NP-MRD: Showing NP-Card for L-2-Aminoadipate adenylate (NP0087682)

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Record Information

Version

2.0

Created at

2022-05-11 16:56:46 UTC

Updated at

2022-05-11 16:56:46 UTC

NP-MRD ID

NP0087682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-2-Aminoadipate adenylate

Description

L-2-Aminoadipate adenylate, also known as 5-adenylyl-2-aminoadipate or alpha-aminoadipoyl-C6-AMP, belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated. L-2-Aminoadipate adenylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220562D          

 33 35  0  0  1  0            999 V2000
   18.5560  -10.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5560  -11.4459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2705  -11.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9850  -11.4459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9850  -10.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2705  -10.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0990   -9.4014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2785   -9.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9429  -10.0688    0.0000 N   0  0  2  0  0  0  0  0  0  0  0  0
   20.6995  -10.2084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1360  -10.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5229   -9.6883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8084  -10.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9799  -10.9078    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8004  -10.9941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0547   -9.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3873  -10.2502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6336   -9.9146    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0486  -10.7433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8799   -9.5791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2125  -10.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4588   -9.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2987  -10.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7913  -10.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0377   -9.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3702  -10.3627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6165  -10.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4564  -11.1832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9491  -10.5121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5303   -9.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4279  -11.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2129  -11.7085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1360   -9.2235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  1  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 11  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  6  0  0  0
 27 29  1  0  0  0  0
 27 30  2  0  0  0  0
 14 31  1  6  0  0  0
 15 32  1  6  0  0  0
 18 33  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -7.8700    3.2600   -1.3245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4016    2.1681   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2888    1.4412    0.1275 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9071    0.3793    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6138    0.0087    0.9280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    0.6872    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0763    1.7794   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    2.2810   -1.0747 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    1.5359   -0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3217    0.5612    0.1165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393   -0.4501    0.7500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5264    0.0311    1.5506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5444   -0.9098    1.6508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2103   -0.2617    1.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3313    0.2014   -0.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727    0.9469   -0.5632 P   0  0  2  0  0  5  0  0  0  0  0  0
    0.8600    2.4252   -0.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4716    0.2992   -2.0718 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    0.5892    0.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3446   -0.3119    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202   -0.8836   -0.8731 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770   -0.5295    1.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324   -1.5054    0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2739   -1.1969   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1113    0.0116   -0.2593 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0722    0.0843    0.8029 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3153    1.2434   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3971    2.2004    0.4490 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4097    1.4482   -1.4162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8474   -2.0289    0.6798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5224   -3.0386    1.3610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8041   -1.3317   -0.2663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6802   -2.2259   -0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9685    4.1839   -0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1303    3.2264   -2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6670   -0.1584    1.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    1.7012   -0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1586   -1.1341    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220   -1.2813    2.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.6262    1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6156   -0.9640    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239   -0.1745   -2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8225   -0.9991    2.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7565    0.4218    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0222   -1.8474    1.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8690   -2.4559    0.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9238   -2.1115   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013   -1.2174   -1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7443   -0.0060   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0749   -0.7317    1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1705    1.0002    1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7579    1.9980   -2.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9376   -2.3948    0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -2.8015    2.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2553   -0.7128   -0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6021   -3.0766   -0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 16 19  1  1
 16 18  1  0
 16 17  2  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 32  1  0
 32 33  1  0
 32 30  1  0
 30 31  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
 25 27  1  0
 27 29  1  0
 27 28  2  0
 30 13  1  0
  6 10  1  0
  6  7  1  0
 26 50  1  0
 26 51  1  0
 25 49  1  6
 24 47  1  0
 24 48  1  0
 23 45  1  0
 23 46  1  0
 22 43  1  0
 22 44  1  0
 18 42  1  0
 14 40  1  0
 14 41  1  0
 13 39  1  1
 11 38  1  1
 32 55  1  6
 33 56  1  0
 30 53  1  6
 31 54  1  0
  9 37  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
 29 52  1  0
M  END


  Mrv0541 02231220562D          

 33 35  0  0  1  0            999 V2000
   18.5560  -10.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5560  -11.4459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2705  -11.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9850  -11.4459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9850  -10.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2705  -10.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0990   -9.4014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2785   -9.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9429  -10.0688    0.0000 N   0  0  2  0  0  0  0  0  0  0  0  0
   20.6995  -10.2084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1360  -10.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5229   -9.6883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8084  -10.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9799  -10.9078    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8004  -10.9941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0547   -9.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3873  -10.2502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6336   -9.9146    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0486  -10.7433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8799   -9.5791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2125  -10.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4588   -9.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2987  -10.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7913  -10.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0377   -9.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3702  -10.3627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6165  -10.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4564  -11.1832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9491  -10.5121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5303   -9.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4279  -11.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2129  -11.7085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1360   -9.2235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  1  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 11  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  6  0  0  0
 27 29  1  0  0  0  0
 27 30  2  0  0  0  0
 14 31  1  6  0  0  0
 15 32  1  6  0  0  0
 18 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCCC(=O)OP(O)(=O)OCC1OC([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H23N6O10P/c17-7(16(26)27)2-1-3-9(23)32-33(28,29)30-4-8-11(24)12(25)15(31-8)22-6-21-10-13(18)19-5-20-14(10)22/h5-8,11-12,15,24-25H,1-4,17H2,(H,26,27)(H,28,29)(H2,18,19,20)/t7-,8?,11+,12+,15?/m0/s1

> <INCHI_KEY>
POJWEBKSMOTPNS-ILUWSIKFSA-N

> <FORMULA>
C16H23N6O10P

> <MOLECULAR_WEIGHT>
490.3618

> <EXACT_MASS>
490.121327498

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
43.508189926222315

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-6-[({[(3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-6-oxohexanoic acid

> <ALOGPS_LOGP>
-2.24

> <JCHEM_LOGP>
-6.671424669928353

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.82627157183639

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.7792957754696692

> <JCHEM_PKA_STRONGEST_BASIC>
9.525621132305863

> <JCHEM_POLAR_SURFACE_AREA>
255.45999999999998

> <JCHEM_REFRACTIVITY>
106.46499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-6-({[(3S,4R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-6-oxohexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      34.638 -19.826   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      34.638 -21.366   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      35.972 -22.136   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      37.305 -21.366   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      37.305 -19.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.972 -19.056   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      35.651 -17.549   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      34.120 -17.388   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      33.493 -18.795   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      38.639 -19.056   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      31.987 -19.115   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      30.843 -18.085   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      29.509 -18.855   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.829 -20.361   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.361 -20.522   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.102 -18.229   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      26.856 -19.134   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0      25.449 -18.507   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0      24.357 -20.054   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      24.042 -17.881   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      22.797 -18.786   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.390 -18.160   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.958 -20.318   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.144 -19.065   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.737 -18.439   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.491 -19.344   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.084 -18.717   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      17.652 -20.875   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0      14.838 -19.623   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      15.923 -17.186   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      28.799 -21.506   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      32.131 -21.856   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      26.387 -17.217   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    1   11                                                  
CONECT   10    5                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14   11   32                                                  
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   33                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   24                                                       
CONECT   23   21                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   29   30                                                  
CONECT   28   26                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   18                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
L-2-Aminoadipic acid adenylic acid	Generator
5-Adenylyl-2-aminoadipate	HMDB
alpha-Aminoadipoyl-C6-AMP	HMDB
(2S)-2-Amino-6-[({[(3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-6-oxohexanoate	HMDB

Chemical Formula

C₁₆H₂₃N₆O₁₀P

Average Mass

490.3618 Da

Monoisotopic Mass

490.12133 Da

IUPAC Name

(2S)-2-amino-6-[({[(3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-6-oxohexanoic acid

Traditional Name

(2S)-2-amino-6-({[(3S,4R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-6-oxohexanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCCC(=O)OP(O)(=O)OCC1OC([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O

InChI Identifier

InChI=1S/C16H23N6O10P/c17-7(16(26)27)2-1-3-9(23)32-33(28,29)30-4-8-11(24)12(25)15(31-8)22-6-21-10-13(18)19-5-20-14(10)22/h5-8,11-12,15,24-25H,1-4,17H2,(H,26,27)(H,28,29)(H2,18,19,20)/t7-,8?,11+,12+,15?/m0/s1

InChI Key

POJWEBKSMOTPNS-ILUWSIKFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

5'-acylphosphoadenosines

Alternative Parents

Substituents

5'-acylphosphoadenosine
Pentose phosphate
Pentose-5-phosphate
N-glycosyl compound
Glycosyl compound
6-aminopurine
Monosaccharide phosphate
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Pentose monosaccharide
Imidazopyrimidine
Purine
Medium-chain fatty acid
Hydroxy fatty acid
Acyl phosphate
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Fatty acyl
Phosphoric acid ester
Dicarboxylic acid or derivatives
Fatty acid
Pyrimidine
Azole
Heteroaromatic compound
Tetrahydrofuran
Imidazole
1,2-diol
Carboxylic acid salt
Amino acid
Amino acid or derivatives
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Organic salt
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

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	-2.2	ALOGPS
logP	-6.7	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.78	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	255.46 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	106.46 m³·mol⁻¹	ChemAxon
Polarizability	43.51 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

External Links

HMDB ID

HMDB0006941

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024157

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05560

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for L-2-Aminoadipate adenylate (NP0087682)

MOL for NP0087682 (L-2-Aminoadipate adenylate)

3D MOL for NP0087682 (L-2-Aminoadipate adenylate)

3D SDF for NP0087682 (L-2-Aminoadipate adenylate)

3D-SDF for NP0087682 (L-2-Aminoadipate adenylate)

PDB for NP0087682 (L-2-Aminoadipate adenylate)

3D PDB for NP0087682 (L-2-Aminoadipate adenylate)

SMILES for NP0087682 (L-2-Aminoadipate adenylate)

INCHI for NP0087682 (L-2-Aminoadipate adenylate)

Structure for NP0087682 (L-2-Aminoadipate adenylate)

3D Structure for NP0087682 (L-2-Aminoadipate adenylate)