Rheinanthrone
Identification
- Generic Name
- Rheinanthrone
- DrugBank Accession Number
- DB13175
- Background
Rheinanthrone is the active metabolite of senna glycoside Sennosides known for its laxative effect 2. It is commonly produced by plants of the Rheum species 7.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 270.2369
Monoisotopic: 270.05282343 - Chemical Formula
- C15H10O5
- Synonyms
- Not Available
Pharmacology
- Indication
No approved indication.
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- Pharmacodynamics
Rheinanthrone stimulates peristalsis and increases fecal water content to increase the movement of feces through the large intestine 1 2.
- Mechanism of action
Rheinanthrone appears to increase macrophage expression of cyclooxygenase 2 (COX2) which increases production of prostaglandin E2 (PGE2) 2. This increase in PGE2 is associated with a subsequent decrease in aquaporin 3 expression. The decreased expression of aquaporin 3 likely restricts reabsorption of water in the large intestine resulting in the laxative effect of rheinanthrone. Rheinanthrone also appears to stimulate peristalsis in the large intestine dependent on contact with the mucosal epithelium 2.
- Absorption
About 10% of rheinanthrone is absorbed from the gut 6.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Once in systemic circulation about 2.6% of rheinanthrone is metabolized to rhein Rhein as well as sennidins A and B via oxidation 3 4.
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- Route of elimination
2.8% of rheinanthrone is excreted in urine and 95% is excreted in feces 6.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Anthracenes
- Sub Class
- Anthracenecarboxylic acids and derivatives
- Direct Parent
- Anthracenecarboxylic acids
- Alternative Parents
- Naphthalenecarboxylic acids / Hydroxybenzoic acid derivatives / Aryl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2-naphthalenecarboxylic acid / 2-naphthalenecarboxylic acid or derivatives / Anthracene carboxylic acid / Aromatic homopolycyclic compound / Aryl ketone / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0YQK3WBH32
- CAS number
- 480-09-1
- InChI Key
- OZFQHULMMDWMIV-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H10O5/c16-10-3-1-2-7-4-8-5-9(15(19)20)6-11(17)13(8)14(18)12(7)10/h1-3,5-6,16-17H,4H2,(H,19,20)
- IUPAC Name
- 4,5-dihydroxy-10-oxo-9,10-dihydroanthracene-2-carboxylic acid
- SMILES
- OC(=O)C1=CC(O)=C2C(CC3=C(C(O)=CC=C3)C2=O)=C1
References
- General References
- Nijs G, de Witte P, Geboes K, Meulemans A, Schuurkes J, Lemli J: Influence of rhein anthrone on peristaltic reflex of guinea-pig isolated ileum: involvement of prostaglandins. Br J Pharmacol. 1993 Jan;108(1):269-73. [Article]
- Kon R, Ikarashi N, Nagoya C, Takayama T, Kusunoki Y, Ishii M, Ueda H, Ochiai W, Machida Y, Sugita K, Sugiyama K: Rheinanthrone, a metabolite of sennoside A, triggers macrophage activation to decrease aquaporin-3 expression in the colon, causing the laxative effect of rhubarb extract. J Ethnopharmacol. 2014 Feb 27;152(1):190-200. doi: 10.1016/j.jep.2013.12.055. Epub 2014 Jan 8. [Article]
- Dreessen M, Eyssen H, Lemli J: The metabolism of sennosides A and B by the intestinal microflora: in vitro and in vivo studies on the rat and the mouse. J Pharm Pharmacol. 1981 Oct;33(10):679-81. [Article]
- de Witte P, Lemli J: Metabolism of 14C-rhein and 14C-rhein anthrone in rats. Pharmacology. 1988;36 Suppl 1:152-7. [Article]
- Zhou YX, Xia W, Yue W, Peng C, Rahman K, Zhang H: Rhein: A Review of Pharmacological Activities. Evid Based Complement Alternat Med. 2015;2015:578107. doi: 10.1155/2015/578107. Epub 2015 Jun 22. [Article]
- De Witte P, Lemli J: Excretion and distribution of [14C]rhein and [14C]rhein anthrone in rat. J Pharm Pharmacol. 1988 Sep;40(9):652-5. [Article]
- Human Metabolome Database: Rheinanthrone [Link]
- External Links
- Human Metabolome Database
- HMDB0039449
- PubChem Compound
- 119396
- PubChem Substance
- 347829279
- ChemSpider
- 106641
- BindingDB
- 50060855
- ChEMBL
- CHEMBL421615
- ZINC
- ZINC000001636654
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 250-280 Human Metabolome Database [L772] - Predicted Properties
Property Value Source Water Solubility 0.122 mg/mL ALOGPS logP 2.54 ALOGPS logP 3.9 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 3.54 Chemaxon pKa (Strongest Basic) -5.6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 94.83 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 71.53 m3·mol-1 Chemaxon Polarizability 26.56 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0fdo-0290000000-3a884ca2c0a98b691ac6 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0090000000-6ca60abebaa02576367e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0090000000-7253723e641702081623 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-ad236f2bed7b93b7c60e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-a8c0b9b80d3596a8ce21 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-054o-0690000000-866a48486bb243a94475 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001s-0910000000-90b565b597b9a6d93906 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 170.3872907 predictedDarkChem Lite v0.1.0 [M-H]- 170.4381907 predictedDarkChem Lite v0.1.0 [M-H]- 170.6676907 predictedDarkChem Lite v0.1.0 [M-H]- 166.07916 predictedDeepCCS 1.0 (2019) [M+H]+ 171.1789907 predictedDarkChem Lite v0.1.0 [M+H]+ 170.9791907 predictedDarkChem Lite v0.1.0 [M+H]+ 171.4218907 predictedDarkChem Lite v0.1.0 [M+H]+ 168.43758 predictedDeepCCS 1.0 (2019) [M+Na]+ 170.6823907 predictedDarkChem Lite v0.1.0 [M+Na]+ 171.1911907 predictedDarkChem Lite v0.1.0 [M+Na]+ 171.1204907 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.53073 predictedDeepCCS 1.0 (2019)
Drug created at May 19, 2017 15:04 / Updated at June 12, 2020 16:53