(Q6122828)

Gene Ontology release 2019-11-16

(S)-reticuline biosynthetic process

subject has role

product

1 reference

Gene Ontology release 2019-11-16

chemical structure

Reticuline.png
1,057 × 678; 12 KB

0 references

mass

329.16270821599994 dalton

1 reference

based on heuristic

inferred from isomeric SMILES

1 reference

C₁₉H₂₃NO₄

1 reference

PubChem

canonical SMILES

OC1=CC(=CC=C1OC)CC2C3=CC(O)=C(OC)C=C3CCN2C

0 references

isomeric SMILES

CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC

2 references

3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase

1 reference

25 February 2021

1 reference

Radioimmunoassay determination of six opium alkaloids and its application to plant screening

Papaver cylindricum

1 reference

Radioimmunoassay determination of six opium alkaloids and its application to plant screening

Papaver gracile

1 reference

Radioimmunoassay determination of six opium alkaloids and its application to plant screening

Papaver persicum

1 reference

Radioimmunoassay determination of six opium alkaloids and its application to plant screening

Papaver somniferum

1 reference

Radioimmunoassay determination of six opium alkaloids and its application to plant screening

Magnolia biondii

1 reference

Neuromuscular Blocking Action of Alkaloids from a Japanese Crude Drug “Shin-I” (Flos Magnoliae) in Frog Skeletal Muscle

Croton hemiargyreus

1 reference

Identification of Isoquinoline alkaloids in crude extracts by high temperature gas chromatography-mass spectrometry

Aniba canelilla

1 reference

Nouveaux alcaloïdes isoquinoléiques isolés d'une Lauraceae bolivienne: Aniba canelilla H.B.K.

Annona purpurea

2 references

New alkaloids from Annona purpurea

Four alkaloids from Annona cherimola.

Annona reticulata

2 references

Chemistry in the Annonaceae, XXII. 14-Hydroxy-25-desoxyrollinicin from the Stem Bark of Annona reticulata

Revision of the early steps of reticuline biosynthesis

Annona spinescens

1 reference

Pessoine and spinosine, two catecholic berbines from Annona spinescens

Aristolochia gigantea

1 reference

Aristolactams and Alkamides of Aristolochia gigantea.

Artabotrys hexapetalus

1 reference

The alkaloids of Artabotrys uncinatus.

Berberis brandisiana

1 reference

Berbamine 2'-β-N-oxide, a New Bisbenzylisoquinoline from Berberis brandisiana

Berberis heterobotrys

1 reference

1 reference

Aporphine alkaloids from Clematis parviloba and their antifungal activity

Croton celtidifolius

1 reference

Alkaloids of Croton celtidifolius

Delphinium pentagynum

1 reference

Alkaloids from Delphinium pentagynum

Guatteria goudotiana

1 reference

Alkaloids from Guatteria goudotiana

Isopyrum thalictroides

1 reference

Alkaloids from Isopyrum thalictroides L

Litsea cubeba

2 references

Litebamine, a novel phenanthrene alkaloid from Litsea cubeba

Application of centrifugal partition chromatography to the separation of Lauraceous alkaloids

Miliusa velutina

1 reference

Alakaloids from the stem bark of Miliusa velutina

Monocyclanthus vignei

1 reference

6a,7-Dehydro-2-hydroxy-4,5-dioxonoraporphine and Other Alkaloids from Monocyclanthus vignei:13C-nmr Studies on 4,5-Dioxoaporphines

Neolitsea acuminatissima

1 reference

Cytotoxic constituents of the stem bark of Neolitsea acuminatissima

Neolitsea konishii

1 reference

Isoquinoline Alkaloids from Neolitsea Konishii

Ocotea velloziana

1 reference

Benzylisoquinoline alkaloids and flavonols from Ocotea vellosiana

Orophea hexandra

1 reference

Alkaloids from Orophea hexandra

Hubera cerasoides

1 reference

Bioactive constituents of the roots of Polyalthia cerasoides

Porcelia macrocarpa

2 references

Alkaloids from Porcelia macrocarpa.

Alkaloids From Fumaria macrocarpa

Annona emarginata

1 reference

Alkaloids from Rollinia emarginata

Siparuna grandiflora

1 reference

Alkaloids of Siparuna tonduziana

Xylopia holtzii

1 reference

Secondary and tertiary isoquinoline alkaloids from Xylopia parviflora

Aconitum seravschanicum

2 references

Alkaloids of Aconitum ferox

Alkaloids ofAconitum zeravschanicum

Aniba muca

1 reference

Alkaloids from Gelsemium elegans

Annona cherimola

1 reference

Alkaloids from Annona cherimolia Leaves

Annona salzmannii

1 reference

Antimicrobial activity of benzylisoquinoline alkaloids from Annona salzmanii D.C

Arctomecon humile

1 reference

Alkaloids of Arctomecon species (Papaveraceae). 12-methoxyallocryptopine, a new protopine-type alkaloid

1 reference

1 reference

Artabotrys monteiroae

1 reference

Ion-pair and ion-suppression high performance liquid chromatographic analysis of alkaloidal constituents ofArtabotrys monteiroae

Artabotrys venustus

1 reference

Artavenustine, a Catecholic Berbine from Artabotrys venustus

Berberis heteropoda

3 references

Berberis alkaloids. XVI. Structure of berpodine

Berberis alkaloids XIII. An investigation of the alkaloids of Berberis heteropoda

Berberis alkaloids. XVII. Investigation of the alkaloids of Berberis heteropoda

Berberis

1 reference

S-adenosyl-l-methionine: 3′-hydroxy-N-methyl-(S)-coclaurine-4′-O-methyl transferase, a regio- and stereoselective enzyme of the (S)-reticuline pathway

Berberis nummularia

1 reference

Berberis alkaloids. XXV. Structures of bernumidine and bernumicine

Berberis stolonifera

2 references

A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline alkaloid reticuline

The hydroxylation step in the biosynthetic pathway leading from norcoclaurine to reticuline

Bongardia chrysogonum

1 reference

An Investigation of Bongardia chrysogonum

Coptis japonica

1 reference

Molecular characterization of the S-adenosyl-L-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase involved in isoquinoline alkaloid biosynthesis in Coptis japonica.

Corydalis caucasica

1 reference

Spirobenzylisoquinoline Alkaloids from Corydalis caucasica

Corydalis gortschakovii

1 reference

Alkaloids ofCorydalis gortschakovii

Corydalis pseudoadunca

1 reference

Alkaloids ofCorydalis pseudoadunca

Corydalis rutifolia

1 reference

Minor Alkaloids of Corydalis rutifolia (Sibth. and Sm.) D. C. subsp. kurdica Cullen and Davis of Turkish Origin

Cryptocarya griffithiana var. crassinervia

1 reference

New phenantrene alkaloids from Cryptocarya crassinervia

Cymbopetalum brasiliense

1 reference

Alkaloids from Annonaceae; LV1. Chemistry and Pharmacology ofCymbopetalum brasiliense

Dehaasia hainanensis

1 reference

Isoquinoline Alkaloids from the Leaves of Dehaasia Hainanensis

Dicentra peregrina

1 reference

Nerium species Oleander

Eschscholzia californica

1 reference

A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline alkaloid reticuline

Fumaria capreolata

1 reference

Isoquinoline alkaloids from cell suspension cultures of Fumaria capreolata

Few-flower fumitory, Earthsmoke

2 references

Alkaloids ofFumaria vaillantii

Alkaloids of Fumaria vaillantii

Glaucium corniculatum

2 references

Minor alkaloids of Glaucium flavum

Alkaloids ofGlaucium corniculatum

Glaucium fimbrilligerum

3 references

Alkaloids of Glaucium fimbrilligerum

Alkaloids ofGlaucium fimbrilligerum. II

Alkaloids ofGlaucium fimbrilligerum

Glaucium flavum

1 reference

Alkaloids ofGlaucium flavium

Glossocalyx brevipes

1 reference

(+)-N-Methyllaurotetanine-β-N-Oxide from Glossocalyx brevipes

Guatteria juruensis

1 reference

Alkaloids and volatile constituents from Guatteria juruensis

Gyrocarpus americanus

1 reference

Alcaloïdes de Gyrocarpus americanus

Hernandia cordigera

1 reference

Structure of aconifine

Hernandia nymphaeifolia

2 references

Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia

New aporphine alkaloids and cytotoxic constituents of Hernandia nymphaeifolia

Laurobasidium lauri

2 references

Sesquiterpene lactones from Carpesium divaricatum

Uterine inhibitory effect of reticuline

Leontice leontopetalum

1 reference

Chemical Constituents of the Flora of Jordan, II. Alkaloids of Leontic leontopetalum

Leptadenia reticulata

1 reference

Three Novel Pregnane Glycosides from Leptadenia reticulata Wight and Arn.

Lindera glauca

1 reference

Alkaloids From Lindera glauca, Lindera erythrocarpa, and Lindera citriodora

Lindera megaphylla

1 reference

Northalifoline, a New Isoquinolone Alkaloid from the Pedicels of Lindera megaphylla

Litsea elliptica

1 reference

The Constituents of the Bark of Litsea elliptica (Lauraceae)

Litsea lecardii

1 reference

Plants of New Caledonia Part 103.1Alkaloids ofLitsea lecardii

Magnolia salicifolia

2 references

Anti-Inflammatory Effect of Neolignans Newly Isolated from the Crude Drug "Shin-i" (Flos Magnoliae)

Neuromuscular Blocking Action of Alkaloids from a Japanese Crude Drug “Shin-I” (Flos Magnoliae) in Frog Skeletal Muscle

Monodora junodii

1 reference

Secondary and tertiary isoquinoline alkaloids from Xylopia parviflora

Neolitsea aciculata

1 reference

Alkaloids From Neolitsea aciculata

Ocotea duckei

1 reference

Central depressant effects of reticuline extracted from Ocotea duckei in rats and mice

Oxandra major

1 reference

Azafluorenones from Oxandra cf. major and biogenetic considerations☆

Pachygone ovata

1 reference

Constituents of Pachygone ovata and Pharmacological Action of its Major Leaf Alkaloid

árnica

1 reference

A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline alkaloid reticuline

Phoebe formosana

1 reference

Application of centrifugal partition chromatography to the separation of Lauraceous alkaloids

Ocotea pittieri

1 reference

Chemical and Biological Extractives of Lauraceae Species in Costa Rican Tropical Forests

Stephania cephalantha

2 references

Alkaloidal Constituents of the Tubers of Stephania cepharantha Cultivated in Japan: Structure of 3,4-Dehydrocycleanine, a New Bisbenzylisoquinoline Alkaloid.

Alkaloidal Constituents of the Leaves of Stephania cepharantha Cultivated in Japan: Structure of Cephasugine, a New Morphinane Alkaloid.

Stephania pierrei

3 references

New Bisbenzylisoquinolines from Stephania pierrii

Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei

Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei

Stephania venosa

1 reference

Some Unusual Proaporphine and Aporphine Alkaloids from Stephania venosa

Thalictrum foliolosum

1 reference

The Alkaloids of Thalictrum foliolosum

Thalictrum pedunculatum

1 reference

A New Pentasubstituted Aporphine: (+)-N-Methyldanguyelline

Xylopia papuana

1 reference

Dopaminergic Isoquinoline Alkaloids from Roots ofXylopia papuana

Annona glabra

2 references

Characterization of Acetylcholinesterase Inhibitory Constituents from Annona glabra Assisted by HPLC Microfractionation

Annoglabayin, a novel dimeric kaurane diterpenoid, and apoptosis in Hep G2 cells of annomontacin from the fruits of Annona glabra

Corydalis ternata

1 reference

Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity

Hypserpa nitida

1 reference

Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida

Cissampelos capensis

1 reference

Alkaloidal variation in cissampelos capensis (Menispermaceae).

Corydalis orthopoda

1 reference

[Studies on the alkaloids of papaveraceous plants. XIX. Alkaloids of Corydalis koidzumiana Ohwi (author's transl)]

Corydalis taliensis

1 reference

Isoquinoline Alkaloids from Corydalis taliensis

Erythrina variegata

1 reference

Studies on the Erythrina Alkaloids. V. Alkaloids of Erythrina crystagalli (L.) cv. Maruba Deiko H. MURATA

Litsea lancifolia

1 reference

Lancifoliaine, a new bisbenzylisoquinoline from the bark of Litsea lancifolia

Magnolia officinalis

2 references

A novel aporphine alkaloid from Magnolia officinalis

Studies on the alkaloids of the bark of Magnolia officinalis: isolation and on-line analysis by HPLC-ESI-MS(n).

Siparuna apiosyce

1 reference

Kaempferol glycosides from Siparuna apiosyce

Stephania viridiflavens

1 reference

Novel N-oxide derivatives of benzyltetrahydroisoquinoline alkaloid from the tubers of Stephania viridiflavens H.S. Lo et M. Yang

Damburneya salicifolia

1 reference

Costaricine, a new antiplasmodial bisbenzylisoquinoline alkaloid from Nectandra salicifolia trunk bark

Siparuna brasiliensis

1 reference

Kaempferol glycosides from Siparuna apiosyce

Anomianthus dulcis

1 reference

Alkaloids from Anomianthus dulcis

Xylopia laevigata

1 reference

Cytotoxic Alkaloids from the Stem of Xylopia laevigata.

Ocotea fasciculata

1 reference

Central depressant effects of reticuline extracted from Ocotea duckei in rats and mice

Oxandra xylopioides

1 reference

Azafluorenones from Oxandra cf. major and biogenetic considerations☆

Ceratocapnos turbinata

1 reference

Some C-Secocularines from Ceratocapnos palaestinus

Arctomecon humilis

1 reference

Alkaloids of Arctomecon species (Papaveraceae). 12-methoxyallocryptopine, a new protopine-type alkaloid

Argemone mexicana

1 reference

Cytotoxic benzophenanthridine and benzylisoquinoline alkaloids from Argemone mexicana.

Lindera pulcherrima var. hemsleyana

1 reference

Separation and quantitative determination of sesquiterpene lactones in Lindera aggregata (wu-yao) by ultra-performance LC-MS/MS.

Thalictrum tuberosum

1 reference

Metabolism of (S)-reticuline in an alkaloid non-producing cell culture strain of Thalictrum tuberosum

Papaver arenarium

1 reference

Radioimmunoassay determination of six opium alkaloids and its application to plant screening

Cananga odorata

1 reference

The Constituents ofCananga odorata

Corydalis uniflora

1 reference

Minor Alkaloids of Corydalis rutifolia (Sibth. and Sm.) D. C. subsp. kurdica Cullen and Davis of Turkish Origin

2 references

Berberis alkaloids XXXII. Berberal — A new alkaloid fromBerberis heterobotrys

Glossocalyx longicuspis

1 reference

(+)-N-Methyllaurotetanine-β-N-Oxide from Glossocalyx brevipes

Guatteria hirsuta

1 reference

Alkaloids and volatile constituents from Guatteria juruensis

Actinodaphne acuminata

1 reference

Two New Isoquinoline Alkaloids from Litsea cubeba

Actinodaphne longifolia

1 reference

Two New Isoquinoline Alkaloids from Litsea cubeba

Papaver armeniacum

1 reference

Radioimmunoassay determination of six opium alkaloids and its application to plant screening

Berberis integerrima

3 references

Berberis alkaloids XXXII. Berberal — A new alkaloid fromBerberis heterobotrys

Berberis alkaloids. XXII. Interbrinine and intebrimine ? New alkaloids from Berberis integerrima

1 reference

Alkaloids of Papaver fugax

Greenwayodendron oliveri

1 reference

A Spectral Method for the Determination of the Position of a Phenolic Group on Ring A of an Aporphine. Four New Aporphines From Polyalthia acuminata

Laureliopsis philippiana

1 reference

Additional alkaloids from Laurelia philippiana and L. novae-zelandiae

Enicosanthum acuminatum

1 reference

A Spectral Method for the Determination of the Position of a Phenolic Group on Ring A of an Aporphine. Four New Aporphines From Polyalthia acuminata

Cananga brandisiana

1 reference

Targeted isolation of natural analogs of anti-mycobacterial hit compounds based on the metabolite profiling of a large collection of plant extracts

Annona muricata

5 references

Novel cytotoxic annonaceous acetogenins from Annona muricata

New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata

Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata

Cohibins C and D, two important metabolites in the biogenesis of acetogenins from Annona muricata and Annona nutans

Annona muricata (Annonaceae): A Review of Its Traditional Uses, Isolated Acetogenins and Biological Activities

Thalictrum flavum

1 reference

Structural and Functional Studies of Pavine N-Methyltransferase from Thalictrum flavum Reveal Novel Insights into Substrate Recognition and Catalytic Mechanism

Commons category

Reticuline

0 references

Identifiers

InChI

InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1

1 reference

PubChem

2 references

PubChem

ChEBI release 2020-09-01

CAS Registry Number

485-19-8

1 reference

https://commonchemistry.cas.org/detail?cas_rn=485-19-8

9 April 2021

ChemSpider ID

388724

1 reference

English Wikipedia

PubChem CID

439653

2 references

English Wikipedia

Reaxys registry number

95671

0 references

ChEBI ID

16718

mapping relation type

exact match

1 reference

International Chemical Identifier

InChI

InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1

ChEMBL ID

CHEMBL401501

1 reference

2 references

inferred from InChIKey

splash10-0006-0912000000-65ae017c9708fdd8cf63

1 reference

0 references

DSSTox substance ID

DTXSID001317199

1 reference

EC number

207-611-3

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.006.920

retrieved

27 December 2018

title

(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol (English)

quotation

CAS no.: 485-19-8 (English)

ECHA Substance Infocard ID

100.006.920

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.006.920

retrieved

27 December 2018

title

(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol (English)

quotation

CAS no.: 485-19-8 (English)

Human Metabolome Database ID

HMDB0003601

2 references

based on heuristic

inferred from InChIKey

0 references

1 reference