NP-MRD: Showing NP-Card for Nicotianamine (NP0023388)

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Record Information

Version

2.0

Created at

2021-01-06 08:28:24 UTC

Updated at

2021-07-15 17:41:37 UTC

NP-MRD ID

NP0023388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nicotianamine

Provided By

NPAtlas

Description

Nicotianamine is found in Angelica keiskei, Avena sativa, Corchorus olitorius, Medicago sativa, Nicotiana megalosiphon, Nicotiana tabacum and Streptomyces. Nicotianamine was first documented in 1996 (PMID: 9031677). Based on a literature review a small amount of articles have been published on Nicotianamine (PMID: 16245165) (PMID: 18823453) (PMID: 34488609) (PMID: 34411783).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105413D          

 42 42  0  0  0  0            999 V2000
   -5.3368   -2.5034   -0.2815 N   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3303   -1.5995    0.3091 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2346   -1.4620   -0.7448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1332   -0.5600   -0.2779 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1196   -0.4209   -1.3151 N   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1349    0.5514   -0.8343 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2685   -0.0898   -0.8845 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2445    0.9002   -0.4092 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6280    0.5737   -0.3744 N   0  0  1  0  0  0  0  0  0  0  0  0
    4.3059    1.8269    0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2406    1.2474    1.4879 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2400   -0.0259    0.7458 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7078   -1.2466    1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028   -1.3841    2.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4034   -2.3336    0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    1.8054   -1.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571    1.8155   -2.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4006    2.9918   -1.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939   -0.3185    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1748   -0.1624    0.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3816    0.7087    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2187   -2.3837    0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9929   -3.4868   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9715   -2.0950    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8341   -2.4637   -0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -1.0865   -1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    0.4223    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339   -1.0690    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5776   -1.3369   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.7664    0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444   -1.0672   -0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4110   -0.3281   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814    1.7873   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636    1.3461    0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3611    1.8875   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072    2.7234   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798    1.5615    2.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1753    1.4891    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3353   -0.2303    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5931   -2.2520   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.8231   -0.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    1.6777    0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 12  9  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  1  0  0  0
  3 25  1  0  0  0  0
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  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  1  0  0  0
  7 31  1  0  0  0  0
  7 32  1  0  0  0  0
  8 33  1  0  0  0  0
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 10 36  1  0  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
 12 39  1  6  0  0  0
 15 40  1  0  0  0  0
 18 41  1  0  0  0  0
 21 42  1  0  0  0  0
M  END

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
   -5.3368   -2.5034   -0.2815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3303   -1.5995    0.3091 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2346   -1.4620   -0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -0.5600   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1196   -0.4209   -1.3151 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1349    0.5514   -0.8343 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2685   -0.0898   -0.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    0.9002   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280    0.5737   -0.3744 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059    1.8269    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    1.2474    1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2400   -0.0259    0.7458 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7078   -1.2466    1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028   -1.3841    2.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4034   -2.3336    0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    1.8054   -1.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571    1.8155   -2.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4006    2.9918   -1.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939   -0.3185    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1748   -0.1624    0.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3816    0.7087    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2187   -2.3837    0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9929   -3.4868   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9715   -2.0950    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8341   -2.4637   -0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -1.0865   -1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    0.4223    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339   -1.0690    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5776   -1.3369   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.7664    0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444   -1.0672   -0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4110   -0.3281   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814    1.7873   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636    1.3461    0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3611    1.8875   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072    2.7234   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798    1.5615    2.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1753    1.4891    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3353   -0.2303    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5931   -2.2520   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.8231   -0.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    1.6777    0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 12  9  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  6
 15 40  1  0
 18 41  1  0
 21 42  1  0
M  END


  Mrv1652306242105413D          

 42 42  0  0  0  0            999 V2000
   -5.3368   -2.5034   -0.2815 N   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3303   -1.5995    0.3091 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2346   -1.4620   -0.7448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1332   -0.5600   -0.2779 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1196   -0.4209   -1.3151 N   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1349    0.5514   -0.8343 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2685   -0.0898   -0.8845 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2445    0.9002   -0.4092 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6280    0.5737   -0.3744 N   0  0  1  0  0  0  0  0  0  0  0  0
    4.3059    1.8269    0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2406    1.2474    1.4879 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2400   -0.0259    0.7458 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7078   -1.2466    1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028   -1.3841    2.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4034   -2.3336    0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    1.8054   -1.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571    1.8155   -2.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4006    2.9918   -1.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939   -0.3185    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1748   -0.1624    0.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3816    0.7087    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2187   -2.3837    0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9929   -3.4868   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9715   -2.0950    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8341   -2.4637   -0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -1.0865   -1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    0.4223    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339   -1.0690    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5776   -1.3369   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.7664    0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444   -1.0672   -0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4110   -0.3281   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814    1.7873   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636    1.3461    0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3611    1.8875   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072    2.7234   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798    1.5615    2.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1753    1.4891    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3353   -0.2303    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5931   -2.2520   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.8231   -0.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    1.6777    0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 12  9  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  1  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  1  0  0  0
  7 31  1  0  0  0  0
  7 32  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
 12 39  1  6  0  0  0
 15 40  1  0  0  0  0
 18 41  1  0  0  0  0
 21 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])N([H])[C@]([H])(C(=O)O[H])C([H])([H])C([H])([H])N1C([H])([H])C([H])([H])[C@@]1([H])C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H21N3O6/c13-7(10(16)17)1-4-14-8(11(18)19)2-5-15-6-3-9(15)12(20)21/h7-9,14H,1-6,13H2,(H,16,17)(H,18,19)(H,20,21)/t7-,8-,9-/m0/s1

> <INCHI_KEY>
KRGPXXHMOXVMMM-CIUDSAMLSA-N

> <FORMULA>
C12H21N3O6

> <MOLECULAR_WEIGHT>
303.3116

> <EXACT_MASS>
303.143035419

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.64479194752961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(3S)-3-{[(3S)-3-amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid

> <ALOGPS_LOGP>
-3.08

> <JCHEM_LOGP>
-9.265535685889175

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
1.6418677603594558

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0490559229707346

> <JCHEM_PKA_STRONGEST_BASIC>
10.274833427540301

> <JCHEM_POLAR_SURFACE_AREA>
153.19

> <JCHEM_REFRACTIVITY>
70.7792

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S,S,S)-nicotianamine

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
   -5.3368   -2.5034   -0.2815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3303   -1.5995    0.3091 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2346   -1.4620   -0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -0.5600   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1196   -0.4209   -1.3151 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1349    0.5514   -0.8343 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2685   -0.0898   -0.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    0.9002   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280    0.5737   -0.3744 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059    1.8269    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    1.2474    1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2400   -0.0259    0.7458 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7078   -1.2466    1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028   -1.3841    2.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4034   -2.3336    0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    1.8054   -1.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571    1.8155   -2.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4006    2.9918   -1.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939   -0.3185    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1748   -0.1624    0.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3816    0.7087    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2187   -2.3837    0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9929   -3.4868   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9715   -2.0950    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8341   -2.4637   -0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -1.0865   -1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    0.4223    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339   -1.0690    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5776   -1.3369   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.7664    0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444   -1.0672   -0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4110   -0.3281   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814    1.7873   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636    1.3461    0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3611    1.8875   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072    2.7234   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798    1.5615    2.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1753    1.4891    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3353   -0.2303    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5931   -2.2520   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.8231   -0.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    1.6777    0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 12  9  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  6
 15 40  1  0
 18 41  1  0
 21 42  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -5.337  -2.503  -0.282  0.00  0.00           N+0
HETATM    2  C   UNK     0      -4.330  -1.599   0.309  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.235  -1.462  -0.745  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.133  -0.560  -0.278  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.120  -0.421  -1.315  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.135   0.551  -0.834  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.268  -0.090  -0.885  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.244   0.900  -0.409  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.628   0.574  -0.374  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.306   1.827   0.067  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.241   1.247   1.488  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.240  -0.026   0.746  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.708  -1.247   1.309  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.503  -1.384   2.566  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.403  -2.334   0.490  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.240   1.805  -1.573  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.057   1.815  -2.575  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.401   2.992  -1.358  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.994  -0.319   0.591  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.175  -0.162   0.192  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.382   0.709   1.269  0.00  0.00           O+0
HETATM   22  H   UNK     0      -6.219  -2.384   0.222  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.993  -3.487  -0.108  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.971  -2.095   1.228  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.834  -2.464  -0.927  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.726  -1.087  -1.669  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.470   0.422   0.068  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.634  -1.069   0.587  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.578  -1.337  -1.404  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.403   0.766   0.219  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.244  -1.067  -0.391  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.411  -0.328  -1.991  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.181   1.787  -1.111  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.964   1.346   0.596  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.361   1.888  -0.244  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.707   2.723  -0.090  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.380   1.562   2.065  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.175   1.489   2.059  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.335  -0.230   0.436  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.593  -2.252  -0.521  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.003   3.823  -0.930  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.332   1.678   0.957  0.00  0.00           H+0
CONECT    1    2   22   23                                                  
CONECT    2    1    3   19   24                                             
CONECT    3    2    4   25   26                                             
CONECT    4    3    5   27   28                                             
CONECT    5    4    6   29                                                  
CONECT    6    5    7   16   30                                             
CONECT    7    6    8   31   32                                             
CONECT    8    7    9   33   34                                             
CONECT    9    8   10   12                                                  
CONECT   10    9   11   35   36                                             
CONECT   11   10   12   37   38                                             
CONECT   12   11   13    9   39                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   40                                                       
CONECT   16    6   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   41                                                       
CONECT   19    2   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   42                                                       
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    2                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   15                                                            
CONECT   41   18                                                            
CONECT   42   21                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   84    0
END

RDKit          3D

42 42  0  0  0  0  0  0  0  0999 V2000
   -5.3368   -2.5034   -0.2815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3303   -1.5995    0.3091 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2346   -1.4620   -0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -0.5600   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1196   -0.4209   -1.3151 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1349    0.5514   -0.8343 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2685   -0.0898   -0.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    0.9002   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280    0.5737   -0.3744 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059    1.8269    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    1.2474    1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2400   -0.0259    0.7458 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7078   -1.2466    1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028   -1.3841    2.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4034   -2.3336    0.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    1.8054   -1.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571    1.8155   -2.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4006    2.9918   -1.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9939   -0.3185    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1748   -0.1624    0.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3816    0.7087    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2187   -2.3837    0.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9929   -3.4868   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9715   -2.0950    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8341   -2.4637   -0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -1.0865   -1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    0.4223    0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339   -1.0690    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5776   -1.3369   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.7664    0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2444   -1.0672   -0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4110   -0.3281   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1814    1.7873   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636    1.3461    0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3611    1.8875   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072    2.7234   -0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3798    1.5615    2.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1753    1.4891    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3353   -0.2303    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5931   -2.2520   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.8231   -0.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    1.6777    0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 12  9  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  6
 15 40  1  0
 18 41  1  0
 21 42  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
N-(N-(3-Amino-3-carboxypropyl)-3-amino-3-carboxypropyl)azetidine-2-carboxylic acid	MeSH

Chemical Formula

C₁₂H₂₁N₃O₆

Average Mass

303.3116 Da

Monoisotopic Mass

303.14304 Da

IUPAC Name

(2S)-1-[(3S)-3-{[(3S)-3-amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid

Traditional Name

(S,S,S)-nicotianamine

CAS Registry Number

Not Available

SMILES

N[C@@H](CCN[C@@H](CCN1CC[C@H]1C(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C12H21N3O6/c13-7(10(16)17)1-4-14-8(11(18)19)2-5-15-6-3-9(15)12(20)21/h7-9,14H,1-6,13H2,(H,16,17)(H,18,19)(H,20,21)/t7-,8-,9-/m0/s1

InChI Key

KRGPXXHMOXVMMM-CIUDSAMLSA-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
Angelica keiskei	LOTUS Database	35616633
Avena sativa	LOTUS Database	35616633
Avena sativa L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Corchorus olitorius	LOTUS Database	35616633
Fagopyrum esculentum	KNApSAcK Database	22123792
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Medicago sativa	LOTUS Database	35616633
Nicotiana megalosiphon	LOTUS Database	35616633
Nicotiana tabacum	LOTUS Database	35616633
Nicotiana tabacum L.	KNApSAcK Database	22123792
Oryza sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Streptomyces	NPAtlas	9031677
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Species Where Detected

Species Name	Source	Reference
Streptomyces sp. SANK 62595	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound 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
Amino fatty acid
Azetidinecarboxylic acid
Fatty acyl
Azetidine
Tertiary amine
Tertiary aliphatic amine
Amino acid
Organoheterocyclic compound
Azacycle
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

nicotianamine (CHEBI:17721 )

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	-3.1	ALOGPS
logP	-9.3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.05	ChemAxon
pKa (Strongest Basic)	10.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.19 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	70.78 m³·mol⁻¹	ChemAxon
Polarizability	29.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020584

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Nicotianamine

METLIN ID

Not Available

PubChem Compound

9882882

PDB ID

Not Available

ChEBI ID

17721

Good Scents ID

Not Available

References

General References

Suzuki K, Shimada K, Nozoe S, Tanzawa K, Ogita T: Isolation of nicotianamine as a gelatinase inhibitor. J Antibiot (Tokyo). 1996 Dec;49(12):1284-5. doi: 10.7164/antibiotics.49.1284. [PubMed:9031677 ]
Pianelli K, Mari S, Marques L, Lebrun M, Czernic P: Nicotianamine over-accumulation confers resistance to nickel in Arabidopsis thaliana. Transgenic Res. 2005 Oct;14(5):739-48. doi: 10.1007/s11248-005-7159-3. [PubMed:16245165 ]
Usuda K, Wada Y, Ishimaru Y, Kobayashi T, Takahashi M, Nakanishi H, Nagato Y, Mori S, Nishizawa NK: Genetically engineered rice containing larger amounts of nicotianamine to enhance the antihypertensive effect. Plant Biotechnol J. 2009 Jan;7(1):87-95. doi: 10.1111/j.1467-7652.2008.00374.x. Epub 2008 Sep 24. [PubMed:18823453 ]
Farshi P, Kaya EC, Hashempour-Baltork F, Khosravi-Darani K: The effect of plant metabolites on coronaviruses: A comprehensive review focusing on their IC50 values and molecular docking scores. Mini Rev Med Chem. 2021 Aug 31. pii: MRMC-EPUB-117575. doi: 10.2174/1389557521666210831152511. [PubMed:34488609 ]
Bari MA, El-Shehawi AM, Elseehy MM, Naheen NN, Rahman MM, Kabir AH: Molecular characterization and bioinformatics analysis of transporter genes associated with Cd-induced phytotoxicity in rice (Oryza sativa L.). Plant Physiol Biochem. 2021 Oct;167:438-448. doi: 10.1016/j.plaphy.2021.08.024. Epub 2021 Aug 15. [PubMed:34411783 ]

Showing NP-Card for Nicotianamine (NP0023388)

MOL for NP0023388 (Nicotianamine)

3D MOL for NP0023388 (Nicotianamine)

3D SDF for NP0023388 (Nicotianamine)

3D-SDF for NP0023388 (Nicotianamine)

PDB for NP0023388 (Nicotianamine)

3D PDB for NP0023388 (Nicotianamine)

SMILES for NP0023388 (Nicotianamine)

INCHI for NP0023388 (Nicotianamine)

Structure for NP0023388 (Nicotianamine)

3D Structure for NP0023388 (Nicotianamine)