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COCONUT Compound

Melatonin

CNP0139257.0 · C13H16N2O2 · View on COCONUT ↗

2D Structure

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Identifiers

NameMelatonin
IUPAC Name~{N}-[2-(5-methoxy-1~{H}-indol-3-yl)ethyl]acetamide
COCONUT IDCNP0139257.0
CAS73-31-4, 8041-44-9
InChIKeyDRLFMBDRBRZALE-UHFFFAOYSA-N
InChIInChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
SMILESCOC1=CC=C2NC=C(CCNC(C)=O)C2=C1

Properties

Molecular FormulaC13H16N2O2
Molecular Weight232.28
Exact Mass232.12118
Log P (ALogP)1.86
TPSA54.12
H-Bond Donors / Acceptors2 / 2
Rotatable Bonds4
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.84
NP-likeness-0.52

Classification

NP PathwayAlkaloids
NP SuperclassTryptophan alkaloids
NP ClassSimple indole alkaloids
Chemical SuperclassOrganoheterocyclic compounds
Chemical ClassIndoles and derivatives
Chemical SubclassIndoles

Reported in GR-MAPs Plants

Andrographis paniculata as “Andrographis paniculata” in COCONUT
Nicotiana tabacum as “Nicotiana tabacum” in COCONUT
Artemisia annua as “Artemisia annua” in COCONUT

References (22)

  1. 10.1002/(SICI)1097-0185(199605)245:1<13::AID-AR3>3.0.CO;2-G
  2. 10.1002/1099-0801(200008)14:5<306::AID-BMC986>3.0.CO;2-7
  3. 10.1007/S00114-002-0376-1
  4. 10.1007/S11306-012-0464-Y
  5. 10.1007/S11306-016-1051-4
  6. 10.1016/0014-5793(70)80091-6
  7. 10.1016/J.PHYTOCHEM.2007.05.016
  8. 10.1016/S0024-3205(03)00252-2
  9. 10.1016/S0031-9422(01)00273-4
  10. 10.1016/S0031-9422(96)00568-7
  11. 10.1016/S0140-6736(05)64014-7
  12. 10.1021/JF010321+
  13. 10.1021/JO040272A
  14. 10.1021/NP030475E
  15. 10.1034/J.1600-079X.2001.310102.X
  16. 10.1038/NBT.2488
  17. 10.1038/nbt.2488
  18. 10.1093/pcp/pcn183
  19. 10.1111/J.1600-079X.1995.TB00136.X
  20. 10.1515/ZNC-1998-9-1025
  21. 10.3389/FMOLB.2018.00096
  22. 10.3390/NU9040367

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.