Aloe-emodin (CHEM017313)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:14:12 UTC
Update Date2016-11-09 01:15:34 UTC
Accession NumberCHEM017313
Identification
Common NameAloe-emodin
ClassSmall Molecule
DescriptionA dihydroxyanthraquinone that is chrysazin carrying a hydroxymethyl group at position 3. It has been isolated from plant species of the genus Aloe.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,8-Dihydroxy-3-hydroxymethylanthraquinoneChEBI
3-(Hydroxymethyl)chrysazinChEBI
Aloe-emodinChEBI
RhabarberoneChEBI
1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthracenedioneHMDB
1,8-Dihydroxy-3-(hydroxymethyl)anthra-9,10-quinoneHMDB
1,8-Dihydroxy-3-(hydroxymethyl)anthraquinoneHMDB
1,8-Dihydroxy-3-hydroxymethyl-9,10-anthracenedione, 9ciHMDB
1,8-Dihydroxy-3-hydroxymethyl-anthraquinoneHMDB
3-HydroxymethylchrysazineHMDB
Rottlerin?HMDB
Aloe emodinHMDB
AloeemodinChEBI
Chemical FormulaC15H10O5
Average Molecular Mass270.237 g/mol
Monoisotopic Mass270.053 g/mol
CAS Registry Number481-72-1
IUPAC Name1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione
Traditional Namealoe emodin
SMILESOCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O
InChI IdentifierInChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2
InChI KeyYDQWDHRMZQUTBA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentAnthraquinones
Alternative Parents
Substituents
  • Anthraquinone
  • 9,10-anthraquinone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.3 g/LALOGPS
logP2.39ALOGPS
logP2.84ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.93 m³·mol⁻¹ChemAxon
Polarizability26.51 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, Positivesplash10-0f6x-0490000000-0bd7d78de4ab72cee499Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9335800000-8354afcd5801dd9e226aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00di-0090000000-89a9cdbc914be4f31ef0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-0900000000-1f7f05d70e145262a8aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-014i-0900000000-2ae7958aaa4974262436Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00di-1890000000-1bcbfa331cd0f56b0519Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-014i-9700000000-1b6342ee504925cf8712Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0gi0-4910000000-2e7abe7e97dced7a4fd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-00di-0090000000-2f4d012dbc11d78cb7fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0090000000-ae6e5e86465295cd0332Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0090000000-33131ad58113b1ea5a1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0f6x-5900000000-421c17b03cf15fb79629Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0fk9-1970000000-869440dbcfb69ad60b6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-93b116cb88147c1246f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-a08aa7ee329d4ff27f60Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0gbc-5900000000-e0ea1aecea08fb1b67bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-8453dca9bdc4d7faec67Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0fk9-0970000000-ef8922c4a65810a2f2c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0fk9-0960000000-e84a183db3b91f5702daSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0090000000-d2f0783b46bac268d0dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0gbc-4900000000-f81771cbd943d0418544Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-0e840b8245048a00c03dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0690000000-b4decba7d1a879148840Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-6980000000-d1cc4a7d015592f25821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-c444047e5e27050701b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0090000000-1c009306edea3d4227b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-5590000000-ac4566b9723c0c91620cSpectrum
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 IDNot Available
HMDB IDHMDB0030829
FooDB IDFDB002785
Phenol Explorer IDNot Available
KNApSAcK IDC00002789
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAloe_emodin
Chemspider ID9792
ChEBI ID2607
PubChem Compound ID10207
Kegg Compound IDC10294
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22931417
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24685589
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24707862
4. Paszkiewicz-Gadek A, Chlabicz J, Galasinski W: The influence of selected potential oncostatics of plant origin on the protein biosynthesis in vitro. Pol J Pharmacol Pharm. 1988 Mar-Apr;40(2):183-90.
5. Heidemann A, Volkner W, Mengs U: Genotoxicity of aloeemodin in vitro and in vivo. Mutat Res. 1996 Mar 1;367(3):123-33.
6. Galasinski W, Chlabicz J, Paszkiewicz-Gadek A, Marcinkiewicz C, Gindzienski A: The substances of plant origin that inhibit protein biosynthesis. Acta Pol Pharm. 1996 Sep-Oct;53(5):311-8.
7. Xu F, Liu Y, Dong H, Song R, Zhang Z: Pharmacokinetic comparison in rats of six bioactive compounds between Da-Cheng-Qi decoction and its parent herbal medicines. Nat Prod Commun. 2010 May;5(5):795-800.
8. Zan B, Shi R, Wang T, Wu J, Ma Y, Cheng N: Simultaneous quantification of multiple active components from Xiexin decoction in rat plasma by LC-ESI-MS/MS: application in pharmacokinetics. Biomed Chromatogr. 2011 Jul;25(7):816-26. doi: 10.1002/bmc.1521. Epub 2010 Sep 27.
9. Mengs U, Grimminger W, Krumbiegel G, Schuler D, Silber W, Volkner W: No clastogenic activity of a senna extract in the mouse micronucleus assay. Mutat Res. 1999 Aug 18;444(2):421-6.
10. Dong XJ, Zhu YF, Bao GH, Hu FL, Qin GW: New limonoids and a dihydrobenzofuran norlignan from the roots of Toona sinensis. Molecules. 2013 Mar 1;18(3):2840-50. doi: 10.3390/molecules18032840.
11. Saleem R, Faizi S, Siddiqui BS, Ahmed M, Hussain SA, Qazi A, Dar A, Ahmad SI, Qazi MH, Akhtar S, Hasnain SN: Hypotensive effect of chemical constituents from Aloe barbadensis. Planta Med. 2001 Nov;67(8):757-60.
12. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.