ContaminantDB: Annoglabasin A

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 23:51:28 UTC

Update Date

2016-11-09 01:18:29 UTC

Accession Number

CHEM027618

Identification

Common Name

Annoglabasin A

Class

Small Molecule

Description

Constituent of Annona glabra (pond apple). Annoglabasin A is found in alcoholic beverages and fruits.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Methyl ent-16a-acetoxy-19-oxo-17-kauranoate	HMDB
Methyl 14-(acetyloxy)-5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylic acid	Generator

Chemical Formula

C₂₃H₃₄O₅

Average Molecular Mass

390.513 g/mol

Monoisotopic Mass

390.241 g/mol

CAS Registry Number

205312-85-2

IUPAC Name

methyl 14-(acetyloxy)-5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylate

Traditional Name

methyl 14-(acetyloxy)-5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carboxylate

SMILES

COC(=O)C1(CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3)OC(C)=O

InChI Identifier

InChI=1S/C23H34O5/c1-15(25)28-23(19(26)27-4)13-22-11-8-17-20(2,14-24)9-5-10-21(17,3)18(22)7-6-16(23)12-22/h14,16-18H,5-13H2,1-4H3

InChI Key

GBAYHCBQSSWKTG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00053 g/L	ALOGPS
logP	3.15	ALOGPS
logP	3.69	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	103.75 m³·mol⁻¹	ChemAxon
Polarizability	43.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0535-3098000000-37d3409c9c9e398a6c33	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0019000000-350bfe7878f2b82daec0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000w-1159000000-beed1fb8e851b80dfae6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-2692000000-74e0363e88e1fe8354cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1009000000-8a0195cd11b6875c2e39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4s-4019000000-e768cb1bcdedf3684fa8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-9031000000-a17f52a873e831848248	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0nmi-0009000000-9fd5e90654ef0152d4fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-114i-0849000000-31b33e4479cf41b0aa14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06yd-3941000000-099162ac37757ed447af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-4387b01c6ff0b13fcaea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0adi-5059000000-71a6aac12ba7bc286b2f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9020000000-7a6e2a9a0597e52aca95	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0033400

FooDB ID

FDB011434

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

73657053

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.

2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.

3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.

4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.

5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

6. The lipid handbook with CD-ROM

Annoglabasin A (CHEM027618)

Structure for CHEM027618: Annoglabasin A