Showing Compound Apiin (FDB002801)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:31 UTC

Update date

2020-02-24 19:10:38 UTC

Primary ID

FDB002801

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Apiin

Description

Apiin 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 Number

26544-34-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
7-(2-Apiosylglucosyl)apigenin	HMDB
Apigenin 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside]	HMDB
Apigenin-7-apioglucoside	HMDB
Apioside	HMDB
Apiin	MeSH
6''-Acetylapiin	MeSH

Predicted Properties

Property	Value	Source
Water Solubility	1.53 g/L	ALOGPS
logP	-0.17	ALOGPS
logP	-0.84	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.31	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	131.73 m³·mol⁻¹	ChemAxon
Polarizability	55.4 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C26H28O14

IUPAC name

7-[(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 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 Key

NTDLXWMIWOECHG-UHFFFAOYSA-N

Isomeric 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

Average Molecular Weight

564.4921

Monoisotopic Molecular Weight

564.147905604

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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homopolycyclic compounds

External Descriptors

a secondary metabolite (CPD-12209 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 55.32%; H 5.00%; O 39.68%	DFC
Melting Point	Mp 236-237°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -130 (c, 0.12 in MeOH)	DFC
Spectroscopic UV Data	342 (e 19950) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Apiin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-007k-7230390000-be49fba592c5fd103da4	Spectrum
Predicted GC-MS	Apiin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9201006000-59afb33788ee043a12c6	Spectrum
Predicted GC-MS	Apiin, "Apiin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiin, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-03di-0000090000-a04baa45f6225c583e5a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-03xr-0070090000-8047ba073b20f04775e5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-03di-0010090000-3283a550fcfc4f7b1877	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-32a8d5bcc2b85a74a155	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-452bbd1db4fb12108bd7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-03xr-0060090000-c0b0d4fb68cc8ede7652	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-03xr-0060090000-44d379b45665fc246c51	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0090000000-0c52a790f84a5eb190a6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-014i-0090000000-fabbf06e73fd06941e68	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00yi-0290850000-b9c4cdaeda23f6195e6f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0190300000-1dc666cd96fc2b760a46	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1290100000-84adfe1b3fe469a1cd73	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02u0-0451690000-6d33673ba45c4b2dd891	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1791420000-f60f5bcddb17587b8e43	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3980000000-e9e35d8b0c0fef1b4310	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-0090040000-faef2699c3f8cb00e923	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00f0-0090910000-5126907d8e8ecaed99be	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0090000000-60b322ff74af8a765580	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000190000-5b9a8f7267b5cf79ab43	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03yi-0050790000-47c087ab880d27579898	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0090010000-4e7c2ee3f7906a80ca74	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4718769

ChEMBL ID

Not Available

KEGG Compound ID

C04858

Pubchem Compound ID

5840046

Pubchem Substance ID

Not Available

ChEBI ID

15932

Phenol-Explorer ID

261

DrugBank ID

Not Available

HMDB ID

HMDB30843

CRC / DFC (Dictionary of Food Compounds) ID

KQW27-E:CNR75-N

EAFUS ID

Not Available

Dr. Duke ID

APIIN

BIGG ID

Not Available

KNApSAcK ID

C00001019

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Apiin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Anti-arrhythmic	38070	An agent that regulates heart rhythm, correcting irregular heartbeat patterns. Therapeutically, it restores normal cardiac function, commonly used to manage arrhythmias, prevent sudden cardiac death, and treat conditions like atrial fibrillation and ventricular tachycardia.	DUKE
Anti bradykinic		An agent that inhibits the action of bradykinin, a peptide causing blood vessels to dilate and leading to increased permeability, pain, and inflammation. Therapeutically, anti-bradykinics are used to treat conditions like hereditary angioedema, reducing swelling and pain, and may also have applications in managing other inflammatory disorders.	DUKE
Anti-spasmodic	52217	An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.	DUKE
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor	52425	An agent that blocks the activity of exo-alpha-sialidase, an enzyme that breaks down sialic acid. It has therapeutic applications in treating influenza and other viral infections, and key medical uses include reducing viral replication and alleviating symptoms.	CHEBI