Natamycin

Details

• Internal ID: eac85495-ce2e-4c5e-83b3-876020464193
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides
• IUPAC Name: (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
• SMILES (Canonical): 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
• SMILES (Isomeric): C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](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
• InChI Key: NCXMLFZGDNKEPB-FFPOYIOWSA-N
• Popularity: 1,882 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₇NO₁₃
• Molecular Weight: 665.70 g/mol
• Exact Mass: 665.30474055 g/mol
• Topological Polar Surface Area (TPSA): 231.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): 0.12
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• pimaricin
• 7681-93-8
• Myprozine
• Pimafucin
• Tennecetin
• Natacyn
• Natamicina
• Natamycine
• Delvocid
• Mycophyt
• Pimaracin
• Synogil
• Natamycinum
• Pimarizin
• Antibiotic A-5283
• Delvolan
• Pimaricine
• CL 12,625
• 8O0C852CPO
• INS NO.235
• INS-235
• NSC-759167
• CL 12625
• CL-12625
• DTXCID301163
• E-235
• 16-(3-Amino-3,6-didesoxy-beta-D-mannopyranosyloxy)-5,6-epoxy-8,12,14-trihydroxy-26-methyl-2,10-dioxo-1-oxacyclohexacosa-3,17,19,21,23-pentaen-13-carbonsaeure
• DTXSID6021163
• CHEBI:7488
• (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
• (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
• RefChem:56874
• DTXCID501473823
• (1R,3S,5R,7R,12R,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(22.3.1.0^(5,7))octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
• (1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)-22-(3-Amino-3,6-dideoxy-beta-D-mannopyranosyloxy)-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
• 231-683-5
• 6,11,28-Trioxatricyclo(22.3.1.05,7)octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, 22-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-
• DTXSID201015573
• MFCD00135085
• Delvopos
• Natafucin
• Natamycin(Pimaricin)
• C33H47NO13
• Tymasil
• 6,11,28-Trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, 22-[(3-amino-3,6-dideoxy-.beta.-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-
• Pimarizin [German]
• Natamycine [INN-French]
• Natamycinum [INN-Latin]
• Natamicina [INN-Spanish]
• UNII-8O0C852CPO
• Tennecetin;
• Myprozine;
• Natafucin;
• Pimafucin;
• Pimafugin;
• Mycophyt;
• Natacyn;
• Synogil;
• Natamycin [USAN:USP:INN:BAN]
• NCGC00016686-01
• (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0~5,7~]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
• 6,11,28-TRIOXATRICYCLO(22.3.1.05,7)OCTACOSA-8,14,16,18,20-PENTAENE-25-CARBOXYLIC ACID, 22-((3-AMINO-3,6-DIDEOXY-.BETA.-D-MANNOPYRANOSYL)OXY)-1,3,26-TRIHYDROXY-12-METHYL-10-OXO-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-
• CAS-7681-93-8
• EINECS 231-683-5
• Pimaricin; Natamycin
• Natamycin (Standard)
• NATAMYCIN [FCC]
• NATAMYCIN [INN]
• PIMARICIN [JAN]
• NATAMYCIN [MI]
• NATAMYCIN [USAN]
• NATAMYCIN [VANDF]
• NATAMYCIN [MART.]
• NATAMYCIN [USP-RS]
• NATAMYCIN [WHO-DD]
• SCHEMBL18140
• 0(5,7)]octacosa-8,14,16,18,20-pentaene-25-carboxylic ac
• orb1310363
• orb3025289
• NATAMYCIN [ORANGE BOOK]
• CHEMBL1200656
• HY-B0133R
• MSK2531
• NATAMYCIN [USP MONOGRAPH]
• NCXMLFZGDNKEPB-FFPOYIOWSA-N
• Pimaricin 100 |Ig/mL in Water
• (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-methyltetrahydro-2H-pyran-2-yl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.
• (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-methyltetrahydro-2H-pyran-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
• EX-A1989
• HY-B0133
• Tox21_110561
• BDBM50370755
• EBC-27421
• AKOS030485970
• 73 - Natamycin (pimaricin) in cheese
• AN26164
• CS-1909
• DB00826
• NSC 759167
• NICOTINAMIDE_ADENINE_DINUCLEOTIDE
• Stereoisomer of 22-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo(22.3.1.0(sup 5,7))octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
• NS00003340
• Natamycin, VETRANAL(TM), analytical standard
• NCGC00373238-02_C33H47NO13_Delvocid
• EN300-22411493
• F806751
• Pimaricin preparation, ~2.5%, aqueous suspension
• Q248466
• Natamycin, United States Pharmacopeia (USP) Reference Standard
• Pimaricin, from Streptomyces chattanoogensis, >=95% (HPLC)
• Natamycin, Pharmaceutical Secondary Standard; Certified Reference Material
• (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-methyl-tetrahydropyran-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
• (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-Amino-3,6-dideoxy-|A-D-mannopyranosyl)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
• (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[22.3.1.0,5,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9011	90.11%
Caco-2	-	0.8732	87.32%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Lysosomes	0.5232	52.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7991	79.91%
OATP1B3 inhibitior	+	0.9523	95.23%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7548	75.48%
P-glycoprotein inhibitior	+	0.6086	60.86%
P-glycoprotein substrate	+	0.6494	64.94%
CYP3A4 substrate	+	0.7038	70.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8667	86.67%
CYP3A4 inhibition	-	0.8632	86.32%
CYP2C9 inhibition	-	0.9154	91.54%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.7842	78.42%
CYP inhibitory promiscuity	-	0.9632	96.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4849	48.49%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.7742	77.42%
Skin corrosion	-	0.9214	92.14%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7706	77.06%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.8475	84.75%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8045	80.45%
Acute Oral Toxicity (c)	III	0.7892	78.92%
Estrogen receptor binding	+	0.7793	77.93%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5157	51.57%
Glucocorticoid receptor binding	+	0.6934	69.34%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6589	65.89%
Honey bee toxicity	-	0.6671	66.71%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.4045	40.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293232	Q16637	Survival motor neuron protein	891.3 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	1.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.89%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.46%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.57%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.24%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.98%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	93.73%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.47%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.06%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	88.20%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.81%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.64%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.33%	95.89%
CHEMBL4208	P20618	Proteasome component C5	86.94%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.57%	89.00%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	84.13%	95.52%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.53%	95.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.94%	93.56%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.83%	97.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.48%	94.42%

Plants that contains it

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Cross-Links

• PubChem: 5284447
• LOTUS: LTS0140365
• wikiData: Q248466