleosides & Nucleotides (1995), 14(9 & 10), 1929-45.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jakobsen SN, Hardie DG, Morrice N, Tornqvist HE: 5'-AMP-activated protein kinase phosphorylates IRS-1 on Ser-789 in mouse C2C12 myotubes in response to 5-aminoimidazole-4-carboxamide riboside. J Biol Chem. 2001 Dec 14;276(50):46912-6. Epub 2001 Oct 11. [PubMed:11598104 ]
  2. Koistinen HA, Galuska D, Chibalin AV, Yang J, Zierath JR, Holman GD, Wallberg-Henriksson H: 5-amino-imidazole carboxamide riboside increases glucose transport and cell-surface GLUT4 content in skeletal muscle from subjects with type 2 diabetes. Diabetes. 2003 May;52(5):1066-72. [PubMed:12716734 ]
  3. Koistinen HA, Chibalin AV, Zierath JR: Aberrant p38 mitogen-activated protein kinase signalling in skeletal muscle from Type 2 diabetic patients. Diabetologia. 2003 Oct;46(10):1324-8. Epub 2003 Aug 23. [PubMed:12937895 ]

Enzymes

Enzyme Details
1. Adenine phosphoribosyltransferase
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
Reactions
AICAR + Pyrophosphate → 5-Aminoimidazole-4-carboxamide + Phosphoribosyl pyrophosphatedetails
Enzyme Details
2. Adenylosuccinate lyase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ADSL
Uniprot ID:
P30566
Molecular weight:
54888.735
Reactions
SAICAR → Fumaric acid + AICARdetails
SAICAR → Fumaric acid + AICARdetails
Enzyme Details
3. Bifunctional purine biosynthesis protein PURH
General function:
Involved in IMP cyclohydrolase activity
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
P31939
Molecular weight:
64615.255
Reactions
10-Formyltetrahydrofolate + AICAR → Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamidedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]