ContaminantDB: Candicidin

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

Record Information

Version

1.0

Creation Date

2016-05-25 18:25:34 UTC

Update Date

2016-11-09 01:17:27 UTC

Accession Number

CHEM022249

Identification

Common Name

Candicidin

Class

Small Molecule

Description

Candicidin is only found in individuals that have used or taken this drug. It is an antibiotic obtained from a streptomyces (Streptomyces griseus) and active against some fungi of the genus Candida (C. albicans). Candicidin is administered intravaginally in the treatment of vulvovaginal candidiasis.Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of Candicidin. Candicidin binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death. There is some evidence that the binding site in the cell wall may be to fatty acids or fatty acid esters and that this binding capacity must be satisfied before candicidin can bring about its lethal effect by binding to sterol in the cell membrane.

Contaminant Sources

HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
33-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-17-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-1,3,5,7,37-pentahydroxy-18-methyl-9,13,15-trioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate	HMDB

Chemical Formula

C₅₉H₈₄N₂O₁₈

Average Molecular Mass

1109.301 g/mol

Monoisotopic Mass

1108.572 g/mol

CAS Registry Number

1403-17-4

IUPAC Name

(19Z,21Z,23Z,25Z,27Z,29Z,31Z)-33-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-17-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-1,3,5,7,37-pentahydroxy-18-methyl-9,13,15-trioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid

Traditional Name

candicidin

SMILES

CC(CC(C)C1OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)CC2(O)CC(O)C(C(CC(OC3O[C@H](C)[C@@H](O)[C@H](N)[C@@H]3O)\C=C/C=C\C=C/C=C\C=C/C=C\C=C/C1C)O2)C(O)=O)C(O)CC(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C59H84N2O18/c1-35-18-15-13-11-9-7-5-6-8-10-12-14-16-21-46(77-58-55(72)53(61)54(71)38(4)76-58)31-50-52(57(73)74)49(69)34-59(75,79-50)33-45(66)29-44(65)28-43(64)27-41(62)19-17-20-42(63)30-51(70)78-56(35)37(3)26-36(2)47(67)32-48(68)39-22-24-40(60)25-23-39/h5-16,18,21-25,35-38,43-47,49-50,52-56,58,64-67,69,71-72,75H,17,19-20,26-34,60-61H2,1-4H3,(H,73,74)/b6-5-,9-7-,10-8-,13-11-,14-12-,18-15-,21-16-/t35?,36?,37?,38-,43?,44?,45?,46?,47?,49?,50?,52?,53+,54-,55+,56?,58?,59?/m1/s1

InChI Key

YKSVGLFNJPQDJE-WDANKXQLSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Alkyl-phenylketone
Macrolide
Butyrophenone
Glycosyl compound
O-glycosyl compound
Phenylketone
Benzoyl
Aryl ketone
Aryl alkyl ketone
Aniline or substituted anilines
Beta-hydroxy acid
Beta-hydroxy ketone
Benzenoid
1,3-dicarbonyl compound
Dicarboxylic acid or derivatives
Hydroxy acid
Monocyclic benzene moiety
Oxane
Monosaccharide
Cyclic ketone
Carboxylic acid ester
Secondary alcohol
1,2-aminoalcohol
Hemiacetal
Ketone
Amino acid or derivatives
Amino acid
Lactone
Carboxylic acid derivative
Acetal
Carboxylic acid
Polyol
Organoheterocyclic compound
Oxacycle
Primary amine
Organopnictogen compound
Carbonyl group
Organic oxide
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organonitrogen compound
Amine
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	0.0093 g/L	ALOGPS
logP	-0.94	ALOGPS
logP	0.93	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	356.38 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	300.5 m³·mol⁻¹	ChemAxon
Polarizability	119.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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	splash10-00di-9100000004-36afc554bc7070a9ba35	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dj-3400000109-af42c14e1f45a3e8049e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-4500000429-327b513f8910b1791e67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01pa-9200000002-d31a58f2670ba9c90a8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-029j-7000000009-5a69d6b13316c2cc9bf7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01po-2200000049-988c3c28c2903a02dba3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9300000003-e48722f8e75175fb6467	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-6300000109-f0b58d45d4655938283d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01c4-9200000104-21e178ec8acbfbc86dea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0005-8200000009-80febef103198d9f0c54	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dv-9100000006-b7c2ae34669c4c2ce312	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-4100000009-b7697f4570936b9e6f16	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

HMDB0015283

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

Candicidin

Chemspider ID

10128184

ChEBI ID

Not Available

PubChem Compound ID

152743271

Kegg Compound ID

C06690

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Candicidin (CHEM022249)

Structure for CHEM022249: Candicidin