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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:17:37 UTC
Update Date2019-07-23 06:33:01 UTC
HMDB IDHMDB0040717
Secondary Accession Numbers
  • HMDB40717
Metabolite Identification
Common NameAcemannan
DescriptionAcemannan, also known as carrisyn or polymannoacetate, belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Acemannan is an extremely weak basic (essentially neutral) compound (based on its pKa). Acemannan is a D-isomer mucopolysaccharide in aloe vera leaves. Acemannan is currently being used for treatment and clinical management of fibrosarcoma in dogs and cats. This polymer is hydrophilic: It has 50 hydrogen bond acceptors, 19 hydrogen bond donors, and a partition coefficient of -3.27. This compound has been known to have immunostimulant, antiviral, antineoplastic and gastrointestinal properties. These three cytokines are known to cause inflammation, and interferon is released in response to viral infections. The compound has been found to have a LD50 of >80 mg/kg and LC50 >5,000 mg/Kg IV. In vitro studies have shown acemannan to inhibit HIV replication; however, in vivo studies have been inconclusive. Administration of acemannan has been shown to increase tumor necrosis and prolonged host survival; the animals have demonstrated lymphoid infiltration and encapsulation. Therefore, its permeability (and, hence, bioavailability) has been scored to be 1 according to Lipinsky's Rule of Five. Acemannan's monomer is mannoacetate linked by β-1,4-glycosidic bonds.
Structure
Data?1563863581
Synonyms
ValueSource
Acemannan hydrogelHMDB
AcemannananHMDB
alpha-D-Galacto-beta-D-mannan, (1-4),(1-6)-, acetateHMDB
CarrisynHMDB
PolymannoacetateHMDB
CARN 750MeSH
AliminaseMeSH
AlovexMeSH
CARN 1000MeSH
Carrasyn oral wound dressingMeSH
CarryisynMeSH
CARN-1000MeSH
CARN-750MeSH
4-(Acetyloxy)-3-{[4-(acetyloxy)-5-{[4-(acetyloxy)-3-hydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[4-(acetyloxy)-6-[(6-{[4-(acetyloxy)-6-{[4-(acetyloxy)-6-{[4-(acetyloxy)-5-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl)oxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxyoxane-2-carboxylateGenerator
AcemannanMeSH
Chemical FormulaC66H101NO49
Average Molecular Weight1692.492
Monoisotopic Molecular Weight1691.544218636
IUPAC Name4-(acetyloxy)-3-{[4-(acetyloxy)-5-{[4-(acetyloxy)-3-hydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[4-(acetyloxy)-6-[(6-{[4-(acetyloxy)-6-{[4-(acetyloxy)-6-{[4-(acetyloxy)-5-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl)oxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxyoxane-2-carboxylic acid
Traditional Name4-(acetyloxy)-3-{[4-(acetyloxy)-5-{[4-(acetyloxy)-3-hydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[4-(acetyloxy)-6-[(6-{[4-(acetyloxy)-6-{[4-(acetyloxy)-6-{[4-(acetyloxy)-5-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl)oxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxyoxane-2-carboxylic acid
CAS Registry Number110042-95-0
SMILES
COC1OC(CO)C(OC2OC(CO)C(OC3OC(CO)C(OC4OC(CO)C(OC5OC(CO)C(OC6OC(C(OC7OC(CO)C(OC8OC(CO)C(OC)C(OC(C)=O)C8O)C(OC(C)=O)C7O)C(OC(C)=O)C6O)C(O)=O)C(OC(C)=O)C5O)C(O)C4NC(C)=O)C(OC(C)=O)C3O)C(OC(C)=O)C2O)C(OC(C)=O)C1O
InChI Identifier
InChI=1S/C66H101NO49/c1-18(75)67-33-34(83)42(26(11-68)102-59(33)110-44-29(14-71)106-63(38(87)51(44)97-21(4)78)113-46-30(15-72)107-64(39(88)53(46)99-23(6)80)111-45-28(13-70)103-60(94-10)35(84)50(45)96-20(3)77)109-61-37(86)52(98-22(5)79)48(32(17-74)105-61)114-66-41(90)55(101-25(8)82)56(57(116-66)58(91)92)115-65-40(89)54(100-24(7)81)47(31(16-73)108-65)112-62-36(85)49(95-19(2)76)43(93-9)27(12-69)104-62/h26-57,59-66,68-74,83-90H,11-17H2,1-10H3,(H,67,75)(H,91,92)
InChI KeyXOYXESIZZFUVRD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acyl
  • Pyran
  • Oxane
  • Acetamide
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organopnictogen compound
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility29.7 g/LALOGPS
logP-0.4ALOGPS
logP-11ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count42ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area710.86 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity347.35 m³·mol⁻¹ChemAxon
Polarizability160.36 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
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 IDFDB020524
KNApSAcK IDNot Available
Chemspider ID65032
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcemannan
METLIN IDNot Available
PubChem Compound21883405
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Harris C, Pierce K, King G, Yates KM, Hall J, Tizard I: Efficacy of acemannan in treatment of canine and feline spontaneous neoplasms. Mol Biother. 1991 Dec;3(4):207-13. [PubMed:1768373 ]
  2. Sharma JM, Karaca K, Pertile T: Virus-induced immunosuppression in chickens. Poult Sci. 1994 Jul;73(7):1082-6. [PubMed:7937469 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .