Pimaricin
Cyclic product of the PKS last thioesterase module is then substrate of PimK for transfer of the sugar moiety to the aglycone of pimaricin. Then PimD Cytochrome P-450 monooxygenase formation of the epoxy ring. Natamycin is a polyene amphoteric macrolide antibiotic with antifungal properties. Natamycin exerts its antifungal effects by binding to sterols in the fungal cell membrane thereby increasing membrane permeability. This leads to a leakage and loss of essential cellular constituents. Following ocular application, natamycin is retained in the conjunctival fornices and attains effective concentrations within the corneal stroma where it exerts its effect.
General
Type : Natural, Macrolide, Polyketide, Antibiotic
Chemical_Nomenclature : (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(2R,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
Canonical SMILES : CC1CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC3C(O3)C=CC(=O)O1)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O
InChI : 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
InChIKey : NCXMLFZGDNKEPB-FFPOYIOWSA-N
Other name(s) : Natamycin || Mycophyt || Synogil || Tennecetin || Delvocid
MW : 665.7
Formula : C33H47O13N\
CAS_number : 7681-93-8
PubChem : 5284447
UniChem : NCXMLFZGDNKEPB-FFPOYIOWSA-N
Target
Structures : No structure
Families : Thioesterase
References (2)
| Title : Structural and Mechanistic Insights into Chain Release of the Polyene PKS Thioesterase Domain - Zhou_2022_ACS.Catal_12_762 |
| Author(s) : Zhou Y , Tao W , Qi Z , Wei J , Shi T , Kang Q , Zheng J , Zhao Y , Bai L |
| Ref : ACS Catal , 12 :762 , 2022 |
| Abstract : |
| PubMedSearch : Zhou_2022_ACS.Catal_12_762 |
| PubMedID: |
| Gene_locus related to this paper: 9actn-f1cla7 |
| Title : A complex multienzyme system encoded by five polyketide synthase genes is involved in the biosynthesis of the 26-membered polyene macrolide pimaricin in Streptomyces natalensis - Aparicio_2000_Chem.Biol_7_895 |
| Author(s) : Aparicio JF , Fouces R , Mendes MV , Olivera N , Martin JF |
| Ref : Chemical Biology , 7 :895 , 2000 |
| Abstract : |
| PubMedSearch : Aparicio_2000_Chem.Biol_7_895 |
| PubMedID: 11094342 |
| Gene_locus related to this paper: strna-PIMI , strna-PIMS4 |