Monolupine (Q104394910)

(1S,9R,10R)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2,4-dien-6-one

inferred from InChI

2 references

1 reference

CID 442967

2 references

(1R,9S,10S)-7,15-Diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2,4-dien-6-one

1 reference

1 reference

inferred from InChI

chemical formula

C₁₅H₂₀N₂O

0 references

canonical SMILES

O=C1C=CC=C2N1CC3CC2CN4CCCCC43

0 references

isomeric SMILES

O=c1cccc2n1C[C@H]1C[C@@H]2CN2CCCC[C@H]12

0 references

found in taxon

Maackia amurensis

3 references

Isolation of (+)-maackiamine (norammodendrine) from the flowers of Maackia amurensis

Lupin alkaloids from Chinese Maackia amurensis

Lupin alkaloids from Chinese Maackia amurensis

Thermopsis chinensis

3 references

Isolation of a New Alkaloid (-)-0- Acetylbaptifoline and the Absolute Stereochemical Relationships of Lupine Alkaloids in Thermopsis chinensis

Absolute configuration of (+)-5,6-dehydrolupanine, a key intermediate in biosynthesis of lupin alkaloids

Analysis of lupine alkaloids in plants by high-performance liquid chromatography

Maackia tashiroi

1 reference

Tashiromine; a New Alkaloid from Maackia tashiroi

Sophora exigua

1 reference

Lupin alkaloids fromSophora exigua

Thermopsis mongolica

1 reference

13-epi-Hydroxysparteine and Desoxyangustifoline, New Alkaloids from Thermopsis mongolica

Retama raetam

3 references

(+)-12α-hydroxylupanine, a lupin alkaloid from Lygos raetam

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

Quinolizidine Alkaloid Profiles of Retama raetam, R. sphaerocarpa and R. monosperma

Anagyris foetida

2 references

Incorporation of the enantiomeric [1-2H]cadaverines into the quinolizidine alkaloid (–)- anagyrine in Anagyris foetida

Rhombifoline and 5,6-dehydrolupanine from Anagyrus foetida L

Clathrotropis glaucophylla

2 references

Quinolizidine alkaloids from the curare adjuvant Clathrotropis glaucophylla

Quinolizidine Alkaloids from the Curare Adjuvant Clathrotropis glaucophylla.

Sophora koreensis

2 references

Lupin alkaloids from flowers of Echinosophora koreensis

Lupin alkaloids from Echinosophora koreensis

Maackia tenuifolia

1 reference

A Lupin Alkaloid, (-)-Tenuamine (Norlusitanine), from Maackia tenuifolia

Sophora chrysophylla

2 references

Lupin alkaloids from sophora chrysophylla

93. Sophora alkaloids. Part III. The alkaloids of the seeds of S. chrysophylla

Dermatophyllum secundiflorum

2 references

(+)-11-oxocytisine, a lupin alkaloid from leaves of sophora secundiflora

A Qualitative and Quantitative Comparison of the Quinolizidine Alkaloids of the Fasciated and Normal Stems of Sophora secundiflora

Templetonia retusa

1 reference

Alkaloids of Templetonia retusa. Chemistry, Structure and Absolute Configuration of (-)-Templetine

Thermopsis lupinoides

4 references

Lupin alkaloids from the seeds of Thermopsis lupinoides

Alkaloids of Thermopsis Lupinoides

Alkaloids of Thermopsis Lupinoides

Analysis of lupine alkaloids in plants by high-performance liquid chromatography

Viscum cruciatum

1 reference

Quinolizidine Alkaloids fromViscum cruciatum, Hemiparasitic Shrub ofLygos sphaerocarpa

Baptisia australis var. minor

2 references

The papilionaceous alkaloids; Baptisia minor, Lehm

THE PAPILIONACEOUS ALKALOIDS: XX. LUPINUSWYETHII S. WATS. AND BAPTISIAVERSICOLOR LODD.

Baptisia perfoliata

3 references

The papilionaceous alkaloids; Baptisia perfoliata (L.) R. Br

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Genista monspessulana

1 reference

(+)-2,3-dehydro-10-oxo-alpha-isosparteine in Uresiphita reversalis larvae fed on Cytisus monspessulanus leaves

Lupinus argenteus var. laxiflorus

1 reference

Lupine Studies. XIV.1The Isolation of Anagyrine fromLupinus laxiflorusvar.silvicolaC. P. Smith

Lupinus arbustus

2 references

Lupine Studies. XIV.1The Isolation of Anagyrine fromLupinus laxiflorusvar.silvicolaC. P. Smith

Lupinus pusillus

2 references

The papilionaceous alkaloids; Lupinus pusillus, Pursh.

Alkaloid variation in the Lupinus pusillus group (Fabaceae: tribe Genisteae)

Petteria ramentacea

2 references

Quinolizidine alkaloids in petteria ramentacea and the infesting aphids, Aphis cytisorum

Quinolizidine alkaloids in Petteria ramentacea

Megaselia flavescens

2 references

(+)-12alpha-Hydroxysophocarpine, a new quinolizidine alkaloid and related anti-HBV alkaloids from Sophora flavescens

Isokuraramine and (−)-7,11-dehydromatrine, lupin alkaloids from flowers of Sophora flavescens

Sophora franchetiana

1 reference

Two cage-type lupin alkaloids from Sophora franchetiana

Sophora mollis

1 reference

Lupin alkaloids from Sophora mollis

Spartium junceum

5 references

Alkaloids from Spartium junceum growing in Georgia

Acquired toxicity ? the advantages of specializing on alkaloid-rich lupins to Macrosiphon albifrons (Aphidae)

A Survey of Alkaloids in Spartium junceum L. (Genisteae-Fabaceae)

Alkaloid content in four Spartium junceum populations as a defensive strategy against predators

Quinolizidine Alkaloids as Nitrogen Source for Lupin Seedlings and Cell Cultures

Ulex europaeus

2 references

2. The alkaloids of Ulex europaeus. Part I

Alkaloid concentration of the invasive plant species Ulex europaeus in relation to geographic origin and herbivory.

Uresiphita reversalis

1 reference

(+)-2,3-dehydro-10-oxo-alpha-isosparteine in Uresiphita reversalis larvae fed on Cytisus monspessulanus leaves

Lupinus argenteus var. argenteus

1 reference

Lupine Studies. XIV.1The Isolation of Anagyrine fromLupinus laxiflorusvar.silvicolaC. P. Smith

Lupinus argenteus

4 references

The papilionaceous alkaloids; Lupinus macounii, Rydb

Lupine Studies. XIV.1The Isolation of Anagyrine fromLupinus laxiflorusvar.silvicolaC. P. Smith

Variability of quinolizidine alkaloid profiles of Lupinus argentous (Fabaceae) from North America

Ulex jussiaei

1 reference

New quinolizidine alkaloids from cadia purpurea

Genista acanthoclada

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

Quinolizidine alkaloids inGenista acanthoclada and its holoparasite,Cuscuta palaestina

Baptisia alba

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia albescens

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia arachnifera

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia calycosa

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia cinerea

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia megacarpa

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia nuttalliana

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia simplicifolia

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia sphaerocarpa

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia tinctoria

2 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

The lupine alkaloids of the genus Baptisia (leguminosae)

Genista anglica

1 reference

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

Genista ancistrocarpa

1 reference

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

Genista tinctoria

3 references

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

Acquired toxicity ? the advantages of specializing on alkaloid-rich lupins to Macrosiphon albifrons (Aphidae)

Alkaloid Profile of Bulgarian Species from Genus Senecio L.

Gonocytisus pterocladus

1 reference

Alkaloids from Gonocytisus pterocladus

Gonocytisus angulatus

1 reference

Alkaloids from Gonocytisus pterocladus

Gonocytisus dirmilensis

1 reference

Alkaloids from Gonocytisus pterocladus

Laburnum anagyroides

2 references

Acquired toxicity ? the advantages of specializing on alkaloid-rich lupins to Macrosiphon albifrons (Aphidae)

Quinolizidine Alkaloids as Nitrogen Source for Lupin Seedlings and Cell Cultures

Lamprolobium fruticosum

1 reference

A survey of alkaloids in the genus Lamprolobium Benth. (Fabaceae: Brongniartieae)

Lamprolobium grandiflorum

1 reference

A survey of alkaloids in the genus Lamprolobium Benth. (Fabaceae: Brongniartieae)

Baptisia bracteata

1 reference

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia lanceolata

1 reference

The lupine alkaloids of the genus Baptisia (leguminosae)

Argyrolobium crassifolium

1 reference

Argyrolobium lotoides

1 reference

Argyrolobium variopile

1 reference

Polhillia pallens

1 reference

Polhillia brevicalyx

1 reference

Polhillia obsoleta

1 reference

Polhillia waltersii

1 reference

Polhillia canescens

1 reference

Polhillia connatum

1 reference

Melolobium microphyllum

1 reference

Melolobium exudans

1 reference

Melolobium aethiopicum

1 reference

Melolobium subspicatum

1 reference

Melolobium burchellii

1 reference

Melolobium wilmsii

1 reference

Melolobium stipulatum

1 reference

Melolobium canescens

1 reference

Melolobium obcordatum

1 reference

Melolobium alpinum

1 reference

Melolobium candicans

1 reference

Lupinus mutabilis

1 reference

Quinolizidine alkaloids in seeds of Lupinus mutabilis

Genista maderensis

1 reference

Quinolizidine Alkaloid Profiles of Two Taxa of Teline maderensis

Thinicola incana

1 reference

Alkaloids of Templetonia incana

Platycelyphium voensis

2 references

Quinolizidine Alkaloids of Platycelphium vöense (Engl.) Wild (Leguminosae)

Alkaloids of the genera Dicraeopetalum, Platycelyphium and Sakoanala

Platycelyphium voense

2 references

Quinolizidine Alkaloids of Platycelphium vöense (Engl.) Wild (Leguminosae)

Alkaloids of the genera Dicraeopetalum, Platycelyphium and Sakoanala

Dicraeopetalum stipulare

2 references

Quinolizidine alkaloids from the east-african legume Dicraeopetalum stipulare harms

Alkaloids of the genera Dicraeopetalum, Platycelyphium and Sakoanala

Lupinus tassilicus

1 reference

Seed alkaloid composition of Lupinus tassilicus maire (Fabaceae: Genisteae) and comparison with its related rough seeded lupin species

Lupinus pilosus

1 reference

Seed alkaloid composition of Lupinus tassilicus maire (Fabaceae: Genisteae) and comparison with its related rough seeded lupin species

Lupinus atlanticus

1 reference

Seed alkaloid composition of Lupinus tassilicus maire (Fabaceae: Genisteae) and comparison with its related rough seeded lupin species

Lupinus digitatus

1 reference

Seed alkaloid composition of Lupinus tassilicus maire (Fabaceae: Genisteae) and comparison with its related rough seeded lupin species

Lupinus palaestinus

1 reference

Seed alkaloid composition of Lupinus tassilicus maire (Fabaceae: Genisteae) and comparison with its related rough seeded lupin species

Anarthrophyllum andicolum

1 reference

The taxonomic significance of alkaloids in the South American genus Anarthrophyllum

Anarthrophyllum andicola

1 reference

The taxonomic significance of alkaloids in the South American genus Anarthrophyllum

Anarthrophyllum cumingii

1 reference

The taxonomic significance of alkaloids in the South American genus Anarthrophyllum

Anarthrophyllum elegans

1 reference

The taxonomic significance of alkaloids in the South American genus Anarthrophyllum

Anarthrophyllum rigidum

1 reference

The taxonomic significance of alkaloids in the South American genus Anarthrophyllum

Sakoanala villosa

1 reference

Alkaloids of the genera Dicraeopetalum, Platycelyphium and Sakoanala

Caulophyllum thalictroides

5 references

Gas chromatographic determination of toxic quinolizidine alkaloids in blue cohoshCaulophyllum thalictroides (L.) Michx

Analysis of aporphine and quinolizidine alkaloids from Caulophyllum thalictroides by densitometry and HPLC

Determination of saponins and alkaloids in Caulophyllum thalictroides (blue cohosh) by high-performance liquid chromatography and evaporative light scattering detection

Alkaloids and saponins from blue cohosh.

Detecting potential teratogenic alkaloids from blue cohosh rhizomes using an in vitro rat embryo culture.

Cytisus scoparius

2 references

Accumulation of quinolizidine alkaloids in plants and cell suspension cultures: genera lupinus, cytisus, baptisia, genista, laburnum, and sophora

Quinolizidine Alkaloids as Nitrogen Source for Lupin Seedlings and Cell Cultures

Chamaecytisus purpureus

1 reference

Accumulation of quinolizidine alkaloids in plants and cell suspension cultures: genera lupinus, cytisus, baptisia, genista, laburnum, and sophora

Genista canariensis

1 reference

Accumulation of quinolizidine alkaloids in plants and cell suspension cultures: genera lupinus, cytisus, baptisia, genista, laburnum, and sophora

Genista lobelii

2 references

Quinolizidine Alkaloids in Taxa ofGenista lobeliis.l. Due to the Geographical Origin Obtained by GC Analysis

Alkaloidal variation in Genista lobelii s.l. (Fabaceae)

Cuscuta palaestina

1 reference

Quinolizidine alkaloids inGenista acanthoclada and its holoparasite,Cuscuta palaestina

Plagiocarpus axillaris

1 reference

The alkaloid pattern of Plagiocarpus axillaris (Fabaceae: Brongniartieae)

Cristonia biloba

1 reference

A survey of alkaloids in Templetonia biloba (Benth.) Polhill (Fabaceae: Brongniartieae)

Lupinus flavoculatus

1 reference

Alkaloid variation in the Lupinus pusillus group (Fabaceae: tribe Genisteae)

Lupinus kingii

1 reference

Alkaloid variation in the Lupinus pusillus group (Fabaceae: tribe Genisteae)

Lupinus odoratus

1 reference

Alkaloid variation in the Lupinus pusillus group (Fabaceae: tribe Genisteae)

Lupinus luteus

1 reference

Alkaloid variation in the Lupinus pusillus group (Fabaceae: tribe Genisteae)

Lupinus shockleyi

1 reference

Alkaloid variation in the Lupinus pusillus group (Fabaceae: tribe Genisteae)

Genista ephedroides

1 reference

Quinolizidine alkaloids from Genista ephedroides

Lupinus polyphyllus

2 references

Alkaloid distribution in two species of Lupinus in central British Columbia

Lupinus arcticus

1 reference

Alkaloid distribution in two species of Lupinus in central British Columbia

Retama sphaerocarpa

1 reference

Quinolizidine Alkaloid Profiles of Retama raetam, R. sphaerocarpa and R. monosperma

Retama monosperma

1 reference

Quinolizidine Alkaloid Profiles of Retama raetam, R. sphaerocarpa and R. monosperma

Genista anatolica

2 references

Alkaloid Profile of Bulgarian Species from Genus Senecio L.

Alkaloids ofGenista anatolica

Genista carinalis

1 reference

Alkaloid Profile of Bulgarian Species from Genus Senecio L.

Genista pilosa

1 reference

Alkaloid Profile of Bulgarian Species from Genus Senecio L.

Genista subcapitata

1 reference

Alkaloid Profile of Bulgarian Species from Genus Senecio L.

Genista depressa

1 reference

Alkaloid Profile of Bulgarian Species from Genus Senecio L.

Rafnia cuneifolia

1 reference

Alkaloid Profile of Bulgarian Species from Genus Senecio L.

Osyris alba

1 reference

Concomitant occurrence of pyrrolizidine and quinolizidine alkaloids in the hemiparasite Osyris alba L. (Santalaceae)

Ormosia discolor

1 reference

Alkaloid distribution in seeds of Ormosia, Pericopsis and Haplormosia

Ormosia fordiana

1 reference

Alkaloid distribution in seeds of Ormosia, Pericopsis and Haplormosia

Ormosia panamensis

1 reference

Alkaloid distribution in seeds of Ormosia, Pericopsis and Haplormosia

Ormosia sumatrana

1 reference

Alkaloid distribution in seeds of Ormosia, Pericopsis and Haplormosia

Pericopsis angolensis

1 reference

Alkaloid distribution in seeds of Ormosia, Pericopsis and Haplormosia

Haplormosia monophylla

1 reference

Alkaloid distribution in seeds of Ormosia, Pericopsis and Haplormosia

Genista cinerascens

1 reference

Distribution and taxonomic significance of alkaloids in the Genista cinerea agregat

Genista cinerea

1 reference

Distribution and taxonomic significance of alkaloids in the Genista cinerea agregat

Genista majorica

1 reference

Distribution and taxonomic significance of alkaloids in the Genista cinerea agregat

Clathrotropis brachypetala

1 reference

Quinolizidine Alkaloids of Clathrotropis brachypetala

Genista libanotica

1 reference

Alkaloids of Genista libanotica

Thermopsis turcica

1 reference

Sophazrine--a Novel Quinolizidine Alkaloid from Sophora griffithii

Vuralia turcica

1 reference

Sophazrine--a Novel Quinolizidine Alkaloid from Sophora griffithii

Oxytropis ochrocephala

1 reference

Quinolizidine alkaloids from Oxytropis ochrocephala

Ammodendron karelinii

2 references

Alkaloids of Ammodendron karelinii

Biosyntheis of the alkaloids of Ammodendron karelinii

Bolusanthus speciosus

1 reference

Alkaloids of Bolusanthus speciosus

Genista burdurensis

1 reference

Alkaloids of Genista burdurensis

Chamaecytisus eriocarpus

1 reference

Flavonoids and Alkaloids from Chamaecytisus eriocarpus

Dichilus strictus

1 reference

Chemotaxonomic value of alkaloids in the genus Dichilus

Dichilus reflexus

1 reference

Chemotaxonomic value of alkaloids in the genus Dichilus

Dichilus lebeckioides

1 reference

Chemotaxonomic value of alkaloids in the genus Dichilus

Dichilus pilosus

1 reference

Chemotaxonomic value of alkaloids in the genus Dichilus

Dichilus gracilis

1 reference

Chemotaxonomic value of alkaloids in the genus Dichilus

Lupinus leucophyllus

1 reference

Lupinus littoralis

1 reference

Lupinus sericeus

1 reference

Lupinus albicaulis

1 reference

Lupinus albifrons

1 reference

Lupinus andersonii

1 reference

Lupinus bicolor

1 reference

Lupinus concinnus

1 reference

Lupinus evermannii

1 reference

Lupinus hirsutissimus

1 reference

Lupinus latifolius

1 reference

Lupinus nootkatensis

1 reference

Lupinus rivularis

1 reference

Lupinus subcarnosus

1 reference

Biosynthesis of quinolizidine alkaloids in lupine species

Lupinus cosentinii

1 reference

Seed alkaloid composition of Lupinus tassilicus maire (Fabaceae: Genisteae) and comparison with its related rough seeded lupin species

Anarthrophyllum desideratum

1 reference

The taxonomic significance of alkaloids in the South American genus Anarthrophyllum

Baptisia bracteata var. laevicaulis

1 reference

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

Baptisia lanceolata var. elliptica

1 reference

The lupine alkaloids of the genus Baptisia (leguminosae)

Baptisia lactea var. pendula

1 reference

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

Baptisia lactea var. lactea

2 references

The lupine alkaloids of the genus Baptisia (leguminosae)

Alkaloid-Bearing Plants and Their Contained Alkaloids. 1957-1968

Lupinus lepidus var. aridus

1 reference

Lupinus argenteus var. rubricaulis

1 reference

Lupinus microcarpus var. microcarpus

1 reference

Lupinus polyphyllus var. burkei

1 reference

Lupinus polyphyllus var. humicola

1 reference

Lupinus nanus

1 reference

Alkaloid variation in the Lupinus pusillus group (Fabaceae: tribe Genisteae)

Lupinus holosericeus

1 reference

Alkaloid Variation in Lupinus holosericeus

Genista salzmannii

2 references

Quinolizidine Alkaloids in Taxa ofGenista lobeliis.l. Due to the Geographical Origin Obtained by GC Analysis

Alkaloidal variation in Genista lobelii s.l. (Fabaceae)

Lupinus gredensis

1 reference

Lupinus hispanicus

1 reference

Lupinus hybridus

1 reference

Sophora flavescens

1 reference

Nematicidal activities of (-)-N-meth-ylcytisine and (-)-anagyrine from sophora flavescens against pine wood nematodes.

Thermopsis lanceolata

3 references

Alkaloids of Thermopsis Lupinoides

Analysis of lupine alkaloids in plants by high-performance liquid chromatography

Lupin alkaloids from the seeds of Thermopsis lupinoides

Identifiers

InChI

InChI=1S/C15H20N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h3,5-6,11-13H,1-2,4,7-10H2/t11-,12-,13-/m1/s1

0 references

InChIKey

FQEQMASDZFXSJI-JHJVBQTASA-N

0 references

CAS Registry Number

486-89-5

1 reference

CAS (formerly Chemical Abstracts Service)

25 January 2022

1 reference

17 September 2022