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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:22 UTC
Update Date2022-03-07 02:52:43 UTC
HMDB IDHMDB0030843
Secondary Accession Numbers
  • HMDB30843
Metabolite Identification
Common 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 peppers (Capsicum annuum), yellow bell peppers (Capsicum annuum), green bell peppers (Capsicum annuum), pepper (c. frutescens), and orange bell peppers (Capsicum annuum). 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.
Structure
Thumb
Synonyms
ValueSource
7-(2-Apiosylglucosyl)apigeninHMDB
Apigenin 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside]HMDB
Apigenin-7-apioglucosideHMDB
ApiosideHMDB
ApiinMeSH
6''-AcetylapiinMeSH
Chemical FormulaC26H28O14
Average Molecular Weight564.4921
Monoisotopic Molecular Weight564.147905604
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
Traditional 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)chromen-4-one
CAS Registry Number26544-34-3
SMILES
OCC1OC(OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)C(OC2OCC(O)(CO)C2O)C(O)C1O
InChI Identifier
InChI=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
Chemical Taxonomy
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point236 - 237 °CNot Available
Boiling Point942.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility3889 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.720 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 IDFDB002801
KNApSAcK IDC00001019
Chemspider ID4718769
KEGG Compound IDC04858
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkApiin
METLIN IDNot Available
PubChem Compound5840046
PDB IDNot Available
ChEBI ID15932
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1588401
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 sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Apiin → ({5-[(4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)oxy]-3,4-dihydroxyoxolan-3-yl}methoxy)sulfonic aciddetails
Apiin → {2-[(4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)oxy]-4-hydroxy-4-(hydroxymethyl)oxolan-3-yl}oxidanesulfonic aciddetails
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
Apiin → 6-(4-{7-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-5-hydroxy-4-oxo-4H-chromen-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Apiin → 6-({7-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails