NP-MRD: Showing NP-Card for 4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid (NP0267341)

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Record Information

Version

1.0

Created at

2022-09-08 12:05:59 UTC

Updated at

2022-09-08 12:05:59 UTC

NP-MRD ID

NP0267341

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid

Description

Staphyloferrin B belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Staphyloferrin B is a very strong basic compound (based on its pKa). 4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid is found in Cupriavidus necator. It was first documented in 2004 (PMID: 15547261). A siderophore composed from L-2,3-diaminopropionic acid, citric acid, 1,2-diaminoethane and alpha-ketoglutaric acid units (PMID: 19775248) (PMID: 20810662) (PMID: 21402762) (PMID: 21906287).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041411032D          

 32 31  0  0  1  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052   -2.4454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302   -2.4454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052   -1.0164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802   -2.4454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 16  5  1  0  0  0  0
 16  6  1  0  0  0  0
 16 15  1  6  0  0  0
  8 17  1  6  0  0  0
 18  3  1  4  0  0  0
 18 10  2  0  0  0  0
 19  4  1  4  0  0  0
 19 11  2  0  0  0  0
 20  7  1  4  0  0  0
 20 12  2  0  0  0  0
 21  9  2  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 13  2  0  0  0  0
 26 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28 14  2  0  0  0  0
 29 15  2  0  0  0  0
 30 15  1  0  0  0  0
 16 31  1  1  0  0  0
  8 32  1  6  0  0  0
M  END

     RDKit          3D

 55 54  0  0  0  0  0  0  0  0999 V2000
   -7.7519    2.4041    0.3061 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7299    1.4712   -0.1311 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4369    1.7697    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974    0.8822    0.1872 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8615    0.7989   -0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3302    1.6534   -1.9577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7824   -0.1442   -1.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3502   -0.9851   -0.1405 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4729   -1.7206    0.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3307   -2.0314   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0939   -1.5067   -1.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147   -0.7675   -2.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -1.7203   -0.4987 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -1.2493   -0.9715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3561   -1.5145    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6373   -1.0515   -0.3825 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375    0.1929   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0286    1.0678    0.2510 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2790    0.6590   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0666    1.2841    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2929    0.3305    1.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378   -0.0165    2.2087 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6060   -0.2364    1.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5668    0.1104    1.0014 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8192   -1.1258    2.7723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8168   -0.2107    0.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8126    0.5347    0.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3783   -0.2462    2.2590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2221    0.1074    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3470   -0.0994    0.5520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4077   -0.9837   -0.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7297    2.4608    1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6706    2.0087    0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5430    1.6792   -1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5618    1.7564    1.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1489    2.8086    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6610    2.1754   -2.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9271    0.4201   -1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251   -0.8300   -2.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1972   -2.5861    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0848   -2.5692    0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -2.8028   -1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6299   -0.0379   -2.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2446   -0.1663   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317   -1.7920   -1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635   -2.5880    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0451   -0.9558    0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0985    2.0816    0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1879    1.3793   -1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8668   -0.1980   -1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4805    2.1616    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0434    1.5936   -0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4195   -2.0589    2.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9400   -0.7158    3.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2273   -1.7019    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 25  1  0
 23 24  2  0
  8 26  1  0
 26 28  1  0
 26 27  2  0
  2 29  1  0
 29 31  1  0
 29 30  2  0
  2 34  1  6
  1 32  1  0
  1 33  1  0
  3 35  1  0
  3 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 12 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 25 53  1  0
 28 54  1  0
 31 55  1  0
M  END


  Mrv0541 05041411032D          

 32 31  0  0  1  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052   -2.4454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302   -2.4454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052   -1.0164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802   -2.4454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 16  5  1  0  0  0  0
 16  6  1  0  0  0  0
 16 15  1  6  0  0  0
  8 17  1  6  0  0  0
 18  3  1  4  0  0  0
 18 10  2  0  0  0  0
 19  4  1  4  0  0  0
 19 11  2  0  0  0  0
 20  7  1  4  0  0  0
 20 12  2  0  0  0  0
 21  9  2  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 25 13  2  0  0  0  0
 26 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28 14  2  0  0  0  0
 29 15  2  0  0  0  0
 30 15  1  0  0  0  0
 16 31  1  1  0  0  0
  8 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0267341

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](N)(CN=C(O)C[C@@](O)(CC(O)=NCCN=C(O)CCC(=O)C(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N4O11/c17-8(13(25)26)7-20-12(24)6-16(31,15(29)30)5-11(23)19-4-3-18-10(22)2-1-9(21)14(27)28/h8,31H,1-7,17H2,(H,18,22)(H,19,23)(H,20,24)(H,25,26)(H,27,28)(H,29,30)/t8-,16-/m0/s1

> <INCHI_KEY>
SIAZVTIHOHTZDD-PWJLMRLQSA-N

> <FORMULA>
C16H24N4O11

> <MOLECULAR_WEIGHT>
448.382

> <EXACT_MASS>
448.14415763

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
41.508431874193946

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2-{[(3S)-3-({[(2S)-2-amino-2-carboxyethyl]-C-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-C-hydroxycarbonimidoyl]-2-oxobutanoic acid

> <ALOGPS_LOGP>
-2.37

> <JCHEM_LOGP>
-5.419077270362425

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.7446371996945307

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4930103627762028

> <JCHEM_PKA_STRONGEST_BASIC>
9.16143030910567

> <JCHEM_POLAR_SURFACE_AREA>
272.98999999999995

> <JCHEM_REFRACTIVITY>
98.0394

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2-{[(3S)-3-({[(2S)-2-amino-2-carboxyethyl]-C-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-C-hydroxycarbonimidoyl]-2-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+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+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
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+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    9                                                       
CONECT    2    1   10                                                       
CONECT    3    4   18                                                       
CONECT    4    3   19                                                       
CONECT    5   11   16                                                       
CONECT    6   12   16                                                       
CONECT    7    8   20                                                       
CONECT    8    7   13   17   32                                             
CONECT    9    1   14   21                                                  
CONECT   10    2   18   22                                                  
CONECT   11    5   19   23                                                  
CONECT   12    6   20   24                                                  
CONECT   13    8   25   26                                                  
CONECT   14    9   27   28                                                  
CONECT   15   16   29   30                                                  
CONECT   16    5    6   15   31                                             
CONECT   17    8                                                            
CONECT   18    3   10                                                       
CONECT   19    4   11                                                       
CONECT   20    7   12                                                       
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32    8                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₄N₄O₁₁

Average Mass

448.3820 Da

Monoisotopic Mass

448.14416 Da

IUPAC Name

4-[(2-{[(3S)-3-({[(2S)-2-amino-2-carboxyethyl]-C-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-C-hydroxycarbonimidoyl]-2-oxobutanoic acid

Traditional Name

4-[(2-{[(3S)-3-({[(2S)-2-amino-2-carboxyethyl]-C-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-C-hydroxycarbonimidoyl]-2-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CN=C(O)C[C@@](O)(CC(O)=NCCN=C(O)CCC(=O)C(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C16H24N4O11/c17-8(13(25)26)7-20-12(24)6-16(31,15(29)30)5-11(23)19-4-3-18-10(22)2-1-9(21)14(27)28/h8,31H,1-7,17H2,(H,18,22)(H,19,23)(H,20,24)(H,25,26)(H,27,28)(H,29,30)/t8-,16-/m0/s1

InChI Key

SIAZVTIHOHTZDD-PWJLMRLQSA-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
Cupriavidus necator	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Tricarboxylic acid or derivatives
Alpha-hydroxy acid
Alpha-keto acid
Fatty amide
Hydroxy acid
Keto acid
N-acyl-amine
Fatty acyl
Tertiary alcohol
Alpha-hydroxy ketone
Secondary carboxylic acid amide
Amino acid
Carboxamide group
Ketone
Carboxylic acid
Organic oxide
Primary aliphatic amine
Alcohol
Amine
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-2.4	ALOGPS
logP	-5.4	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	272.99 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	98.04 m³·mol⁻¹	ChemAxon
Polarizability	41.51 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-12590

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46861568

PDB ID

Not Available

ChEBI ID

134612

Good Scents ID

Not Available

References

General References

Bhatt G, Denny TP: Ralstonia solanacearum iron scavenging by the siderophore staphyloferrin B is controlled by PhcA, the global virulence regulator. J Bacteriol. 2004 Dec;186(23):7896-904. doi: 10.1128/JB.186.23.7896-7904.2004. [PubMed:15547261 ]
Cheung J, Beasley FC, Liu S, Lajoie GA, Heinrichs DE: Molecular characterization of staphyloferrin B biosynthesis in Staphylococcus aureus. Mol Microbiol. 2009 Nov;74(3):594-608. doi: 10.1111/j.1365-2958.2009.06880.x. Epub 2009 Sep 22. [PubMed:19775248 ]
Grigg JC, Cheung J, Heinrichs DE, Murphy ME: Specificity of Staphyloferrin B recognition by the SirA receptor from Staphylococcus aureus. J Biol Chem. 2010 Nov 5;285(45):34579-88. doi: 10.1074/jbc.M110.172924. Epub 2010 Sep 1. [PubMed:20810662 ]
Beasley FC, Marolda CL, Cheung J, Buac S, Heinrichs DE: Staphylococcus aureus transporters Hts, Sir, and Sst capture iron liberated from human transferrin by Staphyloferrin A, Staphyloferrin B, and catecholamine stress hormones, respectively, and contribute to virulence. Infect Immun. 2011 Jun;79(6):2345-55. doi: 10.1128/IAI.00117-11. Epub 2011 Mar 14. [PubMed:21402762 ]
Beasley FC, Cheung J, Heinrichs DE: Mutation of L-2,3-diaminopropionic acid synthase genes blocks staphyloferrin B synthesis in Staphylococcus aureus. BMC Microbiol. 2011 Sep 9;11:199. doi: 10.1186/1471-2180-11-199. [PubMed:21906287 ]
LOTUS database [Link]

Showing NP-Card for 4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid (NP0267341)

MOL for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)

3D MOL for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)

3D SDF for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)

3D-SDF for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)

PDB for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)

3D PDB for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)

SMILES for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)

INCHI for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)

Structure for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)

3D Structure for NP0267341 (4-[(2-{[(3s)-3-({[(2s)-2-amino-2-carboxyethyl]-c-hydroxycarbonimidoyl}methyl)-3-carboxy-1,3-dihydroxypropylidene]amino}ethyl)-c-hydroxycarbonimidoyl]-2-oxobutanoic acid)