Showing Compound Anonaine (FDB002193)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:16 UTC

Update date

2020-02-24 19:10:27 UTC

Primary ID

FDB002193

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Anonaine

Description

Anonaine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Anonaine is found, on average, in the highest concentration within custard apples (Annona reticulata). Anonaine has also been detected, but not quantified in, several different foods, such as sugar apples (Annona squamosa), cherimoyas (Annona cherimola), black tea, herbal tea, and fruits. This could make anonaine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Anonaine.

CAS Number

1862-41-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(-)-Annonaine	HMDB
1,2-Methylenedioxynoraporphine	HMDB
Anonain	HMDB
(-)-annonaine	biospider
Anonaine	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.034 g/L	ALOGPS
logP	2.22	ALOGPS
logP	2.94	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	9.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	30.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.5 m³·mol⁻¹	ChemAxon
Polarizability	29.11 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H15NO2

IUPAC name

3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene

InChI Identifier

InChI=1S/C17H15NO2/c1-2-4-12-10(3-1)7-13-15-11(5-6-18-13)8-14-17(16(12)15)20-9-19-14/h1-4,8,13,18H,5-7,9H2

InChI Key

VZTUKBKUWSHDFM-UHFFFAOYSA-N

Isomeric SMILES

C1OC2=C(O1)C1=C3C(CC4=CC=CC=C14)NCCC3=C2

Average Molecular Weight

265.3065

Monoisotopic Molecular Weight

265.110278729

Classification

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Aralkylamine
Benzenoid
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary aliphatic amine
Acetal
Secondary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

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 76.96%; H 5.70%; N 5.28%; O 12.06%	DFC
Melting Point	Mp 122-123°	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]31D -68 (c, 0.77 in EtOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Anonaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00kr-0290000000-eef0189b19c023e62512	Spectrum
Predicted GC-MS	Anonaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-e9a2afab256159ae2699	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0090000000-f7ca3522e83754962ac6	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00pl-1980000000-a0014a6236a9bf51d76e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-74185903329bd522c04a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0090000000-7de3784592381bb7a862	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014m-1490000000-2f75c30aa943164353af	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-4ceb63c2dd5efc77f44c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0090000000-4ceb63c2dd5efc77f44c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ds-0190000000-9a10adc3866934e256bc	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-f67efedff389fe87473b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0090000000-e7468aac66a5ed55954f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000t-0090000000-d457525b01f969160b5d	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

2704037

ChEMBL ID

Not Available

KEGG Compound ID

C09339

Pubchem Compound ID

3462225

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30348

CRC / DFC (Dictionary of Food Compounds) ID

CFF87-G:CGV80-I

EAFUS ID

Not Available

Dr. Duke ID

ANONAINE

BIGG ID

Not Available

KNApSAcK ID

C00027281

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

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Knapsack: C00001807

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
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Candidicide		An agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.	DUKE
Cytotoxic	52209	An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.	DUKE
Dopamine-adenylate-cyclase inhibitor	23924	An agent that blocks dopamine's stimulation of adenylate cyclase, reducing cyclic AMP production. It has therapeutic applications in treating schizophrenia, bipolar disorder, and other psychiatric conditions, as well as key medical uses in managing dopamine-related disorders and movement disorders.	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Hypotensive		An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.	DUKE
Insecticide	24852	An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.	DUKE
Mycoplasma		An agent that kills bacteria of the genus Mycoplasma, playing a role in treating mycoplasma infections. Therapeutically, it is used to target and eliminate these bacteria, commonly used in managing respiratory and urogenital tract infections.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE