ContaminantDB: Aurovertin D

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

Record Information

Version

1.0

Creation Date

2010-05-12 17:31:41 UTC

Update Date

2026-04-06 13:15:08 UTC

Accession Number

CHEM002719

Identification

Common Name

Aurovertin D

Class

Small Molecule

Description

Aurovertin D is an exogenous solid with the formula C25H32O9 and an average molecular weight of 476.52 g/mol. Aurovertin D belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. It acts as a mixed, noncompetitive inhibitor of both ATP synthesis and hydrolysis by targeting the mitochondrial ATP synthase F(1) complex subunit beta (ATP5F1B). By binding to beta-subunits in the F1 catalytic sector, it inhibits the proton-pumping F1F0-ATP synthase, which is responsible for the terminal step of oxidative phosphorylation. Aurovertins are believed to bind with varying affinity to two of the three beta subunits at sites in a cleft between the C-terminal and nucleotide-binding domains.

Contaminant Sources

T3DB toxins

Contaminant Type

Ester
Ether
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxy-7-(1-hydroxyethyl)-3-[(1Z,3E,5E)-6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₂O₉

Average Molecular Mass

476.522 g/mol

Monoisotopic Mass

476.205 g/mol

CAS Registry Number

65256-31-7

IUPAC Name

Not Available

Traditional Name

4-hydroxy-7-(1-hydroxyethyl)-3-[(1Z,3E,5E)-6-(4-methoxy-3-methyl-6-oxopyran-2-yl)hexa-1,3,5-trien-1-yl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl acetate

SMILES

[H]/C(=C(/[H])\C(\[H])=C(/[H])C1=C(C)C(OC)=CC(=O)O1)/C(/[H])=C(/[H])C1OC2(C)C(OC(C)(C2OC(C)=O)C1O)C(C)O

InChI Identifier

InChI=1S/C25H32O9/c1-14-17(32-20(28)13-19(14)30-6)11-9-7-8-10-12-18-21(29)24(4)23(31-16(3)27)25(5,33-18)22(34-24)15(2)26/h7-13,15,18,21-23,26,29H,1-6H3/b8-7+,11-9+,12-10-

InChI Key

UKPVUEBWITXZRF-CDIKDJIESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Pyranone
Dioxepane
Alkyl aryl ether
1,4-dioxepane
Pyran
Oxane
Heteroaromatic compound
Vinylogous ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.04 g/L	ALOGPS
logP	3.4	ALOGPS
logP	1.4	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.9	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	120.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	126.94 m³·mol⁻¹	ChemAxon
Polarizability	50.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05r0-0000900000-96dd09a16ab013275931	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ldi-0164900000-817c4db2203b9e1d0acb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btc-9061100000-80e8de3470aca3c73a21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-1010900000-5a89afeb6d38734ae5c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-7210900000-75f89f749fd7af51b387	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9101000000-7e456ac079cfa1d02997	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (5)

Mechanism of Toxicity

Aurovertins are a mixed, noncompetitive inhibitors of both ATP hydrolysis and synthesis. They do this by inhibiting the proton-pumping F1F0-ATP synthase by binding to beta-subunits in its F1 catalytic sector. F1F0-ATP synthase is responsible for the terminal step of oxidative phosphorylation. Each ATP synthase complex has three beta subunits, and aurovertins are believed to bind with varying affinity to two subunits on sites in a cleft between the nucleotide-binding and C-terminal domains, thus preventing closure of the catalytic interfaces necessary for the cyclic interconversion of catalytic sites. (2, 3, 4)

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

Aurovertin D is a mycotoxin and antibiotic produced by the fungus Calcarisporium arbuscula. (1)

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

Not Available

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

Aurovertin D (CHEM002719)

Structure for CHEM002719: Aurovertin D