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COCONUT Compound

VOLVALTRATE B

CNP0288909.1 · C27H41ClO11 · View on COCONUT ↗

2D Structure

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Identifiers

NameVOLVALTRATE B
IUPAC Name[(1~{S},4~{a}~{R},6~{S},7~{S},7~{a}~{S})-6-acetoxy-7-(chloromethyl)-4~{a},7-dihydroxy-1-(3-methylbutanoyloxy)-1,5,6,7~{a}-tetrahydrocyclopenta[c]pyran-4-yl]methyl (2~{R})-3-methyl-2-(3-methylbutanoyloxy)butanoate
COCONUT IDCNP0288909.1
InChIKeyOEVPPNBQSYOUCV-PXKJKYEHSA-N
InChIInChI=1S/C27H41ClO11/c1-14(2)8-20(30)38-22(16(5)6)24(32)35-11-18-12-36-25(39-21(31)9-15(3)4)23-26(18,33)10-19(37-17(7)29)27(23,34)13-28/h12,14-16,19,22-23,25,33-34H,8-11,13H2,1-7H3/t19-,22+,23-,25-,26-,27+/m0/s1
SMILESCC(=O)O[C@H]1C[C@]2(O)C(COC(=O)[C@H](OC(=O)CC(C)C)C(C)C)=CO[C@@H](OC(=O)CC(C)C)[C@@H]2[C@@]1(O)CCl

Properties

Molecular FormulaC27H41ClO11
Molecular Weight577.07
Exact Mass576.23374
Log P (ALogP)2.63
TPSA154.89
H-Bond Donors / Acceptors2 / 11
Rotatable Bonds12
Lipinski's Rule of 5 Violations2
QED Drug-likeness0.20
NP-likeness2.21

Classification

NP PathwayTerpenoids
NP SuperclassMonoterpenoids
NP ClassIridoids monoterpenoids
Chemical SuperclassOrganic acids and derivatives
Chemical ClassCarboxylic acids and derivatives
Chemical SubclassTetracarboxylic acids and derivatives

Reported in GR-MAPs Plants

Valeriana jatamansi as “Valeriana jatamansi” in COCONUT

References (4)

  1. 10.1016/J.PHYTOCHEM.2012.08.015
  2. 10.1021/NP100426J
  3. 10.1021/NP9003382
  4. 10.1021/np100426j

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.