KEGG ORTHOLOGY: K20421

ORTHOLOGY: K20421

Entry

K20421                      KO

Symbol

ncsB1

Name

2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase [EC:2.1.1.303]

Pathway

map01059

Biosynthesis of enediyne antibiotics

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00830

Neocarzinostatin naphthoate moiety biosynthesis, malonyl-CoA => 2-hydroxy-5-methyl-1-naphthoate => 2-hydroxy-7-methoxy-5-methyl-1-naphthoyl-CoA

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   01059 Biosynthesis of enediyne antibiotics
    K20421  ncsB1; 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase
09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    K20421  ncsB1; 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase
Enzymes [BR:ko01000]
2. Transferases
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.303  2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase
     K20421  ncsB1; 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase
Polyketide biosynthesis proteins [BR:ko01008]
Polyketide tailoring proteins
  Methylase
   K20421  ncsB1; 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase

Other DBs

RN:

R10963

Genes

CLIA:

C3E79_07185

NCY:	NOCYR_3137(dnrK)

NNO:	NONO_c58190

NTP:	CRH09_14165 CRH09_23690 CRH09_25100 CRH09_33960

NOD:	FOH10_15005 FOH10_16430

NAH:	F5544_21445

NIE:	KV110_22915

NHU:	H0264_26770

RHU:	A3Q40_00430(rdmB)

DTM:	BJL86_2741

SMA:	SAVERM_2382

SSX:	SACTE_5196 SACTE_6329

SHY:	SHJG_8512 SHJG_8515

SHO:	SHJGH_8272 SHJGH_8275

SSOI:

I1A49_00935

SCW:	TU94_01395

SXI:	SXIM_36010

SPRI:

SPRI_3765

SLE:	sle_66100(sle_66100)

SPHW:

NFX46_33070

SLS:	SLINC_1337 SLINC_5831

SALU:

DC74_6556

SALL:

SAZ_34135

SAUO:

BV401_01185

SGV:	B1H19_02505

STIR:

DDW44_27895

SKA:	CP970_39755

SGZ:	C0216_12105

SGAL:

SRIM:

SCIN:

STSU:

SCOE:

STUI:

SCHF:

SFEU:

SROI:

SDD:	D9753_27325

STAA:

LDH80_10680

MIH:	BJP65_10025

SKE:	Sked_14480

CELZ:

E5225_16810

NRO:	K8W59_02610

KFL:

Kfla_6058

KQI:	F1D05_14965

NAL:	B005_2465(dnrK)

NEX:	NE857_03915

NOA:	BKM31_13620 BKM31_42290

SEN:

SACE_4650

SACG:

FDZ84_19175 FDZ84_28800 FDZ84_37280

AMD:

AMN:

AMM:

AMZ:

AOI:

AJA:	AJAP_06605

AMYC:

CU254_34420

AMYB:

BKN51_25805

AAB:	A4R43_20175

AMYY:

YIM_09465(dnrK1) YIM_15125(dnrK2)

AORI:

SD37_05090 SD37_08075

APRT:

MUY14_19315

AROO:

NQK81_33475

PDX:

Psed_0831

PSEE:

FRP1_29540 FRP1_30105

PECQ:

AD017_32745 AD017_33050

PHH:	AFB00_04185 AFB00_16770

PBRO:

APRE:

AMI:

SESP:

SSYI:

EKG83_21075 EKG83_31050

KPHY:

AOZ06_09075

LED:	BBK82_29280

AHM:	TL08_06695

ACTI:

UA75_06455

ACAD:

UA74_06455

AHG:	AHOG_06225(dnrK1)

PMAD:

BAY61_07660 BAY61_19805

SACE:

GIY23_05190

STP:	Strop_2214

SAQ:

Sare_4955

MAU:	Micau_3716

MIL:

ML5_4683

MICB:

MicB006_2815

MICH:

FJK98_09300

AMS:	AMIS_34740

PRY:	Prubr_63830

DVC:	Dvina_22655

NHY:	JQS43_20915

CCAZ:

COUCH_30655

KBS:	EPA93_15280

SUS:

Acid_5654

PFER:

IRI77_02260

AG:	AAM77984(ncsB1)

» show all

Reference

PMID:18387946

Authors

Luo Y, Lin S, Zhang J, Cooke HA, Bruner SD, Shen B

Title

Regiospecific O-methylation of naphthoic acids catalyzed by NcsB1, an O-methyltransferase involved in the biosynthesis of the enediyne antitumor antibiotic neocarzinostatin.

Journal

J Biol Chem 283:14694-702 (2008)
DOI:10.1074/jbc.M802206200

Sequence

[ag:AAM77984]

LinkDB

ENZYME: 2.1.1.303

Entry

EC 2.1.1.303                Enzyme

Name

2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase;
NcsB1;
neocarzinostatin O-methyltransferase

Class

Transferases;
Transferring one-carbon groups;
Methyltransferases

Sysname

S-adenosyl-L-methionine:2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase

Reaction(IUBMB)

S-adenosyl-L-methionine + 2,7-dihydroxy-5-methyl-1-naphthoate = S-adenosyl-L-homocysteine + 2-hydroxy-7-methoxy-5-methyl-1-naphthoate [RN:R10963]

Reaction(KEGG)

R10963

Substrate

S-adenosyl-L-methionine [CPD:C00019];
2,7-dihydroxy-5-methyl-1-naphthoate [CPD:C20857]

Product

S-adenosyl-L-homocysteine [CPD:C00021];
2-hydroxy-7-methoxy-5-methyl-1-naphthoate [CPD:C20841]

Comment

The enzyme from the bacterium Streptomyces carzinostaticus is involved in the biosynthesis of 2-hydroxy-7-methoxy-5-methyl-1-naphthoate. This compound is part of the enediyne chromophore of the antitumor antibiotic neocarzinostatin. In vivo the enzyme catalyses the regiospecific methylation at the 7-hydroxy group of its native substrate 2,7-dihydroxy-5-methyl-1-naphthoate. In vitro it also recognizes other dihydroxynaphthoic acids and catalyses their regiospecific O-methylation.

History

EC 2.1.1.303 created 2014

Pathway

ec01059

Biosynthesis of enediyne antibiotics

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K20421

2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase

Genes

CLIA:

C3E79_07185

NCY:	NOCYR_3137(dnrK)

NNO:	NONO_c58190

NTP:	CRH09_14165 CRH09_23690 CRH09_25100 CRH09_33960

NOD:	FOH10_15005 FOH10_16430

NAH:	F5544_21445

NIE:	KV110_22915

NHU:	H0264_26770

RHU:	A3Q40_00430(rdmB)

DTM:	BJL86_2741

SMA:	SAVERM_2382

SSX:	SACTE_5196 SACTE_6329

SHY:	SHJG_8512 SHJG_8515

SHO:	SHJGH_8272 SHJGH_8275

SSOI:

I1A49_00935

SCW:	TU94_01395

SXI:	SXIM_36010

SPRI:

SPRI_3765

SLE:	sle_66100(sle_66100)

SPHW:

NFX46_33070

SLS:	SLINC_1337 SLINC_5831

SALU:

DC74_6556

SALL:

SAZ_34135

SAUO:

BV401_01185

SGV:	B1H19_02505

STIR:

DDW44_27895

SKA:	CP970_39755

SGZ:	C0216_12105

SGAL:

CP966_11160

SRIM:

CP984_35640

SCIN:

CP977_27955

STSU:

B7R87_22010

SCOE:

CP976_32885

STUI:

GCM10017668_37980

SCHF:

IPT68_15470

SFEU:

IM697_24295

SROI:

IAG44_38680

SDD:	D9753_27325

STAA:

LDH80_10680

MIH:	BJP65_10025

SKE:	Sked_14480

CELZ:

E5225_16810

NRO:	K8W59_02610

KFL:

Kfla_6058

KQI:	F1D05_14965

NAL:	B005_2465(dnrK)

NEX:	NE857_03915

NOA:	BKM31_13620 BKM31_42290

SEN:

SACE_4650

SACG:

FDZ84_19175 FDZ84_28800 FDZ84_37280

AMD:

AMED_3230

AMN:

RAM_16420

AMM:

AMES_3195

AMZ:

B737_3195

AOI:

AORI_6472

AJA:	AJAP_06605

AMYC:

CU254_34420

AMYB:

BKN51_25805

AAB:	A4R43_20175

AMYY:

YIM_09465(dnrK1) YIM_15125(dnrK2)

AORI:

SD37_05090 SD37_08075

APRT:

MUY14_19315

AROO:

NQK81_33475

PDX:

Psed_0831

PSEE:

FRP1_29540 FRP1_30105

PECQ:

AD017_32745 AD017_33050

PHH:	AFB00_04185 AFB00_16770

PBRO:

HOP40_34045

APRE:

CNX65_21955

AMI:

Amir_4382

SESP:

BN6_04400

SSYI:

EKG83_21075 EKG83_31050

KPHY:

AOZ06_09075

LED:	BBK82_29280

AHM:	TL08_06695

ACTI:

UA75_06455

ACAD:

UA74_06455

AHG:	AHOG_06225(dnrK1)

PMAD:

BAY61_07660 BAY61_19805

SACE:

GIY23_05190

STP:	Strop_2214

SAQ:

Sare_4955

MAU:	Micau_3716

MIL:

ML5_4683

MICB:

MicB006_2815

MICH:

FJK98_09300

AMS:	AMIS_34740

PRY:	Prubr_63830

DVC:	Dvina_22655

NHY:	JQS43_20915

CCAZ:

COUCH_30655

KBS:	EPA93_15280

SUS:

Acid_5654

PFER:

IRI77_02260

» show all

Reference

1 [PMID:18387946]

Authors

Luo Y, Lin S, Zhang J, Cooke HA, Bruner SD, Shen B

Title

Regiospecific O-methylation of naphthoic acids catalyzed by NcsB1, an O-methyltransferase involved in the biosynthesis of the enediyne antitumor antibiotic neocarzinostatin.

Journal

J Biol Chem 283:14694-702 (2008)
DOI:10.1074/jbc.M802206200

Sequence

[ag:AAM77984]

Reference

2 [PMID:19702337]

Authors

Cooke HA, Guenther EL, Luo Y, Shen B, Bruner SD

Title

Molecular basis of substrate promiscuity for the SAM-dependent O-methyltransferase NcsB1, involved in the biosynthesis of the enediyne antitumor antibiotic neocarzinostatin.

Journal

Biochemistry 48:9590-8 (2009)
DOI:10.1021/bi901257q

Sequence

[ag:AAM77984]

Other DBs

ExplorEnz - The Enzyme Database:

2.1.1.303

IUBMB Enzyme Nomenclature:

2.1.1.303

ExPASy - ENZYME nomenclature database:

2.1.1.303

BRENDA, the Enzyme Database:

2.1.1.303

LinkDB

REACTION: R10963

Entry

R10963                      Reaction

Name

S-adenosyl-L-methionine:2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase

Definition

S-Adenosyl-L-methionine + 2,7-Dihydroxy-5-methyl-1-naphthoate <=> S-Adenosyl-L-homocysteine + 2-Hydroxy-7-methoxy-5-methyl-1-naphthoate

Equation

C00019 + C20857 <=> C00021 + C20841

Reaction class

RC00003

C00019_C00021

RC00392

C20841_C20857

Enzyme

2.1.1.303

Pathway

rn01059

Biosynthesis of enediyne antibiotics

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00830

Neocarzinostatin naphthoate moiety biosynthesis, malonyl-CoA => 2-hydroxy-5-methyl-1-naphthoate => 2-hydroxy-7-methoxy-5-methyl-1-naphthoyl-CoA

Orthology

K20421

2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase [EC:2.1.1.303]

LinkDB

DBGET integrated database retrieval system