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

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)

NAD:	NCTC11293_02478(pcpB_3) NCTC11293_04330(pcpB_5)

NHU:	H0264_27360(rox)

NYA:	LTV02_10235(rox)

NGP:	LTT66_29350(rox)

NSPU:

IFM12276_29920

NYU:	D7D52_23110(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

SFI:

SFUL_1083

SCB:	SCAB_86061 SCAB_87811

SHY:

SHJG_0647

SHO:	SHJGH_0480

SRC:	M271_08430

SBH:

SBI_09593

SVE:

SVEN_0481

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)

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)

SCAE:

IHE65_43335(rox)

SXT:	KPP03845_100623(otcC)

SLON:

LGI35_40485(rox)

SDRZ:

NEH16_30110 NEH16_30145

STUD:

STRTU_005099 STRTU_006113

SENG:

OJ254_23605(rox)

SGK:	PET44_15180(rox)

SJN:	RI060_16530(rox)

SFIY:

F0344_00610(rox)

SHAU:

K9S39_25475

SCOA:

QU709_36985 QU709_44865(rox)

SLAI:

P8A22_17835(rox)

SFP:	QUY26_06510(rox)

STRZ:

OYE22_18745

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)

AGLA:

OIE69_33595(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

ACAO:

NF551_06570

AKO:	N9A08_06510

AJR:	N2K98_06675(rox)

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

SGRG:

L0C25_18795(rox) L0C25_21785(rox)

KFL:

Kfla_1528

KQI:	F1D05_12920(rox) F1D05_27825(rox)

KSL:	OG809_31735(rox)

TFU:

Tfu_2841

THAO:

NI17_007430(rox)

TALX:

FOF52_15240(rox)

NDA:

Ndas_2748

NGV:	CDO52_19475

NCG:	KGD84_14630(rox)

SNAH:

OUQ99_22100(rox)

AMAZ:

LUW76_12925(rox) LUW76_38440(rox)

ACIR:

OG979_38770(rox)

SRO:

Sros_4669

NOA:	BKM31_47680

NOW:	GBF35_25415(rox)

NCX:	Nocox_22045(pcpB2) Nocox_33465(pcpB6)

NGN:	LCN96_27720 LCN96_32520(rox)

NFS:	OIE67_19335

MHAI:

OHB01_29390(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)

ARHD:

VSH64_45065(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

KUT:	JJ691_25120 JJ691_73520

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)

CROS:

N8J89_13815(rox) N8J89_17625(rox) N8J89_20295

UME:	RM788_51935(rox)

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

MCHL:

PVK74_24860(rox)

MPRN:

Q3V37_28625(rox)

MHAW:

RMN56_18980(rox) RMN56_19555(rox)

ASE:

ACPL_5566

AMS:	AMIS_39810

ACTN:

L083_3384

AFS:	AFR_14665 AFR_21600

ACTS:

ACWT_5436

AIH:	Aiant_03400

ACTR:

Asp14428_10770

ACTL:

L3i22_057780

ASIC:

Q0Z83_023790(rox) Q0Z83_032510

AOU:	ACTOB_005272(rox) ACTOB_005474

PLAB:

C6361_21750

PLAT:

C6W10_16710

PSUU:

Psuf_073720

ATL:	Athai_28500 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

» 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