MiMeDB: Showing metabocard for 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide (MMDBc0031790)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:49:25 UTC

Update Date

2022-08-31 18:24:45 UTC

Metabolite ID

MMDBc0031790

Metabolite Identification

Common Name

1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide

Description

1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide is an intermediate in the histidine biosynthesis pathway. It is a substrate for the enzyme 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase which catalyzes the reaction 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide = 5-((5-phospho-1-deoxyribulos-1-ylamino)methylideneamino)-1-(5-phosphoribosyl)imidazole-4-carboxamide

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10101211212D          

 45 47  0  0  0  0            999 V2000
   -0.8482    6.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056    0.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672    3.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689    1.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1838    6.2003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7209    0.5122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2564    3.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908    6.0287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0535    0.0273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0770    5.2082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6139    0.5122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2564    4.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890    2.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    4.8727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3590    1.2968    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9709    4.4713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956    3.0038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518    4.0657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239    2.7489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    1.9642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6038    6.5808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535   -0.7977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7915    4.7957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3986    0.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    4.4713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620    9.1287    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.7513    8.7106    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2439    8.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509   -1.6538    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.6160   -1.7149    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.5120   -0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331    7.6214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771   -0.5497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7713    5.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4660    1.2968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976    8.3750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -1.1018    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    6.6252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8500   -0.3027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627    6.8506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3759   -0.7322    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7689    5.6576    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430   -0.3027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    4.3535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1738    1.1677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  1  0  0  0
  6  2  1  1  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17  3  2  0  0  0  0
 17 13  1  4  0  0  0
 18  3  1  0  0  0  0
 14 18  1  1  0  0  0
 19  4  2  0  0  0  0
 19  7  1  0  0  0  0
 20  4  1  0  0  0  0
 20 13  1  0  0  0  0
 15 20  1  1  0  0  0
  8 21  1  6  0  0  0
  9 22  1  6  0  0  0
 10 23  1  6  0  0  0
 11 24  1  6  0  0  0
 25 12  2  0  0  0  0
 32  1  1  0  0  0  0
 33  2  1  0  0  0  0
 34  5  1  0  0  0  0
 34 14  1  0  0  0  0
 35  6  1  0  0  0  0
 35 15  1  0  0  0  0
 36 26  1  0  0  0  0
 36 27  1  0  0  0  0
 36 28  2  0  0  0  0
 36 32  1  0  0  0  0
 37 29  1  0  0  0  0
 37 30  1  0  0  0  0
 37 31  2  0  0  0  0
 37 33  1  0  0  0  0
  5 38  1  6  0  0  0
  6 39  1  6  0  0  0
  8 40  1  1  0  0  0
  9 41  1  1  0  0  0
 10 42  1  1  0  0  0
 11 43  1  1  0  0  0
 14 44  1  6  0  0  0
 15 45  1  6  0  0  0
M  CHG  4  26  -1  27  -1  29  -1  30  -1
M  END


  Mrv0541 10101211212D          

 45 47  0  0  0  0            999 V2000
   -0.8482    6.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056    0.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3672    3.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689    1.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1838    6.2003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7209    0.5122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2564    3.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908    6.0287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0535    0.0273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0770    5.2082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6139    0.5122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2564    4.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890    2.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    4.8727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3590    1.2968    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9709    4.4713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956    3.0038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518    4.0657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239    2.7489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    1.9642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6038    6.5808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535   -0.7977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7915    4.7957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3986    0.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    4.4713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620    9.1287    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.7513    8.7106    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2439    8.0395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509   -1.6538    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.6160   -1.7149    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.5120   -0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331    7.6214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771   -0.5497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7713    5.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4660    1.2968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976    8.3750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -1.1018    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909    6.6252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8500   -0.3027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627    6.8506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3759   -0.7322    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7689    5.6576    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430   -0.3027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645    4.3535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1738    1.1677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  1  0  0  0
  6  2  1  1  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17  3  2  0  0  0  0
 17 13  1  4  0  0  0
 18  3  1  0  0  0  0
 14 18  1  1  0  0  0
 19  4  2  0  0  0  0
 19  7  1  0  0  0  0
 20  4  1  0  0  0  0
 20 13  1  0  0  0  0
 15 20  1  1  0  0  0
  8 21  1  6  0  0  0
  9 22  1  6  0  0  0
 10 23  1  6  0  0  0
 11 24  1  6  0  0  0
 25 12  2  0  0  0  0
 32  1  1  0  0  0  0
 33  2  1  0  0  0  0
 34  5  1  0  0  0  0
 34 14  1  0  0  0  0
 35  6  1  0  0  0  0
 35 15  1  0  0  0  0
 36 26  1  0  0  0  0
 36 27  1  0  0  0  0
 36 28  2  0  0  0  0
 36 32  1  0  0  0  0
 37 29  1  0  0  0  0
 37 30  1  0  0  0  0
 37 31  2  0  0  0  0
 37 33  1  0  0  0  0
  5 38  1  6  0  0  0
  6 39  1  6  0  0  0
  8 40  1  1  0  0  0
  9 41  1  1  0  0  0
 10 42  1  1  0  0  0
 11 43  1  1  0  0  0
 14 44  1  6  0  0  0
 15 45  1  6  0  0  0
M  CHG  4  26  -1  27  -1  29  -1  30  -1
M  END
> <DATABASE_ID>
MMDBc0031790

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(COP([O-])([O-])=O)O[C@@]([H])(NC=NC2=C(N=CN2[C@]2([H])O[C@]([H])(COP([O-])([O-])=O)[C@@]([H])(O)[C@@]2([H])O)C(N)=O)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C15H25N5O15P2/c16-12(25)7-13(17-3-18-14-10(23)8(21)5(34-14)1-32-36(26,27)28)20(4-19-7)15-11(24)9(22)6(35-15)2-33-37(29,30)31/h3-6,8-11,14-15,21-24H,1-2H2,(H2,16,25)(H,17,18)(H2,26,27,28)(H2,29,30,31)/p-4/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1

> <INCHI_KEY>
QOUSHGMTBIIAHR-KEOHHSTQSA-J

> <FORMULA>
C15H21N5O15P2

> <MOLECULAR_WEIGHT>
573.2993

> <EXACT_MASS>
573.050938051

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
47.37770059166903

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4R,5R)-5-(N'-{4-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}imidamido)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

> <ALOGPS_LOGP>
-1.91

> <JCHEM_LOGP>
-5.499596393332748

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.6873312196662242

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.210523495823332

> <JCHEM_PKA_STRONGEST_BASIC>
6.746165667244012

> <JCHEM_POLAR_SURFACE_AREA>
329.52000000000004

> <JCHEM_REFRACTIVITY>
110.08709999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(N'-{5-carbamoyl-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]imidazol-4-yl}imidamido)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   37  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   38  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    5   32                                                       
CONECT    2    6   33                                                       
CONECT    3   17   18                                                       
CONECT    4   19   20                                                       
CONECT    5    1    8   34   38                                             
CONECT    6    2    9   35   39                                             
CONECT    7   12   13   19                                                  
CONECT    8    5   10   21   40                                             
CONECT    9    6   11   22   41                                             
CONECT   10    8   14   23   42                                             
CONECT   11    9   15   24   43                                             
CONECT   12    7   16   25                                                  
CONECT   13    7   17   20                                                  
CONECT   14   10   18   34   44                                             
CONECT   15   11   20   35   45                                             
CONECT   16   12                                                            
CONECT   17    3   13                                                       
CONECT   18    3   14                                                       
CONECT   19    4    7                                                       
CONECT   20    4   13   15                                                  
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   36                                                            
CONECT   27   36                                                            
CONECT   28   36                                                            
CONECT   29   37                                                            
CONECT   30   37                                                            
CONECT   31   37                                                            
CONECT   32    1   36                                                       
CONECT   33    2   37                                                       
CONECT   34    5   14                                                       
CONECT   35    6   15                                                       
CONECT   36   26   27   28   32                                             
CONECT   37   29   30   31   33                                             
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

Synonyms

Value	Source
1-(5-Phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide	ChEBI
1-(5-Phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide tetraanion	ChEBI
1-(5-Phospho-b-D-ribosyl)-5-[(5-phospho-b-D-ribosylamino)methylideneamino]imidazole-4-carboxamide	Generator
1-(5-Phospho-β-D-ribosyl)-5-[(5-phospho-β-D-ribosylamino)methylideneamino]imidazole-4-carboxamide	Generator
1-(5-Phospho-b-D-ribosyl)-5-[(5-phospho-b-D-ribosylamino)methylideneamino]imidazole-4-carboxamide tetraanion	Generator
1-(5-Phospho-β-D-ribosyl)-5-[(5-phospho-β-D-ribosylamino)methylideneamino]imidazole-4-carboxamide tetraanion	Generator
[(2R,3S,4R,5R)-5-(N'-{4-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}imidamido)-3,4-dihydroxyoxolan-2-yl]methyl phosphoric acid	Generator

Molecular Formula

C₁₅H₂₁N₅O₁₅P₂

Average Mass

573.2993

Monoisotopic Mass

573.050938051

IUPAC Name

[(2R,3S,4R,5R)-5-(N'-{4-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}imidamido)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

Traditional Name

[(2R,3S,4R,5R)-5-(N'-{5-carbamoyl-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]imidazol-4-yl}imidamido)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

CAS Registry Number

Not Available

SMILES

[H][C@]1(COP([O-])([O-])=O)O[C@@]([H])(NC=NC2=C(N=CN2[C@]2([H])O[C@]([H])(COP([O-])([O-])=O)[C@@]([H])(O)[C@@]2([H])O)C(N)=O)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C15H25N5O15P2/c16-12(25)7-13(17-3-18-14-10(23)8(21)5(34-14)1-32-36(26,27)28)20(4-19-7)15-11(24)9(22)6(35-15)2-33-37(29,30)31/h3-6,8-11,14-15,21-24H,1-2H2,(H2,16,25)(H,17,18)(H2,26,27,28)(H2,29,30,31)/p-4/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1

InChI Key

QOUSHGMTBIIAHR-KEOHHSTQSA-J

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 phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
2-heteroaryl carboxamide
Imidazole-4-carbonyl group
Alkyl phosphate
Phosphoric acid ester
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Azole
Heteroaromatic compound
Imidazole
Vinylogous amide
Tetrahydrofuran
Carboxamide group
Secondary alcohol
Primary carboxylic acid amide
Amidine
Carboxylic acid amidine
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Formamidine
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organophosphate oxoanion (CHEBI:58435 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.95 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-5.5	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.21	ChemAxon
pKa (Strongest Basic)	6.75	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	329.52 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	110.09 m³·mol⁻¹	ChemAxon
Polarizability	47.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000090000-2fad1b9d7b9af5cb200f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0000090000-650c453631ebf914e44a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0596-9434810000-8b35471c1d38e7f1907a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000090000-12b5745255550f27fed1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-2000090000-7daea325e825cf6ed2ac	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-005a-9011000000-d828b3df227622e4a8ef	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013431	1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide	5-[(5-phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide	1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino] imidazole-4-carboxamide isomerase	Isomerization	RHEA	34755880
MMDBr0013952	1-(5-phosphoribosyl)-5'-AMP	1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide	Histidine biosynthesis bifunctional protein HisIE	Hydrolysis; Synthesis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	360	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Pig ; Cattle ; River trout ; Turkey ; Sheep ; Chicken ; Human sputum; Human subgingival plaque	Unknown
Bacteria	Cyanobacteria	34	Human
Bacteria	Firmicutes	94	Human feces; Human ; Catfish ; Cattle
Bacteria	Actinobacteria	54	Human ; Human feces; Cattle
Bacteria	Aquificae	3
Archaea/Archaea	Euryarchaeota	29
Eukaryota/Fungi	Ascomycota	11	Human feces; Human saliva; Human supragingival plaque
Bacteria/NULL	Proteobacteria	4	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Pig ; Cattle ; River trout ; Turkey ; Sheep ; Chicken ; Human sputum; Human subgingival plaque	Unknown
Bacteria	Bacteroidetes	11	Human ; Human feces
Bacteria	Spirochaetes	7	Pig ; Human
Archaea/Archaea	Thaumarchaeota	2
Bacteria	Chloroflexi	9
Bacteria	Chlorobi	11
Bacteria	Deinococcus-thermus	4
Bacteria	Dictyoglomi	2
Bacteria	Elusimicrobia	2
Bacteria	Gemmatimonadetes	1
Archaea	Euryarchaeota	4
Archaea/Archaea	nah	1
Bacteria	Verrucomicrobia	1
Archaea/Archaea	Crenarchaeota	4
Bacteria	Planctomycetes	1
Archaea	Crenarchaeota	1
Bacteria	nah	1
Bacteria	Thermotogae	4
Bacteria	Nitrospirae	1
Bacteria	Acidobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

58435

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide (MMDBc0031790)

MOL for #<Metabolite:0x000055d24b2e3678>

3D MOL for #<Metabolite:0x000055d24b2e3678>

3D SDF for #<Metabolite:0x000055d24b2e3678>

3D-SDF for #<Metabolite:0x000055d24b2e3678>

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3D PDB for #<Metabolite:0x000055d24b2e3678>

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Structure for #<Metabolite:0x000055d24b2e3678>

3D Structure for #<Metabolite:0x000055d24b2e3678>