NAV

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
3D
Similar Structures
Weight
Average: 270.2369
Monoisotopic: 270.05282343
Chemical Formula
C15H10O5
Synonyms
Not Available
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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
  1. 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]
  2. 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]
  3. 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]
  4. de Witte P, Lemli J: Metabolism of 14C-rhein and 14C-rhein anthrone in rats. Pharmacology. 1988;36 Suppl 1:152-7. [Article]
  5. 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]
  6. 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]
  7. Human Metabolome Database: Rheinanthrone [Link]
Human Metabolome Database
HMDB0039449
PubChem Compound
119396
PubChem Substance
347829279
ChemSpider
106641
BindingDB
50060855
ChEMBL
CHEMBL421615
ZINC
ZINC000001636654

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)250-280Human Metabolome Database [L772]
Predicted Properties
PropertyValueSource
Water Solubility0.122 mg/mLALOGPS
logP2.54ALOGPS
logP3.9Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.54Chemaxon
pKa (Strongest Basic)-5.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area94.83 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity71.53 m3·mol-1Chemaxon
Polarizability26.56 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0fdo-0290000000-3a884ca2c0a98b691ac6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-6ca60abebaa02576367e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-7253723e641702081623
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-ad236f2bed7b93b7c60e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-a8c0b9b80d3596a8ce21
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-054o-0690000000-866a48486bb243a94475
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001s-0910000000-90b565b597b9a6d93906
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-170.3872907
predicted
DarkChem Lite v0.1.0
[M-H]-170.4381907
predicted
DarkChem Lite v0.1.0
[M-H]-170.6676907
predicted
DarkChem Lite v0.1.0
[M-H]-166.07916
predicted
DeepCCS 1.0 (2019)
[M+H]+171.1789907
predicted
DarkChem Lite v0.1.0
[M+H]+170.9791907
predicted
DarkChem Lite v0.1.0
[M+H]+171.4218907
predicted
DarkChem Lite v0.1.0
[M+H]+168.43758
predicted
DeepCCS 1.0 (2019)
[M+Na]+170.6823907
predicted
DarkChem Lite v0.1.0
[M+Na]+171.1911907
predicted
DarkChem Lite v0.1.0
[M+Na]+171.1204907
predicted
DarkChem Lite v0.1.0
[M+Na]+174.53073
predicted
DeepCCS 1.0 (2019)

Drug created at May 19, 2017 15:04 / Updated at June 12, 2020 16:53