Rhein (CHEM017187)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:59:54 UTC
Update Date2016-11-09 01:15:32 UTC
Accession NumberCHEM017187
Identification
Common NameRhein
ClassSmall Molecule
DescriptionRhein is an anthraquinone metabolite of rheinanthrone and senna glycoside is present in many medicinal plants including Rheum palmatum, Cassia tora, Polygonum multiflorum, and Aloe barbadensis [A19247]. It is known to have hepatoprotective, nephroprotective, anti-cancer, anti-inflammatory, and several other protective effects.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,8-Dihydroxy-3-carboxyl anthraquinoneHMDB
1,8-Dihydroxy-3-carboxyl-9,10-anthraquinoneHMDB, MeSH
1,8-Dihydroxyanthraquinone-3-carboxylic acidHMDB
4, 5-Dihydroxyanthraquinone-2-carboxylic acidHMDB
4,5-Dihydroxy-2-anthraquinonecarboxylic acidHMDB
4,5-DiOH-anthraquinone-2-COOHHMDB
9,10-dihydro-4,5-Dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9ciHMDB
9,10-dihydro-4,5-Dihydroxy-9,10-dioxo-2-anthroic acidHMDB
Cassic acidHMDB
Chrysazin-3-carboxylic acidHMDB
Dipropionyl rheinHMDB, MeSH
MonorheinHMDB
Rhein (1,8-dihydroxy-3-carboxyl anthraquinone)HMDB
Rhubarb yellowHMDB
4,5-Dihydroxyanthraquinone-2-carboxylic acidMeSH, HMDB
Chemical FormulaC15H8O6
Average Molecular Mass284.220 g/mol
Monoisotopic Mass284.032 g/mol
CAS Registry Number478-43-3
IUPAC Name4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
Traditional Namemonorhein
SMILESOC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O
InChI IdentifierInChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
InChI KeyFCDLCPWAQCPTKC-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthracenecarboxylic acids and derivatives
Direct ParentAnthracenecarboxylic acids
Alternative Parents
Substituents
  • Anthracene carboxylic acid
  • 9,10-anthraquinone
  • Anthraquinone
  • 2-naphthalenecarboxylic acid
  • 2-naphthalenecarboxylic acid or derivatives
  • Hydroxybenzoic acid
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.18ALOGPS
logP3.27ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.37 m³·mol⁻¹ChemAxon
Polarizability26.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07cv-0590000000-afcf37d77e69652177f2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-024r-4102900000-c5b546456fd0d7644f8aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0090000000-9ac3e7791e49a21d3f7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0090000000-8a0c3c4f77482fc05626Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0190000000-a217257577bda56ddeb9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0950000000-f5cac5a3a6c78fc4ed85Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0910000000-4671892dc0bcf7214bc0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-5f27d9cb7d81c2b3da8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0190000000-87c468c6073faf9e5faeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0920000000-0b0038f124d8c1494117Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-a2294fd7666d75dbcbd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-052u-0890000000-5f1951e9414e26b22db9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0920000000-5757933ef5a7532b4ef1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-a2294fd7666d75dbcbd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000l-0090000000-a2178fdd7c56081cab09Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-8f070d596b12739e117eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0ac0-0910000000-a9cb6e465076d6963a82Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-2c3cbe9c71ab4af87a66Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0290000000-66c888a0ecf96ae01c8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0920000000-eb6d2ee2a66f5ba2d590Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-467e222d330c2d39d5b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0090000000-6163d091b67836bcff63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0190000000-bd5d0494f66cd7d5828cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-2290000000-33f58cc10ba47d1b818aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-05c98e64e03e092b3975Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0090000000-ec4cf61d964a40527521Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-4390000000-5d5e000d8c2e171dd309Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13174
HMDB IDHMDB0032876
FooDB IDFDB010856
Phenol Explorer IDNot Available
KNApSAcK IDC00002861
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDRHN
Wikipedia LinkRhein
Chemspider ID9762
ChEBI IDNot Available
PubChem Compound ID10168
Kegg Compound IDC10401
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Didry N, Dubreuil L, Pinkas M: Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. Pharmazie. 1994 Sep;49(9):681-3.
2. Stermitz FR, Cashman KK, Halligan KM, Morel C, Tegos GP, Lewis K: Polyacylated neohesperidosides from Geranium caespitosum: bacterial multidrug resistance pump inhibitors. Bioorg Med Chem Lett. 2003 Jun 2;13(11):1915-8.
3. Izzo AA, Mascolo N, Capasso F: Effect of sodium rhein on electrically-evoked and agonist-induced contractions of the guinea-pig isolated ileal circular muscle. Br J Pharmacol. 1998 Jun;124(4):825-31.
4. Kuo PL, Hsu YL, Ng LT, Lin CC: Rhein inhibits the growth and induces the apoptosis of Hep G2 cells. Planta Med. 2004 Jan;70(1):12-6.
5. Chang CY, Chan HL, Lin HY, Way TD, Kao MC, Song MZ, Lin YJ, Lin CW: Rhein induces apoptosis in human breast cancer cells. Evid Based Complement Alternat Med. 2012;2012:952504. doi: 10.1155/2012/952504. Epub 2011 Oct 5.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.