ContaminantDB: Rugulosin

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

Record Information

Version

1.0

Creation Date

2014-08-29 05:06:53 UTC

Update Date

2026-05-21 02:15:02 UTC

Accession Number

CHEM003051

Identification

Common Name

Rugulosin

Class

Small Molecule

Description

Rugulosin is an intense yellow pigment produced by some fungal species of Penicillium, Aspergillus and the fungal symbiotants of some lichens. Rugulosin shows antibacterial and insecticidal activity and has found application as a bioinsecticide, notably as the active secondary metabolite in endophytic fungi of seedlings. Rugulosin (+ form) is an inhibitor of RNA Polymerase and RNase. (1, 2).

Contaminant Sources

IARC Carcinogens Group 3
T3DB toxins

Contaminant Type

Ester
Fungal Toxin
Insecticide
Mycotoxin
Natural Compound
Organic Compound
PFAS
Pesticide

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₀

Average Molecular Mass

542.490 g/mol

Monoisotopic Mass

542.121 g/mol

CAS Registry Number

23537-16-8

IUPAC Name

Not Available

Traditional Name

8,12,14,23,27,28-hexahydroxy-6,21-dimethyloctacyclo[14.11.1.0²,¹¹.0²,¹⁵.0⁴,⁹.0¹³,¹⁷.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-4(9),5,7,11,19(24),20,22,26-octaene-3,10,18,25-tetrone

SMILES

CC1=CC2=C(C(O)=C1)C(=O)C1=C(O)C3C(O)C4C5C(O)C(C(O)=C6C(=O)C7=C(C=C(C)C=C7O)C(=O)C356)C14C2=O

InChI Identifier

InChI=1S/C30H22O10/c1-7-3-9-13(11(31)5-7)21(33)17-25(37)20-23(35)15-16-24(36)19(29(15,17)27(9)39)26(38)18-22(34)14-10(28(40)30(16,18)20)4-8(2)6-12(14)32/h3-6,15-16,19-20,23-24,31-32,35-38H,1-2H3

InChI Key

OYNIPTDPTUSUAY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Naphthalene
Tetralin
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclic alcohol
Vinylogous acid
Ketone
Secondary alcohol
Enol
Polyol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:80712 )
Mycotoxins (C16764 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Microsome
Mitochondrion

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Oxidative phosphorylation	Not Available	map00190
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	0.51 g/L	ALOGPS
logP	1.95	ALOGPS
logP	0.89	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	189.66 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	140.23 m³·mol⁻¹	ChemAxon
Polarizability	53.1 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	0	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	splash10-056u-0000090000-bfddb5ecc0370abd2c0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a73-0202290000-f75aa744ef8cbeef005f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0306190000-29007c324c9c0b6622e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000090000-141f6169daa7d2c93742	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0000090000-ea73d3213722304e300e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2903480000-34c4d7b847da7635de51	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)

3, not classifiable as to its carcinogenicity to humans. (3)

Uses/Sources

This is a natural compound that is used as a pesticide.

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

C00018763

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

80712

PubChem Compound ID

Not Available

Kegg Compound ID

C16764

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Rugulosin (CHEM003051)

Structure for CHEM003051: Rugulosin