NP-MRD: Showing NP-Card for 3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid (NP0324755)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...Show more...

Record Information

Version

2.0

Created at

2022-09-12 05:01:34 UTC

Updated at

2022-09-12 05:01:34 UTC

NP-MRD ID

NP0324755

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid

Description

Deferoxamine, also known as DFO or DF b, belongs to the class of organic compounds known as acetohydroxamic acids. These are organic compounds that contain a hydroxamic acid group carrying a methyl group attached to its carbon center. Thus, deferoxamine is considered to be a fatty amide lipid molecule. Deferoxamine is a drug which is used to treat acute iron or aluminum toxicity (an excess of aluminum in the body) in certain patients. Also used in certain patients with anemia who must receive many blood transfusions. Deferoxamine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It is unclear if use during pregnancy or breastfeeding is safe for the baby. It is used by injection into a muscle, vein, or under the skin. 3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid is found in Streptomyces albidoflavus, Streptomyces argillaceus, Streptomyces coelicolor, Streptomyces griseus, Streptomyces hebeiensis, Streptomyces lydicus, Streptomyces malaysiense, Streptomyces mirabilis, Streptomyces parvulus, Streptomyces pilosus and Streptomyces wadayamensis. Apart from iron toxicity, deferoxamine can be used to treat aluminium toxicity (an excess of aluminium in the body) in select patients.

Structure

MOL 3D MOL SDF PDB SMILES InChI

746
  Mrv0541 02231214582D          

 39 38  0  0  0  0            999 V2000
   14.2380   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9524    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2371    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0957   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0966    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0938   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8111   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2380   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9515   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8101    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0966    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8091   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3804   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9534   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5236    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2389    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6678    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5245   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3822   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6668   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3812    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5226   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8082    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9524    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2371    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0957   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0938   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8111   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5255    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 12  1  0  0  0  0
  3 33  2  0  0  0  0
  4 34  2  0  0  0  0
  5 35  2  0  0  0  0
  6 13  1  0  0  0  0
  7 37  2  0  0  0  0
  8 38  2  0  0  0  0
  9 19  1  0  0  0  0
  9 33  1  0  0  0  0
 10 21  1  0  0  0  0
 10 34  1  0  0  0  0
 11 25  1  0  0  0  0
 11 35  1  0  0  0  0
 12 26  1  0  0  0  0
 12 37  1  0  0  0  0
 13 28  1  0  0  0  0
 13 38  1  0  0  0  0
 14 36  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  1  0  0  0  0
 18 20  1  0  0  0  0
 18 22  1  0  0  0  0
 20 25  1  0  0  0  0
 22 28  1  0  0  0  0
 23 24  1  0  0  0  0
 23 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 36  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  0  0  0  0
 32 37  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

 87 86  0  0  0  0  0  0  0  0999 V2000
   12.5746    2.3766    1.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5898    2.6706    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4148    3.8901    0.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9571    1.6137   -0.1234 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2701    0.3388    0.2942 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0208    1.6614   -1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5719    1.7457   -0.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3248    0.6273    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8906    0.5204    0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3553    1.8057    1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0335    1.6419    1.6881 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9507    1.1447    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1777    0.7895   -0.2637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    0.9922    1.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -0.0030    0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326    0.3755   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279    1.5751   -1.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -0.6216   -1.7045 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1795   -0.2653   -3.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0749   -1.9752   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4196   -2.1411   -0.9771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6643   -3.4993   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1308   -3.7255   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8723   -3.7915   -1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2926   -3.9990   -1.2872 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1541   -3.0708   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7265   -2.0183   -0.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6329   -3.3629   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3754   -2.1160   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8258   -2.2539   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3266   -3.4085    0.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7136   -1.1349   -0.1252 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0285   -1.3443    0.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2074    0.2052   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8763    0.8596    0.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2939    2.2456    0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0034    2.2257   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4848    3.6250   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3466    4.5032   -0.9196 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9050    1.3178    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0026    2.4167    2.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4115    3.0841    1.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6002   -0.1175   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2108    0.8635   -1.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2342    2.6360   -1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9623    1.6283   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4098    2.7396   -0.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9882    0.7403    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6124   -0.3216   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3166    0.0327   -0.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8544   -0.2222    1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9942    2.3088    1.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2909    2.5847    0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8575    1.9181    2.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6874    0.5567    2.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448    1.9516    1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779   -1.0129    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7133   -0.0649    1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1945   -1.0647   -3.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7044   -2.2164   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3108   -2.6872   -2.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079   -1.3708   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -1.9782   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126   -4.3237   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504   -3.5350    0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -2.8595    0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116   -4.6820    0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455   -2.8871   -2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4398   -4.6498   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130   -4.8597   -1.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9873   -3.8116   -1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7470   -4.0766    0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9630   -1.6997    0.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1127   -1.3383   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1220   -2.0495    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4114    0.1708   -1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0407    0.8004   -0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2048    0.2203    1.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8191    0.9324    1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1577    2.6982    1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0241    2.8612    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2078    1.6988    0.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1048    1.7127   -0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1606    4.1045    0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5247    3.5662   -0.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5166    5.4338   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8756    4.1481   -1.7089 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
  4  6  1  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  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
  7 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  0
  9 51  1  0
 10 52  1  0
 10 53  1  0
 11 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  0
 23 67  1  0
 24 68  1  0
 24 69  1  0
 25 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 33 75  1  0
 34 76  1  0
 34 77  1  0
 35 78  1  0
 35 79  1  0
 36 80  1  0
 36 81  1  0
 37 82  1  0
 37 83  1  0
 38 84  1  0
 38 85  1  0
 39 86  1  0
 39 87  1  0
M  END

746
  Mrv0541 02231214582D          

 39 38  0  0  0  0            999 V2000
   14.2380   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9524    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2371    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0957   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0966    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0938   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8111   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2380   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9515   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8101    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0966    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8091   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3804   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9534   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5236    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2389    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6678    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5245   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3822   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6668   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3812    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5226   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8082    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9524    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2371    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0957   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0938   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8111   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5255    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 12  1  0  0  0  0
  3 33  2  0  0  0  0
  4 34  2  0  0  0  0
  5 35  2  0  0  0  0
  6 13  1  0  0  0  0
  7 37  2  0  0  0  0
  8 38  2  0  0  0  0
  9 19  1  0  0  0  0
  9 33  1  0  0  0  0
 10 21  1  0  0  0  0
 10 34  1  0  0  0  0
 11 25  1  0  0  0  0
 11 35  1  0  0  0  0
 12 26  1  0  0  0  0
 12 37  1  0  0  0  0
 13 28  1  0  0  0  0
 13 38  1  0  0  0  0
 14 36  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  1  0  0  0  0
 18 20  1  0  0  0  0
 18 22  1  0  0  0  0
 20 25  1  0  0  0  0
 22 28  1  0  0  0  0
 23 24  1  0  0  0  0
 23 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 36  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  0  0  0  0
 32 37  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324755

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN

> <INCHI_IDENTIFIER>
InChI=1S/C25H48N6O8/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34)

> <INCHI_KEY>
UBQYURCVBFRUQT-UHFFFAOYSA-N

> <FORMULA>
C25H48N6O8

> <MOLECULAR_WEIGHT>
560.684

> <EXACT_MASS>
560.353362542

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
62.40535254154213

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
-3.3651618260693423

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.390588453904945

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.915494126454605

> <JCHEM_PKA_STRONGEST_BASIC>
10.225199409093682

> <JCHEM_POLAR_SURFACE_AREA>
205.84000000000003

> <JCHEM_REFRACTIVITY>
144.9508

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]succinamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 746                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      26.578  -1.925   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.908   1.925   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      27.911   1.925   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.243   1.925   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      31.912  -1.925   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      41.247   1.925   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.242  -1.925   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      42.581  -1.925   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      26.578  -0.385   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      18.576  -0.385   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      33.245   0.385   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      11.908   0.385   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      41.247   0.385   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       3.907   0.385   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      22.577   0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.910  -0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.243  -0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.246  -0.385   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.244   0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.913   0.385   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.910   0.385   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.580   0.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.241   0.385   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.907  -0.385   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      34.579  -0.385   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.575  -0.385   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      39.913  -0.385   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      29.245  -0.385   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.578   0.385   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.909  -0.385   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.575   0.385   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      27.911   0.385   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.243   0.385   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      31.912  -0.385   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.240  -0.385   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.242  -0.385   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      42.581  -0.385   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      43.914   0.385   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   12                                                            
CONECT    3   33                                                            
CONECT    4   34                                                            
CONECT    5   35                                                            
CONECT    6   13                                                            
CONECT    7   37                                                            
CONECT    8   38                                                            
CONECT    9    1   19   33                                                  
CONECT   10   21   34                                                       
CONECT   11   25   35                                                       
CONECT   12    2   26   37                                                  
CONECT   13    6   28   38                                                  
CONECT   14   36                                                            
CONECT   15   16   17                                                       
CONECT   16   15   19                                                       
CONECT   17   15   21                                                       
CONECT   18   20   22                                                       
CONECT   19    9   16                                                       
CONECT   20   18   25                                                       
CONECT   21   10   17                                                       
CONECT   22   18   28                                                       
CONECT   23   24   26                                                       
CONECT   24   23   27                                                       
CONECT   25   11   20                                                       
CONECT   26   12   23                                                       
CONECT   27   24   36                                                       
CONECT   28   13   22                                                       
CONECT   29   30   33                                                       
CONECT   30   29   35                                                       
CONECT   31   32   34                                                       
CONECT   32   31   37                                                       
CONECT   33    3    9   29                                                  
CONECT   34    4   10   31                                                  
CONECT   35    5   11   30                                                  
CONECT   36   14   27                                                       
CONECT   37    7   12   32                                                  
CONECT   38    8   13   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   76    0
END

View in JSmol

Synonyms

Value	Source
Deferoxamin	ChEBI
Deferoxamina	ChEBI
Deferoxaminum	ChEBI
Deferrioxamine	ChEBI
Deferrioxamine b	ChEBI
Desferrioxamine	ChEBI
DFO	ChEBI
Deferoxamide b	HMDB
Deferoxamine b	HMDB
Desferrioxamine b	HMDB
DF b	HMDB
DFOA	HMDB
DFOM	HMDB
N-Benzoylferrioxamine b	HMDB
b, Deferoxamine	HMDB
Deferoxamine mesylate	HMDB
Deferoximine	HMDB
Desferioximine	HMDB
Desferrioxamine b mesylate	HMDB
Mesylate, deferoxamine	HMDB
Deferoxamine methanesulfonate	HMDB
Mesylate, desferrioxamine b	HMDB
Methanesulfonate, deferoxamine	HMDB
b, Desferrioxamine	HMDB
Desferal	HMDB
Mesilate, deferoxamine	HMDB
Deferoxamine mesilate	HMDB
Desferroxamine	HMDB

Chemical Formula

C₂₅H₄₈N₆O₈

Average Mass

560.6840 Da

Monoisotopic Mass

560.35336 Da

IUPAC Name

N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide

Traditional Name

N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]succinamide

CAS Registry Number

Not Available

SMILES

CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN

InChI Identifier

InChI=1S/C25H48N6O8/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34)

InChI Key

UBQYURCVBFRUQT-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces albidoflavus	LOTUS Database	35616633
Streptomyces argillaceus	LOTUS Database	35616633
Streptomyces coelicolor	LOTUS Database	35616633
Streptomyces griseus	LOTUS Database	35616633
Streptomyces hebeiensis	LOTUS Database	35616633
Streptomyces lydicus	LOTUS Database	35616633
Streptomyces malaysiense	LOTUS Database	35616633
Streptomyces mirabilis	LOTUS Database	35616633
Streptomyces parvulus	LOTUS Database	35616633
Streptomyces pilosus	LOTUS Database	35616633
Streptomyces wadayamensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetohydroxamic acids. These are organic compounds that contain a hydroxamic acid group carrying a methyl group attached to its carbon center.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Acetohydroxamic acids

Alternative Parents

Substituents

Acetamide
Acetohydroxamic acid
Amino acid or derivatives
Carboximidic acid
Carboximidic acid derivative
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carbonyl group
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acyclic desferrioxamine (CHEBI:4356 )
a hydroxamate siderophore (CPD-3764 )

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	0.93	ALOGPS
logP	-3.4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.92	ChemAxon
pKa (Strongest Basic)	10.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	205.84 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	144.95 m³·mol⁻¹	ChemAxon
Polarizability	62.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014884

DrugBank ID

DB00746

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2867

KEGG Compound ID

C06940

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Deferoxamine

METLIN ID

Not Available

PubChem Compound

2973

PDB ID

Not Available

ChEBI ID

4356

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid (NP0324755)

MOL for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)

3D MOL for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)

3D SDF for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)

3D-SDF for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)

PDB for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)

3D PDB for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)

SMILES for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)

INCHI for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)

Structure for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)

3D Structure for NP0324755 (3-[(5-aminopentyl)(hydroxy)carbamoyl]-n-[5-(n-hydroxy-3-{[5-(n-hydroxyacetamido)pentyl]-c-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid)