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COCONUT Compound

Chebulinic acid

CNP0157329.4 · C41H32O27 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

NameChebulinic acid
IUPAC Name2-[(4~{R},5~{S},7~{R},8~{R},11~{S},12~{S},13~{S},21~{S})-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-[(3,4,5-trihydroxybenzoyl)oxymethyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(19),16(20),17-trien-11-yl]acetic acid
COCONUT IDCNP0157329.4
CAS18942-26-2
InChIKeyYGVHOSGNOYKRIH-FJPMMHPYSA-N
InChIInChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30-,31+,33-,34+,41-/m0/s1
SMILESO=C(O)C[C@@H]1C(=O)O[C@H]2[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@@H](OC(=O)C3=CC(O)=C(O)C4=C3[C@H]1[C@H](O)C(=O)O4)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)O[C@@H]2COC(=O)C1=CC(O)=C(O)C(O)=C1

Properties

Molecular FormulaC41H32O27
Molecular Weight956.68
Exact Mass956.11310
Log P (ALogP)0.02
TPSA447.09
H-Bond Donors / Acceptors13 / 26
Rotatable Bonds9
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.05
NP-likeness1.30

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassPhenolic acids (C6-C1)
NP ClassGallotannins
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassTannins
Chemical SubclassHydrolyzable tannins

Reported in GR-MAPs Plants

Terminalia chebula as “Terminalia Chebula” in COCONUT
Emblica officinalis as “Phyllanthus Emblica” in COCONUT

References (3)

  1. 10.1002/jssc.201501358
  2. 10.1016/j.phytochem.2010.03.018
  3. 10.1021/np50094a030

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.