Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-02-24 19:10:38 UTC
Primary IDFDB002801
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameApiin
DescriptionApiin belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. Apiin is found, on average, in the highest concentration within a few different foods, such as wild celeries (Apium graveolens), celery leaves (Apium graveolens var. secalinum), and lentils (Lens culinaris). Apiin has also been detected, but not quantified in, several different foods, such as yellow bell peppers (Capsicum annuum), german camomiles (Matricaria recutita), orange bell peppers (Capsicum annuum), roman camomiles (Chamaemelum nobile), and chervils (Anthriscus cerefolium). This could make apiin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Apiin.
CAS Number26544-34-3
Structure
Thumb
Synonyms
SynonymSource
7-(2-Apiosylglucosyl)apigeninHMDB
Apigenin 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside]HMDB
Apigenin-7-apioglucosideHMDB
ApiosideHMDB
ApiinMeSH
6''-AcetylapiinMeSH
Predicted Properties
PropertyValueSource
Water Solubility1.53 g/LALOGPS
logP-0.17ALOGPS
logP-0.84ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity131.73 m³·mol⁻¹ChemAxon
Polarizability55.4 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H28O14
IUPAC name7-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2
InChI KeyNTDLXWMIWOECHG-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)C(OC2OCC(O)(CO)C2O)C(O)C1O
Average Molecular Weight564.4921
Monoisotopic Molecular Weight564.147905604
Classification
Description Belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassPhenylnaphthalenes
Direct ParentPhenylnaphthalenes
Alternative Parents
Substituents
  • Phenylnaphthalene
  • Phenalen-1-one
  • Phenalen
  • Aryl ketone
  • Monocyclic benzene moiety
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.32%; H 5.00%; O 39.68%DFC
Melting PointMp 236-237°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -130 (c, 0.12 in MeOH)DFC
Spectroscopic UV Data342 (e 19950) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSApiin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007k-7230390000-be49fba592c5fd103da4Spectrum
Predicted GC-MSApiin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9201006000-59afb33788ee043a12c6Spectrum
Predicted GC-MSApiin, "Apiin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiin, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0000090000-a04baa45f6225c583e5aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03xr-0070090000-8047ba073b20f04775e5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0010090000-3283a550fcfc4f7b1877Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-32a8d5bcc2b85a74a155Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-452bbd1db4fb12108bd7Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-03xr-0060090000-c0b0d4fb68cc8ede7652Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-03xr-0060090000-44d379b45665fc246c51Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0090000000-0c52a790f84a5eb190a6Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-014i-0090000000-fabbf06e73fd06941e68Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00yi-0290850000-b9c4cdaeda23f6195e6fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190300000-1dc666cd96fc2b760a46Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1290100000-84adfe1b3fe469a1cd73Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02u0-0451690000-6d33673ba45c4b2dd891Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1791420000-f60f5bcddb17587b8e43Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3980000000-e9e35d8b0c0fef1b4310Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0090040000-faef2699c3f8cb00e923Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00f0-0090910000-5126907d8e8ecaed99beSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0090000000-60b322ff74af8a765580Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000190000-5b9a8f7267b5cf79ab43Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yi-0050790000-47c087ab880d27579898Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0090010000-4e7c2ee3f7906a80ca74Spectrum
NMRNot Available
ChemSpider ID4718769
ChEMBL IDNot Available
KEGG Compound IDC04858
Pubchem Compound ID5840046
Pubchem Substance IDNot Available
ChEBI ID15932
Phenol-Explorer ID261
DrugBank IDNot Available
HMDB IDHMDB30843
CRC / DFC (Dictionary of Food Compounds) IDKQW27-E:CNR75-N
EAFUS IDNot Available
Dr. Duke IDAPIIN
BIGG IDNot Available
KNApSAcK IDC00001019
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDApiin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bradykinicDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor52425 An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.