ContaminantDB: Ustiloxin A

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

Record Information

Version

1.0

Creation Date

2016-05-26 03:50:14 UTC

Update Date

2016-11-09 01:20:49 UTC

Accession Number

CHEM032961

Identification

Common Name

Ustiloxin A

Class

Small Molecule

Description

Ustiloxin A is found in cereals and cereal products. Ustiloxin A is isolated from the false smut balls caused by Ustilaginoidea virens on rice.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-5-({4-[(carboxymethyl)-C-hydroxycarbonimidoyl]-3-ethyl-6,9,11,15-tetrahydroxy-3-methyl-10-(methylamino)-7-(propan-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-13-yl}sulfinyl)-4-hydroxypentanoate	HMDB
2-Amino-5-({4-[(carboxymethyl)-C-hydroxycarbonimidoyl]-3-ethyl-6,9,11,15-tetrahydroxy-3-methyl-10-(methylamino)-7-(propan-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-13-yl}sulphinyl)-4-hydroxypentanoate	HMDB
2-Amino-5-({4-[(carboxymethyl)-C-hydroxycarbonimidoyl]-3-ethyl-6,9,11,15-tetrahydroxy-3-methyl-10-(methylamino)-7-(propan-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-13-yl}sulphinyl)-4-hydroxypentanoic acid	HMDB
Ustiloxin a	MeSH

Chemical Formula

C₂₈H₄₃N₅O₁₂S

Average Molecular Mass

673.732 g/mol

Monoisotopic Mass

673.263 g/mol

CAS Registry Number

141044-51-1

IUPAC Name

2-amino-5-({4-[(carboxymethyl)carbamoyl]-3-ethyl-11,15-dihydroxy-3-methyl-10-(methylamino)-6,9-dioxo-7-(propan-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-13-yl}sulfinyl)-4-hydroxypentanoic acid

Traditional Name

2-amino-5-[4-(carboxymethylcarbamoyl)-3-ethyl-11,15-dihydroxy-7-isopropyl-3-methyl-10-(methylamino)-6,9-dioxo-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-13-ylsulfinyl]-4-hydroxypentanoic acid

SMILES

CCC1(C)OC2=CC(C(O)C(NC)C(=O)NC(C(C)C)C(=O)NC1C(=O)NCC(O)=O)=C(C=C2O)S(=O)CC(O)CC(N)C(O)=O

InChI Identifier

InChI=1S/C28H43N5O12S/c1-6-28(4)23(26(41)31-10-19(36)37)33-24(39)20(12(2)3)32-25(40)21(30-5)22(38)14-8-17(45-28)16(35)9-18(14)46(44)11-13(34)7-15(29)27(42)43/h8-9,12-13,15,20-23,30,34-35,38H,6-7,10-11,29H2,1-5H3,(H,31,41)(H,32,40)(H,33,39)(H,36,37)(H,42,43)

InChI Key

QRLBQXQEGMBXFM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Macrolactam
Alpha-amino acid amide
Alpha-amino acid
Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aralkylamine
Benzenoid
Dicarboxylic acid or derivatives
1,3-aminoalcohol
Amino acid
Sulfoxide
Secondary carboxylic acid amide
Lactam
Secondary alcohol
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Carboxylic acid
Organoheterocyclic compound
Secondary aliphatic amine
Sulfinyl compound
Ether
Secondary amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Amine
Organic nitrogen compound
Primary amine
Primary aliphatic amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.01 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-8	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.05	ChemAxon
pKa (Strongest Basic)	8.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	286.94 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	161.85 m³·mol⁻¹	ChemAxon
Polarizability	65.61 Å³	ChemAxon
Number of Rings	2	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 (Non-derivatized) - 70eV, Positive	splash10-0596-6100049000-b54d36fb11a038ce5b15	Spectrum
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_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-022c-3233169000-2329039a0411a98743fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-3100292000-a8e7f3bb3b28ceeab6e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-8942000000-fea6765fb2de2024daca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-3200059000-d78c5ea9414517fa6e90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kg6-8201961000-c24275cccf40a8602ce5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0076-9001530000-b728acafb3626cbc8bb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0c29-1000019000-d3c28640ac1318294538	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9300023000-9aadbfee69793ced3cce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9505300000-1c97a0136750a5ddf337	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0200179000-249566cb41aa488dcc12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0541-0100097000-79e62a3299515fea5380	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-9500510000-ed6568adcdaf8e05858a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	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

HMDB0039640

FooDB ID

FDB019268

Phenol Explorer ID

Not Available

KNApSAcK ID

C00016646

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

3678075

ChEBI ID

Not Available

PubChem Compound ID

4480102

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

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

Ustiloxin A (CHEM032961)

Structure for CHEM032961: Ustiloxin A