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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:24:43 UTC
Update Date2022-03-07 02:55:38 UTC
HMDB IDHMDB0038128
Secondary Accession Numbers
  • HMDB38128
Metabolite Identification
Common Name(±)-Sphaerosin
Description(±)-Sphaerosin belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, (±)-sphaerosin is considered to be a flavonoid (±)-Sphaerosin has been detected, but not quantified in, several different foods, such as common beans (Phaseolus vulgaris), green beans (Phaseolus vulgaris), hyacinth beans (Lablab purpureus), pulses, and yellow wax beans (Phaseolus vulgaris). This could make (±)-sphaerosin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-Sphaerosin.
Structure
Data?1563863144
Synonyms
ValueSource
(+/-)-sphaerosinHMDB
7,4'-Dihydroxy-2',3'-dimethoxyisoflavanHMDB
LaxifloranHMDB
Chemical FormulaC17H18O5
Average Molecular Weight302.3218
Monoisotopic Molecular Weight302.115423686
IUPAC Name3-(4-hydroxy-2,3-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
Traditional Namesphaerosin
CAS Registry Number52305-06-3
SMILES
COC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC
InChI Identifier
InChI=1S/C17H18O5/c1-20-16-13(5-6-14(19)17(16)21-2)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3
InChI KeyHHNUTZFOMIAQMX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C3' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent3'-O-methylated isoflavonoids
Alternative Parents
Substituents
  • 2p-methoxyisoflavonoid-skeleton
  • 3p-methoxyisoflavonoid-skeleton
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Isoflavan
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 - 171 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility109.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP2.83ALOGPS
logP2.88ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.65ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.89 m³·mol⁻¹ChemAxon
Polarizability32.01 ųChemAxon
Number of Rings3ChemAxon
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]+170.16931661259
DarkChem[M-H]-170.30231661259
DeepCCS[M+H]+173.2130932474
DeepCCS[M-H]-170.85230932474
DeepCCS[M-2H]-204.14830932474
DeepCCS[M+Na]+179.37430932474
AllCCS[M+H]+170.932859911
AllCCS[M+H-H2O]+167.332859911
AllCCS[M+NH4]+174.232859911
AllCCS[M+Na]+175.132859911
AllCCS[M-H]-174.932859911
AllCCS[M+Na-2H]-174.532859911
AllCCS[M+HCOO]-174.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-SphaerosinCOC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC3749.1Standard polar33892256
(??)-SphaerosinCOC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC2648.8Standard non polar33892256
(??)-SphaerosinCOC1=C(O)C=CC(C2COC3=C(C2)C=CC(O)=C3)=C1OC2837.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)-Sphaerosin,1TMS,isomer #1COC1=C(O[Si](C)(C)C)C=CC(C2COC3=CC(O)=CC=C3C2)=C1OC2739.2Semi standard non polar33892256
(??)-Sphaerosin,1TMS,isomer #2COC1=C(O)C=CC(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2)=C1OC2617.5Semi standard non polar33892256
(??)-Sphaerosin,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=CC(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2)=C1OC2622.9Semi standard non polar33892256
(??)-Sphaerosin,1TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2COC3=CC(O)=CC=C3C2)=C1OC2989.8Semi standard non polar33892256
(??)-Sphaerosin,1TBDMS,isomer #2COC1=C(O)C=CC(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)=C1OC2861.7Semi standard non polar33892256
(??)-Sphaerosin,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)=C1OC3054.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Sphaerosin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0691000000-addfc61017b8e4cc49cb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Sphaerosin GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-2123900000-f06f1cc1a404585ca0982017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Sphaerosin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Sphaerosin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 10V, Positive-QTOFsplash10-0uk9-0918000000-31b4fc6f362560229ac22016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 20V, Positive-QTOFsplash10-00di-0941000000-d7d8eaeb1453d0ffdda52016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 40V, Positive-QTOFsplash10-05fr-4900000000-c0fee25bcc919ba9be322016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 10V, Negative-QTOFsplash10-0udi-0319000000-c305dd626dae3cc018e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 20V, Negative-QTOFsplash10-0udi-0964000000-f7b1b7f58d29117107852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 40V, Negative-QTOFsplash10-00di-2940000000-586c4d9999236b0c383d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 10V, Positive-QTOFsplash10-0udi-0809000000-ca46340f673cd477dd192021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 20V, Positive-QTOFsplash10-0udj-0904000000-2348a04dac2eb134a1cc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 40V, Positive-QTOFsplash10-05gj-0910000000-6a1b4dab8415324b6a792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 10V, Negative-QTOFsplash10-0udi-0009000000-65359146e4ae89379a4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 20V, Negative-QTOFsplash10-0udi-0689000000-18775aae706dce95e95b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Sphaerosin 40V, Negative-QTOFsplash10-052r-2930000000-816622cd98b89a175a402021-09-24Wishart 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 IDFDB017355
KNApSAcK IDC00009717
Chemspider ID153700
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound176471
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1865971
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.. .