KEGG ORTHOLOGY: K14731

ORTHOLOGY: K14731

Entry

K14731                      KO

Symbol

mlhB, chnC

Name

epsilon-lactone hydrolase [EC:3.1.1.83]

Pathway

map00903

Limonene degradation

map00930

Caprolactam degradation

map01120

Microbial metabolism in diverse environments

map01220

Degradation of aromatic compounds

Reaction

R03751

epsilon-caprolactone lactonohydrolase

R06390

monoterpene epsilon-lactone hydrolase

R06391

isopropenylmethyloxepan-2-one lactonohydrolase

R06392

4-isopropenyl-7-methyloxepan-2-one lactonohydrolase

R06393

monoterpene epsilon-lactone hydrolase

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00903 Limonene degradation
    K14731  mlhB, chnC; epsilon-lactone hydrolase
  09111 Xenobiotics biodegradation and metabolism
   00930 Caprolactam degradation
    K14731  mlhB, chnC; epsilon-lactone hydrolase
Enzymes [BR:ko01000]
3. Hydrolases
  3.1  Acting on ester bonds
   3.1.1  Carboxylic-ester hydrolases
    3.1.1.83  monoterpene epsilon-lactone hydrolase
     K14731  mlhB, chnC; epsilon-lactone hydrolase

Other DBs

COG:

COG0657

Genes

PPJ:	RK21_02866

PSYQ:

ACIC:

PPAI:

POL:

ATEM:

HCZ:	G9Q37_07250

DIS:	I3K84_12425

MLO:

mll1869

MLN:	A9174_17235

MOP:	Mesop_3308

MAM:	Mesau_03191

MHUA:

MCHK_3437

MJR:	EB229_17475

MERD:

EB233_14750

RLN:	J0663_02145

RBAN:

J2J98_14760

RHIB:

I8E17_06385

RJG:	CCGE525_02335

KAI:

K32_23640

PSCQ:

KHQ08_18415

BGEP:

ACP2YO_09515

LABT:

FIU93_30965(mlhB)

CAK:

Caul_5125

RUT:	FIU92_22375(mlhB)

PHAE:

N1037_21380

CON:	TQ29_18790 TQ29_18930

SUAM:

BOO69_22540

SULD:

B5M07_18400

SULP:

AADW22_15340

SPSE:

SULPSESMR1_04141(mlhB)

MALU:

KU6B_59960

LVS:	LOKVESSMR4R_03943(mlhB)

SBIN:

SPCL:

SPHD:

SBAR:

SPAG:

sphantq_03288(mlhB_1) sphantq_04480(mlhB_2)

PALJ:

LZC94_10710

NKO:	Niako_0270

MAUE:

ACFGVR_09955

MSA:	Mycsm_06641

MMC:

Mmcs_1513

MKM:

Mkms_1536

MFJ:	MFLOJ_25420

MSTO:

MSTO_28640

MSIM:

MSIM_15720

MSAK:

MSAS_01440

MKU:	I2456_11355

MPAA:

MKK62_01580

MHAF:

ACEL92_00680

MSM:	MSMEG_3010

MSG:	MSMEI_2935(lipR)

MSB:	LJ00_14980

MSN:	LI99_14985

MSH:	LI98_14990

MVQ:	MYVA_1608 MYVA_4988

MCHT:

MCHIJ_02190

MMON:

EWR22_07700

MGO:	AFA91_24835

MDF:	K0O62_05005

CCOE:

CETAM_13035(mlhB)

NFR:	ERS450000_00738(mlhB_1)

NNO:	NONO_c26760(bah)

RHA:	RHA1_ro06680

RPY:	Y013_12975

RRZ:	CS378_11575 CS378_11785

RKO:	JWS14_15895 JWS14_20950 JWS14_43755

RGO:	KYT97_23850

ROZ:	CBI38_25685

RPSK:

JWS13_28455 JWS13_31000 JWS13_42110 JWS13_42175 JWS13_43350

RHOO:

RHOJ:

RHOS:

RHOQ:

RHJS:

OYT95_22945 OYT95_35445

RHZQ:

GO592_34175

RHPD:

U9J23_25905

RHWB:

FND50_32810 FND50_33400

RHWY:

GFS60_04234 GFS60_06853 GFS60_06878

RHMM:

ISO16_23390

RHZP:

HYG77_20490 HYG77_24140 HYG77_34920 HYG77_34975

RHRD:

RDE2_46090

GOR:

KTR9_3184

GTA:	BCM27_16265

GOD:	GKZ92_20420 GKZ92_20525

SGRF:

SGFS_010390

SCB:	SCAB_77011

SBH:

SBI_01199

SLS:	SLINC_0027

SDX:	C4B68_05970

SAQU:

EJC51_02305

SDEC:

L3078_00625 L3078_03500

SAKB:

K1J60_39635 K1J60_42320

SCAE:

IHE65_45115

SJN:	RI060_17530

SCOA:

QU709_03220 QU709_42465

KBU:	Q4V64_50825

STRL:

STRK:

ABRY:

MHOS:

MSF:	IT882_15885

MPRL:

AB0870_17555

PSAI:

C3B54_111350

HEA:	HL652_02370

GMN:	GMOLON4_1493(chnC)

ARTP:

E5206_14690

GMY:

XH9_01110

SPUE:

AB5L97_16920

JAY:	H7A72_06395

BSPO:

L1F31_01650 L1F31_01865 L1F31_11510

MICG:

GJV80_04835

KSL:	OG809_40790

AGRA:

AMAZ:

ACTQ:

SACG:

AMQ:	AMETH_2426 AMETH_3877

AAB:	A4R43_22535

AMYY:

YIM_32910(mlhB3)

ATHM:

AMYD:

PDX:

PSEQ:

PECQ:

PAUT:

PBRO:

PPEL:

H6H00_18840 H6H00_19435 H6H00_19590

PALQ:

PaSha_23240

PMAD:

BAY61_09880 BAY61_19415

ACTY:

OG774_12490 OG774_29150

AIH:	Aiant_00540

ACTE:

ACTI_51590

AFS:

AFR_22850

DVC:	Dvina_29365

DMAT:

Dmats_24580

DAUR:

Daura_17400

SNA:

Snas_2426

EKE:	EK0264_02330

BSOL:

FSW04_20600

SBAE:

DSM104329_02046(mlhB_1)

AG:	BAC80218(chnC) CAC17806(mlhB)

» show all

Reference

PMID:11157238

Authors

van der Vlugt-Bergmans CJ, van der Werf MJ

Title

Genetic and biochemical characterization of a novel monoterpene epsilon-lactone hydrolase from Rhodococcus erythropolis DCL14.

Journal

Appl Environ Microbiol 67:733-41 (2001)
DOI:10.1128/AEM.67.2.733-741.2001

Sequence

[ag:CAC17806]

Reference

PMID:10543838

Authors

Iwaki H, Hasegawa Y, Teraoka M, Tokuyama T, Bergeron H, Lau PC

Title

Identification of a transcriptional activator (ChnR) and a 6-oxohexanoate dehydrogenase (ChnE) in the cyclohexanol catabolic pathway in Acinetobacter sp. Strain NCIMB 9871 and localization of the genes that encode them.

Journal

Appl Environ Microbiol 65:5158-62 (1999)
DOI:10.1128/AEM.65.11.5158-5162.1999

Sequence

[ag:BAC80218]

LinkDB

ENZYME: 3.1.1.83

Entry

EC 3.1.1.83                 Enzyme

Name

monoterpene epsilon-lactone hydrolase;
MLH

Class

Hydrolases;
Acting on ester bonds;
Carboxylic-ester hydrolases

Sysname

isoprop(en)ylmethyloxepan-2-one lactonohydrolase

Reaction(IUBMB)

(1) isoprop(en)ylmethyloxepan-2-one + H2O = 6-hydroxyisoprop(en)ylmethylhexanoate (general reaction);
(2) 4-isopropenyl-7-methyloxepan-2-one + H2O = 6-hydroxy-3-isopropenylheptanoate [RN:R06390 R06392];
(3) 7-isopropyl-4-methyloxepan-2-one + H2O = 6-hydroxy-3,7-dimethyloctanoate [RN:R08979]

Reaction(KEGG)

R06390 R06392 R08979;
(other) R03751 R06391 R06393

Substrate

isoprop(en)ylmethyloxepan-2-one;
H2O [CPD:C00001];
4-isopropenyl-7-methyloxepan-2-one [CPD:C11414];
7-isopropyl-4-methyloxepan-2-one [CPD:C18066]

Product

6-hydroxyisoprop(en)ylmethylhexanoate;
6-hydroxy-3-isopropenylheptanoate [CPD:C11417];
6-hydroxy-3,7-dimethyloctanoate [CPD:C18067]

Comment

The enzyme catalyses the ring opening of epsilon-lactones which are formed during degradation of dihydrocarveol by the Gram-positive bacterium Rhodococcus erythropolis DCL14. The enzyme also acts on ethyl caproate, indicating that it is an esterase with a preference for lactones (internal cyclic esters). The enzyme is not stereoselective.

History

EC 3.1.1.83 created 2008

Pathway

ec00903

Limonene degradation

ec00930

Caprolactam degradation

ec01120

Microbial metabolism in diverse environments

Orthology

K14731

epsilon-lactone hydrolase

Genes

PPJ:	RK21_02866

PSYQ:

HXW90_20585

ACIC:

IOD65_14190

PPAI:

E1956_37465

POL:

Bpro_5566

ATEM:

PQV96_11840

HCZ:	G9Q37_07250

DIS:	I3K84_12425

MLO:

mll1869

MLN:	A9174_17235

MOP:	Mesop_3308

MAM:	Mesau_03191

MHUA:

MCHK_3437

MJR:	EB229_17475

MERD:

EB233_14750

RLN:	J0663_02145

RBAN:

J2J98_14760

RHIB:

I8E17_06385

RJG:	CCGE525_02335

KAI:

K32_23640

PSCQ:

KHQ08_18415

BGEP:

ACP2YO_09515

LABT:

FIU93_30965(mlhB)

CAK:

Caul_5125

RUT:	FIU92_22375(mlhB)

PHAE:

N1037_21380

CON:	TQ29_18790 TQ29_18930

SUAM:

BOO69_22540

SULD:

B5M07_18400

SULP:

AADW22_15340

SPSE:

SULPSESMR1_04141(mlhB)

MALU:

KU6B_59960

LVS:	LOKVESSMR4R_03943(mlhB)

SBIN:

SBA_ch1_21760

SPCL:

F9288_06105

SPHD:

HY78_29685

SBAR:

H5V43_03345

SPAG:

sphantq_03288(mlhB_1) sphantq_04480(mlhB_2)

PALJ:

LZC94_10710

NKO:	Niako_0270

MAUE:

ACFGVR_09955

MSA:	Mycsm_06641

MMC:

Mmcs_1513

MKM:

Mkms_1536

MFJ:	MFLOJ_25420

MSTO:

MSTO_28640

MSIM:

MSIM_15720

MSAK:

MSAS_01440

MKU:	I2456_11355

MPAA:

MKK62_01580

MHAF:

ACEL92_00680

MSM:	MSMEG_3010

MSG:	MSMEI_2935(lipR)

MSB:	LJ00_14980

MSN:	LI99_14985

MSH:	LI98_14990

MVQ:	MYVA_1608 MYVA_4988

MCHT:

MCHIJ_02190

MMON:

EWR22_07700

MGO:	AFA91_24835

MDF:	K0O62_05005

CCOE:

CETAM_13035(mlhB)

NFR:	ERS450000_00738(mlhB_1)

NNO:	NONO_c26760(bah)

RHA:	RHA1_ro06680

RPY:	Y013_12975

RRZ:	CS378_11575 CS378_11785

RKO:	JWS14_15895 JWS14_20950 JWS14_43755

RGO:	KYT97_23850

ROZ:	CBI38_25685

RPSK:

JWS13_28455 JWS13_31000 JWS13_42110 JWS13_42175 JWS13_43350

RHOO:

RA302_30930

RHOJ:

JVH1_02765

RHOS:

QWW67_23460

RHOQ:

QWW98_23470

RHJS:

OYT95_22945 OYT95_35445

RHZQ:

GO592_34175

RHPD:

U9J23_25905

RHWB:

FND50_32810 FND50_33400

RHWY:

GFS60_04234 GFS60_06853 GFS60_06878

RHMM:

ISO16_23390

RHZP:

HYG77_20490 HYG77_24140 HYG77_34920 HYG77_34975

RHRD:

RDE2_46090

GOR:

KTR9_3184

GTA:	BCM27_16265

GOD:	GKZ92_20420 GKZ92_20525

SGRF:

SGFS_010390

SCB:	SCAB_77011

SBH:

SBI_01199

SLS:	SLINC_0027

SDX:	C4B68_05970

SAQU:

EJC51_02305

SDEC:

L3078_00625 L3078_03500

SAKB:

K1J60_39635 K1J60_42320

SCAE:

IHE65_45115

SJN:	RI060_17530

SCOA:

QU709_03220 QU709_42465

KBU:	Q4V64_50825

STRL:

HEP84_49955

STRK:

R2B38_45745

ABRY:

NYE86_02710

MHOS:

CXR34_00665

MSF:	IT882_15885

MPRL:

AB0870_17555

PSAI:

C3B54_111350

HEA:	HL652_02370

GMN:	GMOLON4_1493(chnC)

ARTP:

E5206_14690

GMY:

XH9_01110

SPUE:

AB5L97_16920

JAY:	H7A72_06395

BSPO:

L1F31_01650 L1F31_01865 L1F31_11510

MICG:

GJV80_04835

KSL:	OG809_40790

AGRA:

AGRA3207_001538

AMAZ:

LUW76_44795

ACTQ:

OG417_03105

SACG:

FDZ84_29665

AMQ:	AMETH_2426 AMETH_3877

AAB:	A4R43_22535

AMYY:

YIM_32910(mlhB3)

ATHM:

L1857_19155

AMYD:

K1T34_46470

PDX:

Psed_0489

PSEQ:

AD006_28260

PECQ:

AD017_28655

PAUT:

Pdca_39560

PBRO:

HOP40_29310

PPEL:

H6H00_18840 H6H00_19435 H6H00_19590

PALQ:

PaSha_23240

PMAD:

BAY61_09880 BAY61_19415

ACTY:

OG774_12490 OG774_29150

AIH:	Aiant_00540

ACTE:

ACTI_51590

AFS:

AFR_22850

DVC:	Dvina_29365

DMAT:

Dmats_24580

DAUR:

Daura_17400

SNA:

Snas_2426

EKE:	EK0264_02330

BSOL:

FSW04_20600

SBAE:

DSM104329_02046(mlhB_1)

» show all

Reference

1 [PMID:11157238]

Authors

van der Vlugt-Bergmans CJ, van der Werf MJ

Title

Genetic and biochemical characterization of a novel monoterpene epsilon-lactone hydrolase from Rhodococcus erythropolis DCL14.

Journal

Appl Environ Microbiol 67:733-41 (2001)
DOI:10.1128/AEM.67.2.733-741.2001

Sequence

[ag:CAC17806]

Other DBs

ExplorEnz - The Enzyme Database:

3.1.1.83

IUBMB Enzyme Nomenclature:

3.1.1.83

ExPASy - ENZYME nomenclature database:

3.1.1.83

BRENDA, the Enzyme Database:

3.1.1.83

LinkDB

REACTION: R06390

Entry

R06390                      Reaction

Name

monoterpene epsilon-lactone hydrolase

Definition

(4R,7R)-4-Isopropenyl-7-methyl-2-oxo-oxepanone + H2O <=> (3R)-6-Hydroxy-3-isopropenyl-heptanoate

Equation

C11402 + C00001 <=> C11404

Reaction class

RC01505

C11402_C11404

Enzyme

3.1.1.83

Pathway

rn00903

Limonene degradation

rn01120

Microbial metabolism in diverse environments

rn01220

Degradation of aromatic compounds

Brite

Enzymatic reactions [BR:br08201]
3. Hydrolase reactions
  3.1  Acting on ester bonds
   3.1.1  Carboxylic-ester hydrolases
    3.1.1.83
     R06390  (4R,7R)-4-Isopropenyl-7-methyl-2-oxo-oxepanone + H2O <=> (3R)-6-Hydroxy-3-isopropenyl-heptanoate

Orthology

K14731

epsilon-lactone hydrolase [EC:3.1.1.83]

Other DBs

RHEA:

32514

LinkDB

DBGET integrated database retrieval system