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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:17 UTC
Update Date2021-10-13 06:11:14 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
Disposition

Biological location

Source

Route of exposure

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 Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP10(2.39) g/LALOGPS
logP10(2.84) g/LChemAxon
logS10(-3) g/LALOGPS
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 Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+162.72831661259
DarkChem[M-H]-161.82231661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aloeemodin,1TMS,#1C[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C12681.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,1TMS,#2C[Si](C)(C)OC1=CC(CO)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O2647.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,1TMS,#3C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O2666.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,2TMS,#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 polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,2TMS,#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 polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,2TMS,#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 polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,3TMS,#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 polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,1TBDMS,#1CC(C)(C)[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C12943.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,1TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC(CO)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O2905.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O2923.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,2TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,2TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,2TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
Aloeemodin,3TBDMS,#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 polarhttps://arxiv.org/abs/1905.12712
Spectra
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.. .