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COCONUT Compound

Nicotianamine

CNP0178593.1 · C12H21N3O6 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

NameNicotianamine
IUPAC Name(2~{S})-1-[(3~{S})-3-[[(3~{S})-3-amino-3-carboxy-propyl]amino]-3-carboxy-propyl]azetidine-2-carboxylic acid
COCONUT IDCNP0178593.1
CAS34441-14-0
InChIKeyKRGPXXHMOXVMMM-CIUDSAMLSA-N
InChIInChI=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
SMILESN[C@@H](CCN[C@@H](CCN1CC[C@H]1C(=O)O)C(=O)O)C(=O)O

Properties

Molecular FormulaC12H21N3O6
Molecular Weight303.31
Exact Mass303.14304
Log P (ALogP)-1.62
TPSA153.19
H-Bond Donors / Acceptors5 / 6
Rotatable Bonds10
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.32
NP-likeness0.33

Classification

NP PathwayAmino acids and Peptides
NP SuperclassSmall peptides
NP ClassAminoacids
Chemical SuperclassOrganic acids and derivatives
Chemical ClassCarboxylic acids and derivatives
Chemical SubclassAmino acids, peptides, and analogues

Reported in GR-MAPs Plants

Nicotiana tabacum as “Nicotiana Tabacum; Nicotiana tabacum L.” in COCONUT
Arabidopsis thaliana as “Arabidopsis thaliana” in COCONUT

References (10)

  1. 10.1007/BF01142552
  2. 10.1016/0031-9422(82)83012-4
  3. 10.1016/J.PHYTOCHEM.2005.12.022
  4. 10.1016/S0031-9422(00)91014-8
  5. 10.1111/PCE.12842
  6. 10.1271/BBB.57.1107
  7. 10.3136/FSTI9596T9798.4.223
  8. 10.3177/JNSV.45.375
  9. 10.7164/ANTIBIOTICS.49.1284
  10. 10.7164/antibiotics.49.1284

Data from COCONUT (COlleCtion of Open Natural prodUcTs), released under CC0. Chandrasekhar V. et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Research (2024), doi:10.1093/nar/gkae1063. COCONUT release 2026-10.