KEGG ENZYME: 1.14.13.211

ENZYME: 1.14.13.211

Entry

EC 1.14.13.211              Enzyme

Name

rifampicin monooxygenase;
RIF-O;
ROX;
RIFMO;
rifampicin:NAD(P)H:oxygen oxidoreductase (2'-N-hydroxyrifampicin-forming) (incorrect)

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor

Sysname

rifampicin:NAD(P)H:oxygen oxidoreductase (2-hydroxy-2,27-secorifampicin-forming; ring-cleaving)

Reaction(IUBMB)

rifampicin + NAD(P)H + O2 = 2-hydroxy-2,27-secorifampicin + NAD(P)+ + H2O [RN:R11151 R11152]

Reaction(KEGG)

R11151 R11152

Substrate

rifampicin [CPD:C06688];
NADH [CPD:C00004];
NADPH [CPD:C00005];
O2 [CPD:C00007]

Product

2-hydroxy-2,27-secorifampicin [CPD:C22649];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006];
H2O [CPD:C00001]

Comment

The enzyme has been found in a variety of environmental bacteria, notably Rhodococcus, Nocardia, and Streptomyces. It hydroxylates C-2 of rifampicin leading to its macro-ring cleaving.

History

EC 1.14.13.211 created 2016, modified 2022

Orthology

K21267

rifampicin monooxygenase

Genes

LMB:	C9I47_1848

RHJ:	HZY79_00590

MFB:	MFUL124B02_23965

MMC:

Mmcs_2661

MKM:

Mkms_2706

MJL:

Mjls_2691

MYV:	G155_10900

MSM:	MSMEG_2252

MSG:	MSMEI_2197

MSB:	LJ00_11210

MSN:	LI99_11210

MSH:	LI98_11215

MCB:	Mycch_0828

MFT:	XA26_22420

MTHN:

4412656_04597(pcpB_2)

MCHT:

MCHIJ_38720

MMON:

EWR22_14160(rox)

ASD:

AS9A_2324

NFA:	NFA_35380(rox)

NFR:	ERS450000_00511(pcpB_1)

NBR:	O3I_020820

NNO:	NONO_c65020

NSL:	BOX37_12060

NSR:	NS506_05823

NTP:	CRH09_14830

NOZ:	DMB37_35700 DMB37_35980(rox)

NOD:	FOH10_14330(rox)

NAH:	F5544_22005(rox) F5544_22150(rox) F5544_28800

NAD:	NCTC11293_02478(pcpB_3) NCTC11293_04330(pcpB_5)

NHU:	H0264_27360(rox)

NYA:	LTV02_10235(rox)

NGP:	LTT66_29350(rox)

RHA:	RHA1_ro07160

RER:

RER_20250

REY:

O5Y_09730

REB:	XU06_09965

RQI:	C1M55_10225(iri)

ROP:

ROP_37320

ROA:	Pd630_LPD03904

RAV:	AAT18_01260

RRZ:	CS378_17530

RCR:	NCTC10994_00474(pcpB)

RTM:	G4H71_05850(rox)

RKO:	JWS14_00845(rox) JWS14_21170(rox)

RGO:	KYT97_23045(iri)

ROZ:	CBI38_15390

RPSK:

JWS13_23710(rox) JWS13_45025(rox)

REQ:

REQ_41440

GOM:	D7316_01072(otcC)

SCO:	SCO7626(SC2H2.24c)

SALB:

XNR_3358

SCB:	SCAB_86061 SCAB_87811

SHY:

SHJG_0647

SHO:	SHJGH_0480

SRC:	M271_08430

SBH:

SBI_09593

SVE:

SVEN_0481

SFI:

SFUL_1083

SLV:	SLIV_01185

SGU:	SGLAU_30650

SVT:	SVTN_01150 SVTN_31975

SLD:

T261_4795

SLC:	SL103_19710

STRM:

M444_16460

STRC:

AA958_04415

SPRI:

SPRI_0130 SPRI_7223

SCZ:	ABE83_30235

SCX:	AS200_01595 AS200_42295 AS200_44240

SRW:	TUE45_01151(pcpB_1)

SPAV:

Spa2297_00880

SCLF:

BB341_28050

SKY:	D0C37_14590(rox)

SALW:

CP975_16240(rox)

SGM:	GCM10017557_73960 GCM10017557_80250 GCM10017557_82510

SCAD:

DN051_36265(rox)

SPHW:

NFX46_24900

STRD:

NI25_36215

SGV:	B1H19_19290

SALF:

SMD44_07122

SALJ:

SMD11_6238 SMD11_6656

SLX:	SLAV_11085(pcpB4)

STRO:

STRMOE7_35915

SFK:

KY5_0184

SGE:	DWG14_01874(otcC_2) DWG14_06120(otcC_4)

SRJ:

SRO_6922

SLK:	SLUN_18280

SGD:	ELQ87_04590(rox)

SCYA:

EJ357_38800(rox)

SAST:

CD934_16465

SNQ:	CP978_28085(rox)

STIR:

DDW44_23910(rox)

SKA:	CP970_36715 CP970_42000(rox)

SGZ:	C0216_15010

SVN:	CP980_05055(rox)

SRK:	FGW37_01015(rox)

SFIC:

EIZ62_19545(rox)

SSPO:

DDQ41_28065(rox)

SPAD:

DVK44_19705

SFY:	GFH48_27575(rox)

SGF:	HEP81_07258

SCAV:

CVT27_04410

SSEO:

D0Z67_04825(rox)

SBY:	H7H31_19150

SRIM:

CP984_11965(rox)

SSUB:

CP968_26650(rox)

SPHV:

F9278_01720(rox)

SCIN:

CP977_05620

STSU:

B7R87_08145

SCHA:

CP983_06175(rox)

SGX:	H4W23_38295(rox)

SBAT:

G4Z16_11275(rox)

SNF:	JYK04_00573(otcC_3) JYK04_00810(otcC_4)

SPLA:

CP981_36700(rox)

SATA:

C5746_22555

SHUN:

DWB77_00315(otcC_1) DWB77_07437(otcC_8)

SFEU:

IM697_28010(rox) IM697_28330(rox)

SLIA:

HA039_18840(rox)

SDW:	K7C20_21610(rox)

SVD:	CP969_12535(rox)

SAUH:

SU9_002615(rox)

SMOB:

J7W19_03885(rox)

SPRA:

CP972_16765(rox)

SPEU:

CGZ69_33670

SINE:

KI385_00320(rox)

SLF:	JEQ17_20780(rox) JEQ17_46830(rox)

SDEC:

L3078_02060(rox)

SAOV:

G3H79_04805(rox)

SDUR:

M4V62_36675(rox)

SRUG:

F0345_15785(rox)

SAKB:

K1J60_43335(rox)

STAA:

LDH80_07250(rox)

SNIG:

HEK616_75140

SVIO:

HWN34_17160(rox)

KSK:

KSE_07580

KAB:	B7C62_04415

KIT:	CFP65_0086

KIS:	HUT16_02905

STRI:

C7M71_013320(rox)

YIA:	LO772_01570(rox) LO772_34465

STRH:

GXP74_26755(rox)

LSE:	F1C12_20910

MWA:	E4K62_09675

MCAW:

F6J84_06195

MLZ:	F6J85_09290

MVD:	AWU67_08055

SALD:

FVA74_05230

PLAP:

EAO79_07025

HEA:	HL652_14235

ART:

Arth_1940

ARE:	AL755_21720

ARW:	MB46_12895

ARQ:	BWQ92_15450

AJG:	KKR91_06395

KFV:	AS188_07380

BKI:	M4486_02155

BHH:	Bra3105_00415

CDON:

KKR89_04035

CWAN:

KG103_04260

CFEN:

KG102_02750(rox)

NDK:	I601_2824(pcpB)

NMES:

H9L09_10960(rox)

NPC:	KUV85_07115

KFL:

Kfla_1528

KQI:	F1D05_12920(rox) F1D05_27825(rox) F1D05_30245

TFU:

Tfu_2841

THAO:

NI17_007430(rox)

TALX:

FOF52_15240(rox)

NDA:

Ndas_2748

NGV:	CDO52_19475

SNAH:

OUQ99_22100(rox)

SRO:

Sros_4669

NOA:	BKM31_47680

NOW:	GBF35_25415(rox)

NCX:	Nocox_22045(pcpB2) Nocox_33465(pcpB6)

NGN:	LCN96_27720 LCN96_32520(rox)

FRE:	Franean1_4133

FRI:	FraEuI1c_3695

SEN:

SACE_4643

SACG:

FDZ84_31035(rox)

SACC:

EYD13_11195(pcpB2)

AMD:

AMED_1629

AMN:

RAM_08270

AMM:

AMES_1617

AMZ:

B737_1618

AOI:	AORI_3930(mhpA)

AJA:	AJAP_19340

AMYC:

CU254_15995 CU254_19080

AMYB:

BKN51_12065 BKN51_12125

AAB:	A4R43_00220 A4R43_03555

AMYY:

YIM_09330(pcpB1) YIM_16465(pcpB3)

AORI:

SD37_20160

APRT:

MUY14_42755(rox)

AROO:

NQK81_02955(rox)

ATHM:

L1857_07040(rox)

PDX:

Psed_0253

PSEE:

FRP1_14780

PSEQ:

AD006_22445

PECQ:

AD017_02030

PAUT:

Pdca_02570

PPEL:

H6H00_02695(rox)

APRE:

CNX65_10055

AMI:

Amir_2013

SESP:

BN6_42360 BN6_44160

SSYI:

EKG83_16990(rox)

KAL:

KALB_4274

KPHY:

AOZ06_27820

LED:	BBK82_36645 BBK82_39920

ACTI:

UA75_15955

ACAD:

UA74_15395

ALO:

CRK57149

PMAD:

BAY61_24140

SACE:

GIY23_21205(rox)

ACTU:

Actkin_03072(pcpB_3) Actkin_04232(pcpB_4)

STP:	Strop_1498

MAU:	Micau_0723

MIL:

ML5_0967

MICB:

MicB006_0754

MTUA:

CSH63_20890

MICH:

FJK98_20740 FJK98_25315(rox)

MTEM:

GCE86_10990(rox)

MCAB:

HXZ27_08900(rox)

MSAG:

GCM10017556_36290

VMA:	VAB18032_19300

VER:	HUT12_17995(rox)

MENO:

Jiend_13080

ASE:

ACPL_5566

AMS:	AMIS_39810

ACTN:

L083_3384

AFS:	AFR_14665 AFR_21600

ACTS:

ACWT_5436

AIH:	Aiant_03400

ACTR:

Asp14428_10770

PLAB:

C6361_21750

PLAT:

C6W10_16710

PSUU:

Psuf_073720

ATL:	Athai_28500 Athai_49560 Athai_60150

ASER:

Asera_46090

PRY:	Prubr_19000

CATI:

CS0771_48580

DVC:	Dvina_10845 Dvina_22025(rox)

DFU:	Dfulv_36030(rox)

DROS:

Drose_13170(rox)

DAUR:

Daura_18630(rox) Daura_28680 Daura_31715(rox)

DMAT:

Dmats_10440 Dmats_17640(rox)

SNA:

Snas_3217

CWO:

Cwoe_4431

PFER:

IRI77_18695

» show all

Reference

1 [PMID:8980786]

Authors

Andersen SJ, Quan S, Gowan B, Dabbs ER

Title

Monooxygenase-like sequence of a Rhodococcus equi gene conferring increased resistance to rifampin by inactivating this antibiotic.

Journal

Antimicrob Agents Chemother 41:218-21 (1997)
DOI:10.1128/AAC.41.1.218

Sequence

[ag:AAB41059]

Reference

2 [PMID:19942945]

Authors

Hoshino Y, Fujii S, Shinonaga H, Arai K, Saito F, Fukai T, Satoh H, Miyazaki Y, Ishikawa J

Title

Monooxygenation of rifampicin catalyzed by the rox gene product of Nocardia farcinica: structure elucidation, gene identification and role in drug resistance.

Journal

J Antibiot (Tokyo) 63:23-8 (2010)
DOI:10.1038/ja.2009.116

Sequence

[nfa:NFA_35380]

Reference

3 [PMID:29398560]

Authors

Koteva K, Cox G, Kelso JK, Surette MD, Zubyk HL, Ejim L, Stogios P, Savchenko A, Sorensen D, Wright GD

Title

Rox, a Rifamycin Resistance Enzyme with an Unprecedented Mechanism of Action.

Journal

Cell Chem Biol 25:403-412.e5 (2018)
DOI:10.1016/j.chembiol.2018.01.009

Sequence

[sve:SVEN_0481]

Reference

4 [PMID:29578336]

Authors

Liu LK, Dai Y, Abdelwahab H, Sobrado P, Tanner JJ.

Title

Structural Evidence for Rifampicin Monooxygenase Inactivating Rifampicin by Cleaving Its Ansa-Bridge.

Journal

Biochemistry 57:2065-2068 (2018)
DOI:10.1021/acs.biochem.8b00190

Sequence

[nfa:NFA_35380]

Other DBs

ExplorEnz - The Enzyme Database:

1.14.13.211

IUBMB Enzyme Nomenclature:

1.14.13.211

ExPASy - ENZYME nomenclature database:

1.14.13.211

BRENDA, the Enzyme Database:

1.14.13.211

All links

Chemical substance (9)   
   KEGG COMPOUND (9)   
Chemical reaction (3)   
   KEGG REACTION (2)   
   KEGG RCLASS (1)   
Gene (293)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (288)   
   KEGG MGENES (4)   
Protein sequence (6)   
   UniProt (3)   
   SWISS-PROT (3)   
Protein domain (2)   
   InterPro (2)   
All databases (313)   

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