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COCONUT Compound

NADPH

CNP0265401.2 · C21H30N7O17P3 · View on COCONUT ↗

2D Structure

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Identifiers

NameNADPH
IUPAC Name[[(2~{S},3~{R},4~{R},5~{S})-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] [(2~{S},3~{S},4~{R},5~{S})-5-(3-carbamoyl-4~{H}-pyridin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl hydrogen phosphate
COCONUT IDCNP0265401.2
InChIKeyACFIXJIJDZMPPO-VOLSVOPZSA-N
InChIInChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13+,14+,15+,16+,20-,21-/m0/s1
SMILESNC(=O)C1=CN([C@H]2O[C@@H](CO[P@](=O)(O)O[P@@](=O)(O)OC[C@@H]3O[C@H](N4C=NC5=C(N)N=CN=C54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1

Properties

Molecular FormulaC21H30N7O17P3
Molecular Weight745.43
Exact Mass745.09110
Log P (ALogP)-2.57
TPSA364.15
H-Bond Donors / Acceptors9 / 19
Rotatable Bonds13
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.10
NP-likeness0.98

Classification

NP PathwayCarbohydrates
NP SuperclassNucleosides
NP ClassPurine nucleos(t)ides
Chemical SuperclassNucleosides, nucleotides, and analogues
Chemical ClassPurine nucleotides
Chemical SubclassPurine ribonucleotides

Reported in GR-MAPs Plants

Nicotiana tabacum as “Nicotiana tabacum” in COCONUT
Arabidopsis thaliana as “Arabidopsis thaliana” in COCONUT
Oryza sativa as “Oryza sativa” in COCONUT

References (9)

  1. 10.1006/ABBI.2001.2483
  2. 10.1016/0031-9422(88)87028-6
  3. 10.1016/J.JMB.2009.07.023
  4. 10.1046/J.1432-1033.2002.03172.X
  5. 10.1104/PP.103.037192
  6. 10.1105/TPC.17.00766
  7. 10.1111/J.1365-313X.2004.02187.X
  8. 10.1111/J.1742-4658.2006.05446.X
  9. 10.1111/NPH.14412

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.