ContaminantDB: Fusaproliferin

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

Record Information

Version

1.0

Creation Date

2014-08-29 05:16:58 UTC

Update Date

2026-04-06 17:02:18 UTC

Accession Number

CHEM003071

Identification

Common Name

Fusaproliferin

Class

Small Molecule

Description

Fusaproliferin is a toxic metabolite originally isolated from cultures of F. proliferatum. It is a sesterterpene compound that has toxic activity against brine shrimp (Artemia salina L.), insect cells, and human B lymphocytes and has teratogenic effects on chicken embryos (1, 2).

Contaminant Sources

T3DB toxins

Contaminant Type

Carbamate
Ester
Ether
Fungal Toxin
Marine Toxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-{2,13-dihydroxy-3a,6,10,14-tetramethyl-3-oxo-3H,3ah,4H,7H,8H,11H,12H,13H,14H,15H,16H,16ah-cyclopenta[15]annulen-1-yl}propyl acetic acid	Generator
2-[(8Z,12Z)-5,17-Dihydroxy-4,8,12,15-tetramethyl-16-oxo-18-bicyclo[13.3.0]octadeca-8,12,17-trienyl]propyl acetic acid	Generator

Chemical Formula

C₂₇H₄₂O₅

Average Molecular Mass

446.619 g/mol

Monoisotopic Mass

446.303 g/mol

CAS Registry Number

Not Available

IUPAC Name

Not Available

Traditional Name

2-{2,13-dihydroxy-3a,6,10,14-tetramethyl-3-oxo-4H,7H,8H,11H,12H,13H,14H,15H,16H,16aH-cyclopenta[15]annulen-1-yl}propyl acetate

SMILES

[H]\C1=C(C)\CCC(O)C(C)CCC2C(C(C)COC(C)=O)=C(O)C(=O)C2(C)C\C([H])=C(C)/CC1

InChI Identifier

InChI=1S/C27H42O5/c1-17-8-7-9-18(2)14-15-27(6)22(12-11-19(3)23(29)13-10-17)24(25(30)26(27)31)20(4)16-32-21(5)28/h8,14,19-20,22-23,29-30H,7,9-13,15-16H2,1-6H3/b17-8-,18-14-

InChI Key

NXAIHHHELDCRMP-XDORWZGFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	0.0041 g/L	ALOGPS
logP	4.8	ALOGPS
logP	5.13	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-0.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.51 m³·mol⁻¹	ChemAxon
Polarizability	50.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00p1-0006900000-380b1b98b34db4cb2255	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00n0-1109200000-2c1bfe54e781ba953075	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0adl-3159000000-ffdf0faf8a7bfa405812	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-3001900000-59aa5b5d958b1c47abc4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4j-9005600000-95b424b57fbde40b4417	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9002100000-f61cef25c05637ede07e	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)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Fusaproliferin is a toxic metabolite originally isolated from cultures of F. proliferatum.

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

Not Available

FooDB ID

Not Available

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

6477483

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Fusaproliferin (CHEM003071)

Structure for CHEM003071: Fusaproliferin