Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:41 UTC
Update Date2022-03-07 02:53:04 UTC
HMDB IDHMDB0031657
Secondary Accession Numbers
  • HMDB31657
Metabolite Identification
Common NameFerreirin
DescriptionFerreirin 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. Thus, ferreirin is considered to be a flavonoid. Ferreirin exists in all living organisms, ranging from bacteria to humans. Ferreirin has been detected, but not quantified in, pigeon peas (Cajanus cajan) and pulses. This could make ferreirin a potential biomarker for the consumption of these foods. Ferreirin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Ferreirin.
Structure
Data?1563862153
Synonyms
ValueSource
2,3-Dihydro-5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
2',5,7-Trihydroxy-4'-methoxyisoflavanoneHMDB
Chemical FormulaC16H14O6
Average Molecular Weight302.2788
Monoisotopic Molecular Weight302.07903818
IUPAC Name5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Nameferreirin
CAS Registry Number32898-79-6
SMILES
COC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O
InChI Identifier
InChI=1S/C16H14O6/c1-21-9-2-3-10(12(18)6-9)11-7-22-14-5-8(17)4-13(19)15(14)16(11)20/h2-6,11,17-19H,7H2,1H3
InChI KeyCBEPNYOFLRIAGR-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
  • 4p-methoxyisoflavonoid
  • Isoflavanol
  • Isoflavanone
  • Hydroxyisoflavonoid
  • Isoflavan
  • Chromone
  • Methoxyphenol
  • Benzopyran
  • 1-benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point210 - 212 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility226.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.49ALOGPS
logP2.57ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.88ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.14 m³·mol⁻¹ChemAxon
Polarizability29.45 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]+168.84631661259
DarkChem[M-H]-171.76731661259
DeepCCS[M+H]+169.90330932474
DeepCCS[M-H]-167.54530932474
DeepCCS[M-2H]-200.43130932474
DeepCCS[M+Na]+175.99630932474
AllCCS[M+H]+169.932859911
AllCCS[M+H-H2O]+166.332859911
AllCCS[M+NH4]+173.332859911
AllCCS[M+Na]+174.232859911
AllCCS[M-H]-171.432859911
AllCCS[M+Na-2H]-170.932859911
AllCCS[M+HCOO]-170.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FerreirinCOC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O4136.9Standard polar33892256
FerreirinCOC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O2973.2Standard non polar33892256
FerreirinCOC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O3047.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ferreirin,1TMS,isomer #1COC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C(O[Si](C)(C)C)=C12901.8Semi standard non polar33892256
Ferreirin,1TMS,isomer #2COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C(O)=C12912.5Semi standard non polar33892256
Ferreirin,1TMS,isomer #3COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C(O)=C12952.6Semi standard non polar33892256
Ferreirin,2TMS,isomer #1COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C(O[Si](C)(C)C)=C12794.1Semi standard non polar33892256
Ferreirin,2TMS,isomer #2COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C12880.3Semi standard non polar33892256
Ferreirin,2TMS,isomer #3COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C(O)=C12869.3Semi standard non polar33892256
Ferreirin,3TMS,isomer #1COC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C12765.4Semi standard non polar33892256
Ferreirin,1TBDMS,isomer #1COC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13168.5Semi standard non polar33892256
Ferreirin,1TBDMS,isomer #2COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C(O)=C13169.6Semi standard non polar33892256
Ferreirin,1TBDMS,isomer #3COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C13211.9Semi standard non polar33892256
Ferreirin,2TBDMS,isomer #1COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13299.7Semi standard non polar33892256
Ferreirin,2TBDMS,isomer #2COC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13355.4Semi standard non polar33892256
Ferreirin,2TBDMS,isomer #3COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C13361.5Semi standard non polar33892256
Ferreirin,3TBDMS,isomer #1COC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13466.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ferreirin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0971000000-e1a752f1fe5e5bef99b12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ferreirin GC-MS (3 TMS) - 70eV, Positivesplash10-0w91-2790650000-726641b201ef5d1f317f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ferreirin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ferreirin 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 - Ferreirin 10V, Positive-QTOFsplash10-0udi-0439000000-c432e250004639a5b97a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 20V, Positive-QTOFsplash10-0udr-0933000000-f509a1599d51f22e9c872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 40V, Positive-QTOFsplash10-0f79-2910000000-9f49b49b0b8876d88ff12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 10V, Negative-QTOFsplash10-0udi-0019000000-984f80d99703c2cf5dd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 20V, Negative-QTOFsplash10-0udi-1879000000-cd7addbf04b682ec99982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 40V, Negative-QTOFsplash10-006x-9620000000-f191e4817cbcda7e0cf82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 10V, Negative-QTOFsplash10-0udi-0109000000-ca8f0442f17fc86c01ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 20V, Negative-QTOFsplash10-0udi-0598000000-852bb2bbf10d2bceeb652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 40V, Negative-QTOFsplash10-0uxr-1390000000-18a196624ec42760dd4a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 10V, Positive-QTOFsplash10-0ufr-0907000000-a782d3f05e3c9b06fc832021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 20V, Positive-QTOFsplash10-0udj-0901000000-15d93d0c4825184dd82e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ferreirin 40V, Positive-QTOFsplash10-1009-3920000000-30644f950f2320dc8b6b2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB008317
KNApSAcK IDC00002524
Chemspider ID391111
KEGG Compound IDC10419
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442771
PDB IDNot Available
ChEBI ID5018
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1827331
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
Ferreirin → 3,4,5-trihydroxy-6-{[7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic aciddetails
Ferreirin → 3,4,5-trihydroxy-6-{[5-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic aciddetails
Ferreirin → 6-[2-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)-5-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails