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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:17 UTC
Update Date2022-03-07 02:52:43 UTC
HMDB IDHMDB0030829
Secondary Accession Numbers
  • HMDB30829
Metabolite Identification
Common NameAloeemodin
DescriptionAloeemodin, also known as rhabarberone or rottlerin?, 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. Thus, aloeemodin is considered to be an aromatic polyketide. Aloeemodin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Aloeemodin.
Structure
Data?1563862044
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 Weight270.2369
Monoisotopic Molecular Weight270.05282343
IUPAC Name1,8-dihydroxy-3-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione
Traditional Namealoe emodin
CAS Registry Number481-72-1
SMILES
OCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point221 - 223 °CNot Available
Boiling Point568.82 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility45.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.254 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+162.72831661259
DarkChem[M-H]-161.82231661259
DeepCCS[M+H]+161.22330932474
DeepCCS[M-H]-158.86530932474
DeepCCS[M-2H]-191.85730932474
DeepCCS[M+Na]+167.31630932474
AllCCS[M+H]+160.332859911
AllCCS[M+H-H2O]+156.532859911
AllCCS[M+NH4]+163.832859911
AllCCS[M+Na]+164.832859911
AllCCS[M-H]-161.732859911
AllCCS[M+Na-2H]-161.032859911
AllCCS[M+HCOO]-160.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AloeemodinOCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O3804.4Standard polar33892256
AloeemodinOCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O2503.2Standard non polar33892256
AloeemodinOCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O2720.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aloeemodin,1TMS,isomer #1C[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C12681.5Semi standard non polar33892256
Aloeemodin,1TMS,isomer #2C[Si](C)(C)OC1=CC(CO)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O2647.3Semi standard non polar33892256
Aloeemodin,1TMS,isomer #3C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O2666.6Semi standard non polar33892256
Aloeemodin,2TMS,isomer #1C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C12683.7Semi standard non polar33892256
Aloeemodin,2TMS,isomer #2C[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C12707.7Semi standard non polar33892256
Aloeemodin,2TMS,isomer #3C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(CO)C=C1C2=O2664.2Semi standard non polar33892256
Aloeemodin,3TMS,isomer #1C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C12735.7Semi standard non polar33892256
Aloeemodin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C12943.2Semi standard non polar33892256
Aloeemodin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(CO)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O2905.1Semi standard non polar33892256
Aloeemodin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O2923.3Semi standard non polar33892256
Aloeemodin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C13132.2Semi standard non polar33892256
Aloeemodin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C(=O)C2=C13181.9Semi standard non polar33892256
Aloeemodin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(CO)C=C1C2=O3167.9Semi standard non polar33892256
Aloeemodin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C(=O)C2=C13385.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aloeemodin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-0490000000-0bd7d78de4ab72cee4992017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aloeemodin GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9335800000-8354afcd5801dd9e226a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aloeemodin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 45V, Positive-QTOFsplash10-00di-0090000000-89a9cdbc914be4f31ef02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 30V, Negative-QTOFsplash10-014i-0900000000-1f7f05d70e145262a8ae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 50V, Negative-QTOFsplash10-014i-0900000000-2ae7958aaa49742624362021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 60V, Positive-QTOFsplash10-00di-1890000000-1bcbfa331cd0f56b05192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 90V, Positive-QTOFsplash10-014i-9700000000-1b6342ee504925cf87122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 75V, Positive-QTOFsplash10-0gi0-4910000000-2e7abe7e97dced7a4fd62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 15V, Positive-QTOFsplash10-00di-0090000000-2f4d012dbc11d78cb7fd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 30V, Positive-QTOFsplash10-00di-0090000000-ae6e5e86465295cd03322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 6V, Positive-QTOFsplash10-014i-0090000000-33131ad58113b1ea5a1a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 50V, Positive-QTOFsplash10-0f6x-5900000000-421c17b03cf15fb796292021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 30V, Positive-QTOFsplash10-0fk9-1970000000-869440dbcfb69ad60b6c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 10V, Positive-QTOFsplash10-00di-0190000000-93b116cb88147c1246f82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 10V, Positive-QTOFsplash10-00di-0090000000-a08aa7ee329d4ff27f602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 50V, Positive-QTOFsplash10-0gbc-5900000000-e0ea1aecea08fb1b67bb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 6V, Positive-QTOFsplash10-014i-0900000000-8453dca9bdc4d7faec672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 30V, Positive-QTOFsplash10-0fk9-0970000000-ef8922c4a65810a2f2c92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 30V, Positive-QTOFsplash10-0fk9-0960000000-e84a183db3b91f5702da2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 6V, Positive-QTOFsplash10-0udi-0090000000-d2f0783b46bac268d0df2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aloeemodin 50V, Positive-QTOFsplash10-0gbc-4900000000-f81771cbd943d04185442021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aloeemodin 10V, Positive-QTOFsplash10-00di-0090000000-0e840b8245048a00c03d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aloeemodin 20V, Positive-QTOFsplash10-0fk9-0690000000-b4decba7d1a8791488402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aloeemodin 40V, Positive-QTOFsplash10-0uk9-6980000000-d1cc4a7d015592f258212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aloeemodin 10V, Negative-QTOFsplash10-014i-0090000000-c444047e5e27050701b92016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aloeemodin 20V, Negative-QTOFsplash10-014r-0090000000-1c009306edea3d4227b82016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aloeemodin 40V, Negative-QTOFsplash10-000l-5590000000-ac4566b9723c0c91620c2016-08-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002785
KNApSAcK IDC00002789
Chemspider ID9792
KEGG Compound IDC10294
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAloe_emodin
METLIN IDNot Available
PubChem Compound10207
PDB IDNot Available
ChEBI ID2607
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1665291
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:3237568 ]
  2. Heidemann A, Volkner W, Mengs U: Genotoxicity of aloeemodin in vitro and in vivo. Mutat Res. 1996 Mar 1;367(3):123-33. [PubMed:8600368 ]
  3. 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. [PubMed:9415207 ]
  4. 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. [PubMed:20521549 ]
  5. 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. [PubMed:20872909 ]
  6. 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. [PubMed:10521682 ]
  7. 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. [PubMed:23455673 ]
  8. 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. [PubMed:11731923 ]
  9. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .