Showing Compound Natamycin (FDB002337)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:20 UTC

Update date

2018-05-28 22:40:07 UTC

Primary ID

FDB002337

Secondary Accession Numbers

FDB012915

Chemical Information

FooDB Name

Natamycin

Description

Primarily used as a surface treatment to prevent growth of yeasts and moulds, especies on cheese. Permitted agent in USA for surface treatment of cheeses as mould-inhibitor. No reported allergic reactions and it has GRAS status Natamycin (INN), also known as pimaricin, is a naturally occurring antifungal agent produced during fermentation by the bacterium Streptomyces natalensis, commonly found in soil. Natamycin has a very low solubility in water, due to the amphiphilic nature of the molecule. However, natamycin is effective at very low levels. Most Molds have an MIC (Minimum inhibitory concentration) of <10ppm. Natamycin is classified as a macrolide polyene antifungal and, as a drug, is used to treat fungal keratitis. It is especially effective against Aspergillus and Fusarium corneal infections. Other common members of the polyene macrolide antifungal family are Amphotericin B, Nystatin, and Filipin.; Natamycin is an antifungal drug for topical ophthalmic administration. It is a tetraene polyene antibiotic derived from Streptomyces natalensis. It possesses in vitro activity against a variety of yeast and filamentous fungi, including Candida, Aspergillus, Cephalosporium, Fusarium and Penicillium. Although the activity against fungi is dose-related, natamycin is predominantly fungicidal. Natamycin is not effective in vitro against gram-positive or gram-negative bacteria. Topical administration appears to produce effective concentrations of natamycin within the corneal stroma but not in intraocular fluid.

CAS Number

7681-93-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Showing 1 to 10 of 29 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	-3.5	ALOGPS
logP	-1.7	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	230.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	169.88 m³·mol⁻¹	ChemAxon
Polarizability	68.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C33H47NO13

IUPAC name

(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0⁵,⁷]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

InChI Identifier

InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32?,33-/m1/s1

InChI Key

NCXMLFZGDNKEPB-BQGNJOPGSA-N

Isomeric SMILES

C[C@H]1OC(O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)[C@@H](O)[C@@H](N)[C@@H]1O

Average Molecular Weight

665.7252

Monoisotopic Molecular Weight

665.304740595

Classification

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
Macrolide
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Hydroxy acid
Monosaccharide
Dicarboxylic acid or derivatives
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Hemiacetal
Secondary alcohol
Carboxylic acid ester
Amino acid
Amino acid or derivatives
1,2-aminoalcohol
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Dialkyl ether
Organoheterocyclic compound
Oxirane
Ether
Polyol
Alcohol
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Carbonyl group
Organonitrogen compound
Primary aliphatic amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

antibiotic antifungal drug (CHEBI:7488 )
macrolide (CHEBI:7488 )
Antibiotic fungicides (C08073 )

Ontology

Disposition

Source:

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Drug

Pharmaceutical industry:

Antimycotic

Household products:

Antifungal

Antimicrobial agent:

Antibacterial

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	4.1 mg/mL at 21 oC	TOMLIN,C (1994)
Isoelectric point	Not Available
Mass Composition	C 59.54%; H 7.12%; N 2.10%; O 31.24%	DFC
Melting Point	Mp 200°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Natamycin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002b-9200015000-f595a5ec647350aa5e44	Spectrum
Predicted GC-MS	Natamycin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Natamycin, TMS_2_17, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ul1-0000159000-db7c73a2c6e943055873	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0300292000-e96b0296247cf041eb27	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-0509350000-4c2c7b4ac6bdbd8f7641	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0w9a-2000139000-12a04d582d7eb949cc7f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fr2-0000192000-dbfe316890501907db18	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-9202420000-e05573710a8f58a421d2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxs-0000059000-3e978a72825660654a87	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000094000-2dfd35d7e9ce10554843	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fl1-8500193000-9281f959f7d6a0dfa98b	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0imi-0200219000-3319c9ecec161550e327	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ik9-2000395000-60d0b7e3401384f6ddb3	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1000390000-a1a7a8f92824688e8cf0	2021-10-11	View Spectrum