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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:06 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030636
Secondary Accession Numbers
  • HMDB30636
Metabolite Identification
Common NameBatatasin III
DescriptionBatatasin III belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review a significant number of articles have been published on Batatasin III.
Structure
Data?1563862015
Synonyms
ValueSource
3'-O-Methylbatatasin IIIHMDB
3,3'-Dihydroxy-5-methoxybibenzylHMDB
3-[2-(3-Hydroxyphenyl)ethyl]-5-methoxyphenol, 9ciHMDB
Chemical FormulaC15H16O3
Average Molecular Weight244.2857
Monoisotopic Molecular Weight244.109944378
IUPAC Name3-[2-(3-hydroxyphenyl)ethyl]-5-methoxyphenol
Traditional Name3-[2-(3-hydroxyphenyl)ethyl]-5-methoxyphenol
CAS Registry Number56684-87-8
SMILES
COC1=CC(CCC2=CC(O)=CC=C2)=CC(O)=C1
InChI Identifier
InChI=1S/C15H16O3/c1-18-15-9-12(8-14(17)10-15)6-5-11-3-2-4-13(16)7-11/h2-4,7-10,16-17H,5-6H2,1H3
InChI KeyVYQXIUVIYICVCM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point93.5 - 94.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility48.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
logP3.03ALOGPS
logP3.74ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.82 m³·mol⁻¹ChemAxon
Polarizability26.81 ųChemAxon
Number of Rings2ChemAxon
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]+159.85431661259
DarkChem[M-H]-158.99231661259
DeepCCS[M+H]+161.42930932474
DeepCCS[M-H]-159.07130932474
DeepCCS[M-2H]-191.99930932474
DeepCCS[M+Na]+167.52230932474
AllCCS[M+H]+156.432859911
AllCCS[M+H-H2O]+152.332859911
AllCCS[M+NH4]+160.132859911
AllCCS[M+Na]+161.232859911
AllCCS[M-H]-159.032859911
AllCCS[M+Na-2H]-158.832859911
AllCCS[M+HCOO]-158.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Batatasin IIICOC1=CC(CCC2=CC(O)=CC=C2)=CC(O)=C13773.0Standard polar33892256
Batatasin IIICOC1=CC(CCC2=CC(O)=CC=C2)=CC(O)=C12346.5Standard non polar33892256
Batatasin IIICOC1=CC(CCC2=CC(O)=CC=C2)=CC(O)=C12413.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Batatasin III,1TMS,isomer #1COC1=CC(O)=CC(CCC2=CC=CC(O[Si](C)(C)C)=C2)=C12386.6Semi standard non polar33892256
Batatasin III,1TMS,isomer #2COC1=CC(CCC2=CC=CC(O)=C2)=CC(O[Si](C)(C)C)=C12382.1Semi standard non polar33892256
Batatasin III,2TMS,isomer #1COC1=CC(CCC2=CC=CC(O[Si](C)(C)C)=C2)=CC(O[Si](C)(C)C)=C12301.5Semi standard non polar33892256
Batatasin III,1TBDMS,isomer #1COC1=CC(O)=CC(CCC2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)=C12643.9Semi standard non polar33892256
Batatasin III,1TBDMS,isomer #2COC1=CC(CCC2=CC=CC(O)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C12640.5Semi standard non polar33892256
Batatasin III,2TBDMS,isomer #1COC1=CC(CCC2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)=CC(O[Si](C)(C)C(C)(C)C)=C12796.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Batatasin III GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-1930000000-4e6cfbe01236cca36f892017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Batatasin III GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4319000000-cfbdc5c00ba0486321102017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Batatasin III 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 - Batatasin III , positive-QTOFsplash10-0pi9-2900000000-74270e3e227a56602cc42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Batatasin III 40V, Negative-QTOFsplash10-0a59-0900000000-fccf90bac41e72ac97ba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Batatasin III 20V, Negative-QTOFsplash10-003r-0940000000-3526b19343660f7de5d92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Batatasin III 10V, Negative-QTOFsplash10-0006-0490000000-895cd101a83147a4bea22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 10V, Positive-QTOFsplash10-0002-0090000000-18a6022c7aaa3fbab4a92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 20V, Positive-QTOFsplash10-0002-0590000000-d38568f72b2a5ad492cb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 40V, Positive-QTOFsplash10-00r7-3920000000-06a497b1c52eaa08a2792015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 10V, Negative-QTOFsplash10-0006-0090000000-20de24ec18c0b554de602015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 20V, Negative-QTOFsplash10-0006-0190000000-d68746f34b1ed6b62da92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 40V, Negative-QTOFsplash10-0a6u-4960000000-d21c2bb7bdf92e4d32212015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 10V, Negative-QTOFsplash10-0006-0090000000-705d0952967a1d174ad12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 20V, Negative-QTOFsplash10-052f-0590000000-4bdd942e2ff10bde10192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 40V, Negative-QTOFsplash10-00lr-1930000000-a43c014fc1c7dbfd85922021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 10V, Positive-QTOFsplash10-0002-0490000000-277102ce75f7472b885c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 20V, Positive-QTOFsplash10-0a4m-6920000000-2f16455759d83f5813fd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Batatasin III 40V, Positive-QTOFsplash10-004l-5920000000-9b2e7c166b6e2521b0682021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB002540
KNApSAcK IDC00015292
Chemspider ID8642400
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10466989
PDB IDNot Available
ChEBI ID576152
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1821651
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Batatasin III → 3,4,5-trihydroxy-6-{3-[2-(3-hydroxyphenyl)ethyl]-5-methoxyphenoxy}oxane-2-carboxylic aciddetails
Batatasin III → 3,4,5-trihydroxy-6-{3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]phenoxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Batatasin III → {3-[2-(3-hydroxy-5-methoxyphenyl)ethyl]phenyl}oxidanesulfonic aciddetails