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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:24 UTC
Update Date2022-03-07 02:52:35 UTC
HMDB IDHMDB0030521
Secondary Accession Numbers
  • HMDB30521
Metabolite Identification
Common NameSativan
DescriptionSativan, also known as sativin, belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Sativan has been detected, but not quantified in, several different foods, such as bayberries (Myrica), deerberries (Vaccinium stamineum), cherry tomatoes (Solanum lycopersicum var. cerasiforme), wakames (Undaria pinnatifida), and pepper (capsicum). This could make sativan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sativan.
Structure
Data?1563861998
Synonyms
ValueSource
(-)-SativanHMDB
2'-O-MethylvestitolHMDB
7-Hydroxy-2',4'-dimethoxyisoflavanHMDB
SativinHMDB
Sativin (alfalfa)HMDB
SativanMeSH
Chemical FormulaC17H18O4
Average Molecular Weight286.3224
Monoisotopic Molecular Weight286.120509064
IUPAC Name3-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
Traditional Name3-(2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
CAS Registry Number41743-86-6
SMILES
COC1=CC(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2
InChI Identifier
InChI=1S/C17H18O4/c1-19-14-5-6-15(17(9-14)20-2)12-7-11-3-4-13(18)8-16(11)21-10-12/h3-6,8-9,12,18H,7,10H2,1-2H3
InChI KeyTUXCLJQCYVCGDW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' 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 Parent4'-O-methylated isoflavonoids
Alternative Parents
Substituents
  • 2p-methoxyisoflavonoid-skeleton
  • 4p-methoxyisoflavonoid
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Isoflavan
  • Chromane
  • Benzopyran
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point128 - 129 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.13ALOGPS
logP3.18ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.91 m³·mol⁻¹ChemAxon
Polarizability31.24 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]+169.99331661259
DarkChem[M-H]-169.23831661259
DeepCCS[M+H]+171.32630932474
DeepCCS[M-H]-168.96830932474
DeepCCS[M-2H]-201.85430932474
DeepCCS[M+Na]+177.41930932474
AllCCS[M+H]+167.832859911
AllCCS[M+H-H2O]+164.132859911
AllCCS[M+NH4]+171.232859911
AllCCS[M+Na]+172.232859911
AllCCS[M-H]-172.632859911
AllCCS[M+Na-2H]-172.132859911
AllCCS[M+HCOO]-171.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SativanCOC1=CC(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C23564.5Standard polar33892256
SativanCOC1=CC(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C22517.7Standard non polar33892256
SativanCOC1=CC(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C22711.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sativan,1TMS,isomer #1COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2)C(OC)=C12540.7Semi standard non polar33892256
Sativan,1TBDMS,isomer #1COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)C(OC)=C12802.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sativan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kmr-0490000000-6b04e8d084537d9896532017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sativan GC-MS (1 TMS) - 70eV, Positivesplash10-006x-3539000000-b1ea81d564557fa1a5e52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sativan 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 - Sativan 10V, Positive-QTOFsplash10-0079-0790000000-b7ab2d4a8dde58970e462015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 20V, Positive-QTOFsplash10-00di-0950000000-bc22f47561d65f8a47442015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 40V, Positive-QTOFsplash10-05fr-2920000000-0cadcfa4b764b4a16ae82015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 10V, Negative-QTOFsplash10-000i-0390000000-4e24e908ea01c0359c7d2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 20V, Negative-QTOFsplash10-000i-0690000000-0e475e25503c9eb8fb182015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 40V, Negative-QTOFsplash10-05g0-3950000000-6b150d88620333f6ef7d2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 10V, Negative-QTOFsplash10-000i-0090000000-03e53c541e9b60a095ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 20V, Negative-QTOFsplash10-000i-0290000000-dbae0c5223648a9fb6282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 40V, Negative-QTOFsplash10-000l-2690000000-152d36a273dad8e6e9082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 10V, Positive-QTOFsplash10-000i-0980000000-2c817385f79fb460e7832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 20V, Positive-QTOFsplash10-000i-0970000000-97d2a52de0e8782853fc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sativan 40V, Positive-QTOFsplash10-0kmr-0910000000-f63d928bc349749930a02021-09-23Wishart 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 IDFDB030084
KNApSAcK IDC00002570
Chemspider ID518443
KEGG Compound IDC10526
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound596401
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .