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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:41:42 UTC
Update Date2021-09-14 15:39:02 UTC
HMDB IDHMDB0041832
Secondary Accession Numbers
  • HMDB41832
Metabolite Identification
Common NameBaicalin
DescriptionBaicalin belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Baicalin is an extremely weak basic (essentially neutral) compound (based on its pKa). It induces apoptosis in pancreatic cancer cells. In mice, baicalin produces anxiolytic effects without sedative or myorelaxant effects. It is one of the chemical ingredients of Sho-Saiko-To, an herbal supplement. It is the glucuronide of baicalein. It is thought that baicalin, along with other flavonoids, may underlie the anxiolytic effects of S. baicalensis and S. lateriflora. Baicalin is a flavone glycoside. Baicalin, along with its aglycone baicalein, is a positive allosteric modulator of the benzodiazepine site and/or a non-benzodiazepine site of the GABAA receptor.
Structure
Data?1563863706
Synonyms
ValueSource
5,6,7-Trihydroxyflavone 7-O-beta-D-glucuronideHMDB
5,6-Dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl beta-D-glucopyranosiduronic acidHMDB
5,6-Dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl beta-D-glucopyranosiduronic acidHMDB
7-D-Glucuronic acid-5,6-dihydroxyflavoneHMDB
Baicalein 7-O-glucuronideHMDB
(2S,3S,4S,5R,6R)-6-[(5,6-Dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC21H18O11
Average Molecular Weight446.361
Monoisotopic Molecular Weight446.084911418
IUPAC Name(2S,3S,4S,5R,6R)-6-[(5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-6-[(5,6-dihydroxy-4-oxo-2-phenylchromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number21967-41-9
SMILES
O[C@@H]1[C@@H](O)[C@@H](OC2=C(O)C(O)=C3C(=O)C=C(OC3=C2)C2=CC=CC=C2)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21-/m0/s1
InChI KeyIKIIZLYTISPENI-UNJWAJPSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • 5-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Beta-hydroxy acid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point202 - 205 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.72 g/LALOGPS
logP1.27ALOGPS
logP0.76ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)2.62ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.93 m³·mol⁻¹ChemAxon
Polarizability42.03 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available204.1531661259
DarkChem[M-H]-PredictedNot Available197.2431661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Baicalin,1TMS,#13872.3135https://arxiv.org/abs/1905.12712
Baicalin,1TMS,#23897.164https://arxiv.org/abs/1905.12712
Baicalin,1TMS,#33932.2773https://arxiv.org/abs/1905.12712
Baicalin,1TMS,#43930.7993https://arxiv.org/abs/1905.12712
Baicalin,1TMS,#53908.4414https://arxiv.org/abs/1905.12712
Baicalin,1TMS,#63926.4905https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#13810.4492https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#23803.0671https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#33799.2322https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#43790.9775https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#53796.5706https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#63810.2688https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#73830.1946https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#83817.9631https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#93813.0415https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#103850.8618https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#113830.577https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#123859.6597https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#133867.1135https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#143836.7856https://arxiv.org/abs/1905.12712
Baicalin,2TMS,#153859.0083https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#13806.7192https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#23783.8657https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#33768.8633https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#43782.808https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#53806.9739https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#63785.377https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#73784.8784https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#83789.2646https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#93776.008https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#103757.6416https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#113825.9434https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#123791.7546https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#133780.6013https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#143827.949https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#153805.4146https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#163802.677https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#173845.9846https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#183823.8025https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#193820.2976https://arxiv.org/abs/1905.12712
Baicalin,3TMS,#203850.2732https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#13827.5256https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#23799.864https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#33825.2446https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#43803.5999https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#53789.3962https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#63773.687https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#73808.2188https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#83809.612https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#93786.4524https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#103791.5554https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#113850.41https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#123836.1877https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#133808.525https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#143837.367https://arxiv.org/abs/1905.12712
Baicalin,4TMS,#153853.7595https://arxiv.org/abs/1905.12712
Baicalin,5TMS,#13807.7493https://arxiv.org/abs/1905.12712
Baicalin,5TMS,#23833.5608https://arxiv.org/abs/1905.12712
Baicalin,5TMS,#33827.962https://arxiv.org/abs/1905.12712
Baicalin,5TMS,#43803.0862https://arxiv.org/abs/1905.12712
Baicalin,5TMS,#53803.558https://arxiv.org/abs/1905.12712
Baicalin,5TMS,#63838.9985https://arxiv.org/abs/1905.12712
Baicalin,6TMS,#13834.98https://arxiv.org/abs/1905.12712
Baicalin,1TBDMS,#14117.616https://arxiv.org/abs/1905.12712
Baicalin,1TBDMS,#24146.464https://arxiv.org/abs/1905.12712
Baicalin,1TBDMS,#34167.1343https://arxiv.org/abs/1905.12712
Baicalin,1TBDMS,#44190.343https://arxiv.org/abs/1905.12712
Baicalin,1TBDMS,#54136.439https://arxiv.org/abs/1905.12712
Baicalin,1TBDMS,#64191.8325https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#14247.8066https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#24283.3066https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#34286.0215https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#44267.9917https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#54238.141https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#64247.335https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#74309.1284https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#84300.561https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#94280.0493https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#104320.6133https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#114280.57https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#124310.9575https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#134349.0376https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#144304.653https://arxiv.org/abs/1905.12712
Baicalin,2TBDMS,#154318.733https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#14439.264https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#24439.667https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#34445.5884https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#44403.332https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#54470.302https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#64462.949https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#74431.304https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#84423.481https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#94429.916https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#104437.832https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#114479.6333https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#124454.511https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#134455.083https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#144493.9033https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#154485.8667https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#164435.757https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#174479.5493https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#184488.1934https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#194437.2104https://arxiv.org/abs/1905.12712
Baicalin,3TBDMS,#204492.397https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05di-9328400000-21f478bcb7bb93e5bf282017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-3392057000-ae58abaf7f516069457c2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-05di-9328400000-21f478bcb7bb93e5bf282021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0090800000-605bcbd2ffd9fc7890f22017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-f684485fa58df61301462017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w90-1590000000-6a6f69daef985731b73d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-1251900000-33775a5cd1996ce659d32017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2291200000-5a566a74a1bcab99fdb52017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-4590000000-56ad61dab640ec2290f32017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dj-0090400000-10e70971051c82d629462021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-60b322ff74af8a7655802021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0090000000-53bc3f6f773ee367b5a92021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0090600000-aaea534c6c95d07377be2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-0f9cf513153f5787dba62021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0090000000-74726919fa50baee16372021-09-08View Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID16498738
KEGG Compound IDC10025
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBaicalin
METLIN IDNot Available
PubChem Compound13654833
PDB IDNot Available
ChEBI ID2981
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available