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COCONUT Compound

Longispinogenin

CNP0218101.4 · C30H50O3 · View on COCONUT ↗

2D Structure

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Identifiers

NameLongispinogenin
IUPAC Name(3~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{S},8~{a}~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-8~{a}-(hydroxymethyl)-4,4,6~{a},6~{b},11,11,14~{b}-heptamethyl-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicene-3,8-diol
COCONUT IDCNP0218101.4
CAS465-94-1
InChIKeyYHGVYECWZWIVJC-MZGFOBBZSA-N
InChIInChI=1S/C30H50O3/c1-25(2)14-15-30(18-31)20(16-25)19-8-9-22-27(5)12-11-23(32)26(3,4)21(27)10-13-28(22,6)29(19,7)17-24(30)33/h8,20-24,31-33H,9-18H2,1-7H3/t20-,21-,22+,23-,24-,27-,28+,29+,30+/m0/s1
SMILESCC1(C)CC[C@]2(CO)[C@@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Properties

Molecular FormulaC30H50O3
Molecular Weight458.73
Exact Mass458.37600
Log P (ALogP)6.11
TPSA60.69
H-Bond Donors / Acceptors3 / 3
Rotatable Bonds1
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.42
NP-likeness3.35

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP ClassOleanane triterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTriterpenoids

Reported in GR-MAPs Plants

Gymnema sylvester as “Gymnema sylvestre” in COCONUT

References (8)

  1. 10.1016/0031-9422(85)80062-5
  2. 10.1016/S0021-9673(01)81975-0
  3. 10.1016/S0031-9422(00)84536-7
  4. 10.1016/S0031-9422(97)00005-8
  5. 10.1016/S0305-1978(01)00060-6
  6. 10.1021/JF010164E
  7. 10.1021/NP50028A021
  8. 10.1071/CH9750165

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.