BGC0000834

General information about the BGC

MIBiG accession	BGC0000834
Short description	cathomycin biosynthetic gene cluster from Streptomyces niveus
Status	Quality: questionable The quality level of this entry. Status: active The status of this entry. Completeness: complete Whether the entry covers everything needed for the pathway producing the compound(s)
Biosynthetic class(es)	saccharide (hybrid/tailoring) other (aminocoumarin)
Loci	AF170880.4 4859 - 28076 via Knock-out studies, Enzymatic assays, Heterologous expression
Compounds	cathomycin
Species	Streptomyces niveus [taxonomy]
References	[1] Identification of the novobiocin biosynthetic gene cluster of Streptomyces spheroides NCIB 11891. Steffensky M et al., Antimicrob Agents Chemother (2000) PMID:10770754 [2] Cloning, overexpression, and purification of novobiocic acid synthetase from Streptomyces spheroides NCIMB 11891. Steffensky M et al., J Biol Chem (2000) PMID:10801869 [3] Coumarin formation in novobiocin biosynthesis: beta-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 NovI. Chen H et al., Chem Biol (2001) PMID:11325587 [4] Genetic analysis of the biosynthesis of the pyrrole and carbamoyl moieties of coumermycin A1 and novobiocin. Xu H et al., Mol Genet Genomics (2002) PMID:12436260 [5] Initial characterization of novobiocic acid noviosyl transferase activity of NovM in biosynthesis of the antibiotic novobiocin. Freel Meyers CL et al., Biochemistry (2003) PMID:12680772 [6] Novobiocin biosynthesis: inactivation of the putative regulatory gene novE and heterologous expression of genes involved in aminocoumarin ring formation. Eustáquio AS et al., Arch Microbiol (2003) PMID:12736771 [7] Crystallization and preliminary X-ray studies on the putative dTDP sugar epimerase NovW from the novobiocin biosynthetic cluster of Streptomyces spheroides. Jakimowicz P et al., Acta Crystallogr D Biol Crystallogr (2003) PMID:12876368 [8] Discovery and antimicrobial properties of cathomycin, a new antibiotic produced by Streptomyces spheroides n. sp. HARRIS DA et al., Antibiot Annu (1955-1956) PMID:13355385 [9] The antimicrobial activity of cathomycin, a new antibiotic. CUCKLER AC et al., Antibiot Annu (1955-1956) PMID:13355386 [10] Characterization of NovP and NovN: completion of novobiocin biosynthesis by sequential tailoring of the noviosyl ring. Freel Meyers CL et al., Angew Chem Int Ed Engl (2004) PMID:14694473 [11] Functional characterizations of novWUS involved in novobiocin biosynthesis from Streptomyces spheroides. Thuy TT et al., Arch Biochem Biophys (2005) PMID:15752721 [12] Heterologous expression of novobiocin and clorobiocin biosynthetic gene clusters. Eustáquio AS et al., Appl Environ Microbiol (2005) PMID:15870333 [13] NovG, a DNA-binding protein acting as a positive regulator of novobiocin biosynthesis. Eustáquio AS et al., Microbiology (Reading) (2005) PMID:15942002 [14] NovJ/NovK catalyze benzylic oxidation of a beta-hydroxyl tyrosyl-S-pantetheinyl enzyme during aminocoumarin ring formation in novobiocin biosynthesis. Pacholec M et al., Biochemistry (2005) PMID:16171397 [15] CouO and NovO: C-methyltransferases for tailoring the aminocoumarin scaffold in coumermycin and novobiocin antibiotic biosynthesis. Pacholec M et al., Biochemistry (2005) PMID:16274243 [16] The 1.6-A resolution crystal structure of NovW: a 4-keto-6-deoxy sugar epimerase from the novobiocin biosynthetic gene cluster of Streptomyces spheroides. Jakimowicz P et al., Proteins (2006) PMID:16411240 [17] Characterisation of Streptomyces spheroides NovW and revision of its functional assignment to a dTDP-6-deoxy-D-xylo-4-hexulose 3-epimerase. Tello M et al., Chem Commun (Camb) (2006) PMID:16514445 [18] Molecular replacement in the 'twilight zone': structure determination of the non-haem iron oxygenase NovR from Streptomyces spheroides through repeated density modification of a poor molecular-replacement solution. Keller S et al., Acta Crystallogr D Biol Crystallogr (2006) PMID:17139092 [19] Crystallization and preliminary X-ray analysis of the O-methyltransferase NovP from the novobiocin-biosynthetic cluster of Streptomyces spheroides. Stevenson CE et al., Acta Crystallogr Sect F Struct Biol Cryst Commun (2007) PMID:17329822 [20] novE and novG act as positive regulators of novobiocin biosynthesis. Dangel V et al., Arch Microbiol (2008) PMID:18568336 [21] Crystallization and preliminary X-ray analysis of the O-carbamoyltransferase NovN from the novobiocin-biosynthetic cluster of Streptomyces spheroides. Gómez García I et al., Acta Crystallogr Sect F Struct Biol Cryst Commun (2008) PMID:18997325 [22] NovQ is a prenyltransferase capable of catalyzing the addition of a dimethylallyl group to both phenylpropanoids and flavonoids. Ozaki T et al., J Antibiot (Tokyo) (2009) PMID:19557032 [23] Transcriptional regulation of the novobiocin biosynthetic gene cluster. Dangel V et al., Microbiology (Reading) (2009) PMID:19762445 [24] The crystal structure of the novobiocin biosynthetic enzyme NovP: the first representative structure for the TylF O-methyltransferase superfamily. Gómez García I et al., J Mol Biol (2010) PMID:19857499 [25] Draft Genome Sequence of Streptomyces niveus NCIMB 11891, Producer of the Aminocoumarin Antibiotic Novobiocin. Flinspach K et al., Genome Announc (2014) PMID:24407644 [26] Streptonivicin, a new antibiotic. I. Discovery and biologic studies. SMITH CG et al., Antibiot Chemother (Northfield) (1956) PMID:24543916

Chemical products information

cathomycin Evidence:

Copy SMILES

C₃₁H₃₆N₂O₁₁

Chemical database entries
NPAtlas

List of genes involved in compound(s) production

Identifiers	Position	Product	Functions	Evidence	Extra
AAF67498.1 novE	4859 - 5512 (+)	regulatory protein NovE	Regulation	Knock-out Heterologous expression	copy AA seq copy Nt seq
AAF67499.1 novF	5588 - 6676 (+)	prephenate dehydrogenase	Precursor biosynthesis		copy AA seq copy Nt seq
AAF67500.1 novG	6782 - 7738 (+)	regulatory protein CloG	Regulation	Knock-out Heterologous expression	copy AA seq copy Nt seq
AAF67501.2 novH	7934 - 9736 (+)	peptide synthetase-like protein	Scaffold biosynthesis	Knock-out Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67502.1 novI	9740 - 10963 (+)	cytochrome P450	Scaffold biosynthesis	Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67503.1 novJ	10983 - 11771 (+)	b-ketotyrosyl-reductase	Scaffold biosynthesis	Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67504.1 novK	11768 - 12502 (+)	b-ketotyrosyl-reductase	Scaffold biosynthesis	Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67505.1 novL	12509 - 14092 (+)	amide synthetase	Scaffold biosynthesis	Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67506.1 novM	14106 - 15245 (+)	glycosyltransferase	Scaffold biosynthesis	Knock-out Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67507.2 novN	15274 - 17307 (+)	carbamoyltransferase	Scaffold biosynthesis	Knock-out Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67508.2 novO	17538 - 18230 (+)	methyltransferase	Tailoring	Knock-out Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67509.1 novP	18275 - 19063 (+)	O-methyltransferase	Tailoring	Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67510.2 novQ	19093 - 20064 (+)	ABBA prenyltransferase	Scaffold biosynthesis	Knock-out Heterologous expression Activity assay	copy AA seq copy Nt seq
AAF67511.1 novR	20061 - 20873 (+)	alpha-ketoacid-dependent oxygenase	Scaffold biosynthesis	Heterologous expression	copy AA seq copy Nt seq
AAF67512.1 novS	20870 - 21736 (+)	dTDP-4-keto-6-deoxyhexose reductase	Scaffold biosynthesis	Heterologous expression	copy AA seq copy Nt seq
AAF67513.1 novT	21770 - 22780 (+)	dTDP-glucose 4,6-dehydratase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAF67514.2 novU	22832 - 24094 (+)	C-methyltransferase	Scaffold biosynthesis	Heterologous expression	copy AA seq copy Nt seq
AAF67515.1 novV	24156 - 25049 (+)	dTDP-glucose synthase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAF67516.1 novW	25046 - 25669 (+)	dTDP-4-keto-6-deoxyglucose 3,5-epimerase	Scaffold biosynthesis	Heterologous expression	copy AA seq copy Nt seq
AFI47646.1 gyrB_R	26043 - 28076 (+)	resistant DNA gyrase subunit B	Resistance/immunity	Heterologous expression	copy AA seq copy Nt seq

Biosynthesis information

No biosynthesis information available for this record.

Annotation changelog

Entry version: 4

Date

Changes

Submitters

Reviewers

2022-10-07

Update chemical activity to schema version 2.11

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Entry version: 3

Date

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2022-09-15

Remove duplicated citations

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2022-09-15

Corrected gene identifiers

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2022-09-15

Updated bioactivity data

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Entry version: 2

Date

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2019-10-16

Migrated from v1.4

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2019-10-16

Updated compound(s) information (MIBiG Annotathon)

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2019-10-16

Updated compound(s) information (NPAtlas curation)

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Entry version: 1

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2015-06-12

Submitted

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Tailoring functions

Oxidoreductases: dehydrogenase oxygenase

novI: cytochrome P450

smcogs: SMCOG1007: cytochrome P450

novJ: short-chain dehydrogenase/reductase SDR

smcogs: SMCOG1001: short-chain dehydrogenase/reductase SDR

novK: short-chain dehydrogenase/reductase SDR

smcogs: SMCOG1001: short-chain dehydrogenase/reductase SDR

Transferases: glycosyltransferase methyltransferase transferase

novM: glycosyltransferase, MGT family

smcogs: SMCOG1062: glycosyltransferase, MGT family

novO: methyltransferase

smcogs: SMCOG1089: methyltransferase

novV: glucose-1-phosphate adenylyl/thymidylyltransferase

smcogs: SMCOG1064: glucose-1-phosphate adenylyl/thymidylyltransferase

Lyases: dehydratase

novS: NAD-dependent epimerase/dehydratase

smcogs: SMCOG1010: NAD-dependent epimerase/dehydratase

novT: NAD-dependent epimerase/dehydratase

smcogs: SMCOG1010: NAD-dependent epimerase/dehydratase

Ligases: ligase

novH: AMP-dependent synthetase and ligase

smcogs: SMCOG1002: AMP-dependent synthetase and ligase

novL: AMP-dependent synthetase and ligase

smcogs: SMCOG1002: AMP-dependent synthetase and ligase

Similar known clusters from MIBiG 4.0

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