Back to Compounds

Showing Compound Asperuloside (FDB007455)

Record Information
Version1.0
Creation date2010-04-08 22:07:37 UTC
Update date2025-11-18 23:04:51 UTC
Primary IDFDB007455
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAsperuloside
DescriptionAsperuloside is a member of the class of compounds known as O-glycosyl compounds. O-glycosyl compounds are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Asperuloside is soluble (in water) and a very weakly acidic compound (based on its pKa). Asperuloside can be found in bilberry, which makes asperuloside a potential biomarker for the consumption of this food product.
CAS Number14259-45-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Asperulosidebiospider
Predicted Properties
PropertyValueSource
Water Solubility17.5 g/LALOGPS
logP-1ALOGPS
logP-2.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)5.44ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area161.21 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.84 m³·mol⁻¹ChemAxon
Polarizability38.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H22O11
IUPAC name[(4S,7S,8S,11S)-2-oxo-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]undeca-1(10),5-dien-6-yl]methyl acetate
InChI IdentifierInChI=1S/C18H22O11/c1-6(20)25-4-7-2-9-12-8(16(24)27-9)5-26-17(11(7)12)29-18-15(23)14(22)13(21)10(3-19)28-18/h2,5,9-15,17-19,21-23H,3-4H2,1H3/t9-,10+,11+,12-,13+,14-,15+,17-,18-/m0/s1
InChI KeyIBIPGYWNOBGEMH-DILZHRMZSA-N
Isomeric SMILESCC(=O)OCC1=C[C@@H]2OC(=O)C3=CO[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]1[C@H]23
Average Molecular Weight414.3607
Monoisotopic Molecular Weight414.116211546
Classification
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • Hexose monosaccharide
  • O-glycosyl compound
  • Furopyran
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Monosaccharide
  • Oxane
  • Pyran
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Furan
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Oxacycle
  • Acetal
  • Primary alcohol
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point131.5 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0794200000-ae4be157e61f633a75932016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lyd-0791000000-ce2ec3e10f40a7c37e582016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2920000000-a3a1c3a2147f7adfc1462016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0nmi-5294400000-3b99a9de99116c3b17a42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-8693000000-67716769e777d471efd12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbc-9460000000-93dbde479fad95c184d82016-08-03View Spectrum
NMRNot Available
ChemSpider ID76046
ChEMBL IDCHEMBL461910
KEGG Compound IDC09769
Pubchem Compound ID84298
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDASPERULOSIDE
BIGG IDNot Available
KNApSAcK IDC00003072
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-clastogenAn agent that inhibits mutagenic agents, preventing chromosome breakage and disruption, used to reduce genetic damage and cancer risk, with therapeutic applications in cancer prevention and treatment, and key medical uses in protecting against radiation and chemical-induced DNA damage.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti neoplastic35610 An agent that inhibits or suppresses the growth and proliferation of cancer cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce apoptosis, prevent tumor progression, and enhance patient survival. Key medical uses include chemotherapy, radiation therapy, and targeted therapy for various types of cancer, such as leukemia, breast, lung, and colon cancer.DUKE
Cathartic75325 An agent that induces bowel movements, relieving constipation by stimulating intestinal motility. Its biological role is to increase water and electrolyte secretion in the gut. Therapeutically, cathartics are used to treat constipation, prepare the bowel for surgery or exams, and manage opioid-induced constipation. Key medical uses include laxative therapy and colonoscopy preparation.DUKE
Herbicide24527 A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Laxative50503 An agent that stimulates bowel movements, relieving constipation by softening stool or increasing intestinal motility. Therapeutically, laxatives are used to treat constipation, prepare the bowel for medical procedures, and manage certain medical conditions, such as irritable bowel syndrome.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).