ContaminantDB: Luteoskyrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (26)XML

Record Information

Version

1.0

Creation Date

2010-05-21 14:46:10 UTC

Update Date

2026-04-03 17:45:28 UTC

Accession Number

CHEM002735

Identification

Common Name

Luteoskyrin

Class

Small Molecule

Description

Luteoskyrin is a mycotoxin produced by the fungus Penicillium islandicum. It is known to be a storage mold contaminant of rice and has been shown to be hepatotoxic and hepatocarcinogenic. (3, 4)

Contaminant Sources

IARC Carcinogens Group 3
T3DB toxins

Contaminant Type

Ester
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₂

Average Molecular Mass

574.489 g/mol

Monoisotopic Mass

574.111 g/mol

CAS Registry Number

21884-44-6

IUPAC Name

5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.0²,¹¹.0²,¹⁵.0⁴,⁹.0¹³,¹⁷.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone

Traditional Name

5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.0²,¹¹.0²,¹⁵.0⁴,⁹.0¹³,¹⁷.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone

SMILES

CC1=CC(O)=C2C(O)=C3C(=O)C4C(O)C5C6C(O)C(C(=O)C7=C(O)C8=C(O)C=C(C)C(O)=C8C(=O)C467)C35C(=O)C2=C1O

InChI Identifier

InChI=1S/C30H22O12/c1-5-3-7(31)9-11(19(5)33)27(41)29-13-14-24(38)17(29)26(40)16-22(36)10-8(32)4-6(2)20(34)12(10)28(42)30(14,16)18(23(13)37)25(39)15(29)21(9)35/h3-4,13-14,17-18,23-24,31-38H,1-2H3

InChI Key

FAZDYVMEXQHRLI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

1-naphthol
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Cyclic alcohol
Vinylogous acid
Ketone
Secondary alcohol
Enol
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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

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	1.84 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.11	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	5.57	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	230.12 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	143.69 m³·mol⁻¹	ChemAxon
Polarizability	54.88 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_17) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_18) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_19) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_20) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a70-0000090000-2802b1bfb3a08a9f9f92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pdr-0401690000-950a77ce1902c5fe5df9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0204590000-bfc526ba9b4e7659962d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000090000-2adda3d26a159a3cf30f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-0000090000-8a1008a036e816f04aca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-6502590000-e7ca8c894d5cdc2fbcfb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000090000-8c8d92232af9500789ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000090000-20978721d0c4f47f2169	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ba-1200590000-171c06e8dc09c6a3c12d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000090000-2f6d4dc81e5e1f72f718	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0000090000-8d09ffbe7956495fbdc4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fr-0200590000-969c4740eb3e9fb1bf8f	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (7)

Mechanism of Toxicity

Luteoskyrin is hepatotoxic. It is thought that this is a result of its metabolic reduction to the semiquinone radical catalyzed by NADPH-dependent cytochrome reductases in the liver, leading to the generation of active oxygen species in redox systems. This causes the induction of lipid peroxidation, hepatocellular membrane damage, and elevation of serum transaminase activities, resultin in liver injuries. Luteoskyrin is also hepatocarcinogenic, possibly a result of its ability to induce DNA fragmentation. It is able to bind to DNA, forming chelate-complexes with nucleic acids and select metal ions. Luteoskyrin inhibits the replication, transcription and repair of DNA, which is at least partially because it inhibits RNA polymerase and ribonuclease H. (1, 2, 4, 5, 6)

Metabolism

Luteoskyrin accumulates selectively in the liver, with minor distribution to the serum and kidneys. In the liver it is reduced to its semiquinone radical by NADPH-dependent cytochrome reductases. (4, 5)

Toxicity Values

Not Available

Lethal Dose

145 mg/kg subcutaneously and 221 mg/kg orally in mice. (3)

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (8)

Uses/Sources

Luteoskyrin is a mycotoxin produced by the fungus Penicillium islandicum. It is known to be a storage mold contaminant of rice. (3)

Minimum Risk Level

Not Available

Health Effects

Luteoskyrin is hepatotoxic and hepatocarcinogenic, causing hepatic disorders such as liver cirrhosis and liver tumors. (3, 4)

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0254226

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

Luteoskyrin

Chemspider ID

28613

ChEBI ID

Not Available

PubChem Compound ID

30840

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.

Luteoskyrin (CHEM002735)

Structure for CHEM002735: Luteoskyrin