Ecabet
Basic information
- CAS
33159-27-2- Standard SMILES
CC(C)c1cc2c(cc1S(=O)(=O)O)[C@@]1(C)CCC[C@@](C)(C(=O)O)[C@@H]1CC2- InChIKey
IWCWQNVIUXZOMJ-MISYRCLQSA-N- Molecular formula
- C20H28O5S
- Average molar mass
- 380.5 g/mol
- Monoisotopic mass
- 380.16574516
Overview
Ecabet is a diterpenoid.
Names & identifiers
- Preferred name
- Ecabet
- IUPAC
- (1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-6-sulfo-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid
- English name
- Ecabet
- Molecular formula
- C20H28O5S
- Molecular weight
- 380.5
Names & synonyms
Ecabet33159-27-2Ecabetum12-sulfodehydroabietic acidDTXSID70468812K02669KWPDTXCID5026881(1R,4AS,10AR)-1,4A-DIMETHYL-7-(PROPAN-2-YL)-6-SULFO-1,2,3,4,4A,9,10,10A-OCTAHYDROPHENANTHRENE-1-CARBOXYLIC ACID1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-6-sulfo-1-phenanthrenecarboxylic acid 6-sodium saltRefChem:136197Ecabet [INN](1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-6-sulfo-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid
Show more names
Abietic acid, dehydro-6-sulfo- (6CI)Podocarpa-8,11,13-trien-15-oic acid, 13-isopropyl-12-sulfo- (8CI)1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-6-sulfo-, (1R,4aS,10aR)-1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-6-sulfo-, [1R-(1α,4aβ,10aα)]-
Ecabet (INN)13-Isopropyl-12-sulfopodocarpa-8,11,13-trien-15-oic acidC20H28O5SNCGC00181160-01Ecabetum [INN-Latin](1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-6-sulfo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acidUNII-2K02669KWPMFCD11044526
Database identifiers
- CAS
33159-27-2、86408-72-2- PubChem CID
- 65781
- DTXSID
DTXSID7046881- ChEMBL
CHEMBL2104585- ChEBI
CHEBI:135593- UNII
- 2K02669KWP
- Nikkaji
- J550.676J
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 100 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 666
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility4.26e-03 g/L
Physical DescriptionSolid
Physicochemical properties
- alpha
- 25 · D25 +72.4° (c = 2.5 in alcohol)
- Density
- 1.241 · 1.241±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- pka
- -0.31 · -0.31±0.60(Predicted)
- InChIKey
- IWCWQNVIUXZOMJ-MISYRCLQSA-N
- SMILES
- [C@@]1(C)(C(O)=O)[C@@]2([H])[C@@](C)(C3=C(CC2)C=C(C(C)C)C(S(O)(=O)=O)=C3)CCC1
- FDA UNII
- 2 K02669KWP · 2K02669KWP
Chemistry & industry
Pharmacology
Mechanism of Action
Ecabet reduces the survival of H. pylori in the stomach and inhibits pepsin activity in the gastric juice of experimental animals. Here we have investigated the effects of ecabet on some of the factors involved in the dynamics of the mucosal barrier, i.e. pepsins and mucins. Pepsin, acid and Helicobacter pylori are major factors in the pathophysiology of peptic ulcer disease and reflux oesophagitis. Ecabet also acts as an inhibitor of H. pylori NADPH oxidase as well as urease. Inhibition of these enzymes prevents bacterial adhesion to gastric mucosa.
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).
Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
Cellular LocationsCytoplasm
Applications
UsesEcabet sodium (TA-2711) is currently applied to some clinical gastrointestinal disease by inhibiting the ROS production and improving Helicobacter pylori eradication[1]. Ecabet sodium reduces apoptosis[2]
Additional notes
DefinitionChEBI: Ecabet is a diterpenoid.
Related reactions
0 records
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Compound notes
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