Liriodenine (BioDeep_00000326798)

natural product PANOMIX_OTCML-2023

代谢物信息卡片

3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6.0^{8,20.0^{14,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one

化学式: C17H9NO3 (275.0582404)
中文名称: 鹅掌楸碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1ccc2c(c1)c1c3c(ccnc3C2=O)cc2c1OCO2
InChI: InChI=1/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2

描述信息

Liriodenine is an oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities. It has a role as a metabolite, an antineoplastic agent, an antimicrobial agent, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.2.1.20 (alpha-glucosidase) inhibitor and an antifungal agent. It is a cyclic ketone, an oxacycle, an organic heteropentacyclic compound, an alkaloid antibiotic and an oxoaporphine alkaloid. It is functionally related to an aporphine.
Liriodenine is a natural product found in Magnolia mexicana, Annona purpurea, and other organisms with data available.
An oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities.

同义名列表

22 个代谢物同义名

3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6.0^{8,20.0^{14,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one; 3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one; Noraporphin-7-one, 4,5,6,6a-tetradehydro-1,2-(methylenedioxy)-; Noraporphin-7-one,5,6,6a-tetradehydro-1,2-(methylenedioxy)-; 8H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one #; 8H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one; 8H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-8-one; 8H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-8-one; 4-27-00-06585 (Beilstein Handbook Reference); 8H-Benzo[g]-1,5,4-de]quinolin-8-one; Ushinsunine, oxo-; Spermatheridine; Spermatheridin; Oxoushinsunine; Oxoushinsunin; MEGxp0_001521; NCI60_042088; NCI60_001798; Liriodenine; Hiriodenine; Micheline B; 8H-Benzo[g]-1,3benzodioxolo[6,5,4-de]quinolin-8-one

数据库引用编号

20 个数据库交叉引用编号

ChEBI: CHEBI:70649
KEGG: C09567
PubChem: 10144
ChEMBL: CHEMBL37736
Wikipedia: Liriodenine
MeSH: liriodenine
ChemIDplus: 0000475752
CAS: 475-75-2
MoNA: CCMSLIB00000224030
MoNA: PM013511
medchemexpress: HY-N3376
PMhub: MS000233498
PMhub: MS000164400
PMhub: MS000112573
MetaboLights: MTBLC70649
PubChem: 11758
KNApSAcK: C00001878
3DMET: B03087
NIKKAJI: J12.552K
RefMet: Liriodenine

分类词条

Aporphine alkaloids

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

268 个相关的物种来源信息

49314 Annona cherimola:
85872 Magnolia compressa:
74884 Doryphora sassafras: 10.2307/4117899
84873 Chelonanthus albus:
3415 Liriodendron tulipifera:
354528 Zanthoxylum nitidum:
1123437 Annona purpurea:
2803928 Neolitsea acuminatissima: 10.1021/NP010236W
1937577 Annona ambotay: 10.1016/S0031-9422(00)83902-3
4432 Nelumbo nucifera:
301693 Annona squamosa:
349509 Magnolia obovata:
74946 Illigera luzonensis: 10.1021/NP9700735
493334 Monodora junodii: 10.1016/J.PHYTOCHEM.2006.07.011
1345219 Beilschmiedia alloiophylla: 10.1016/J.FITOTE.2011.11.009
74887 Laurelia novae-zelandiae: 10.1021/NP50033A032
152363 Sinomenium acutum:
63801 Ocotea: 10.1007/978-1-4899-1783-6_3
128687 Phoebe formosana:
301699 Annona mucosa:
301862 Annona reticulata:
54732 Magnolia kobus:
3406 Magnolia grandiflora:
1602035 Goniothalamus amuyon:
63805 Glossocalyx longicuspis:
1317845 Glossocalyx brevipes:
296858 Greenwayodendron oliveri:
2025453 Cardiopetalum calophyllum: 10.1055/S-2006-960213
1891178 Annickia polycarpa: 10.1055/S-0028-1097597
306945 Annona senegalensis: 10.1007/S10600-013-0683-0
461616 Pachygone ovata:
690737 Disepalum pulchrum: 10.1016/0031-9422(90)85344-F
235812 Polyalthia stenopetala:
3411 Magnolia salicifolia: 10.1055/S-2007-969493
296847 Fissistigma glaucescens:
513648 Pseuduvaria trimera: 10.1016/0031-9422(88)83076-0
1679246 Pseuduvaria indochinensis: 10.1016/0031-9422(88)83076-0
225833 Artabotrys hexapetalus:
2072219 Annona neosericea: 10.1021/NP50027A028
1202398 Dasymaschalon longiflorum: 10.1016/S0031-9422(00)91254-8
88856 Atherosperma moschatum:
2651907 Artabotrys zeylanicus: 10.1016/0031-9422(96)00181-1
489335 Lettowianthus stellatus: 10.1016/S0031-9422(00)00012-1
301703 Annona glabra:
1937578 Annona foetida: 10.1021/NP050422S
402569 Guatteria friesiana:
13393 Cananga odorata:
63813 Siparuna brasiliensis: 10.1016/S0031-9422(00)00222-3
1317910 Xylopia aethiopica:
493319 Isolona congolana: 10.1016/0031-9422(95)00333-3
493324 Isolona maitlandii: 10.1016/0031-9422(95)00333-3
489330 Hexalobus crispiflorus: 10.1002/JLAC.198219820905
992712 Hexalobus monopetalus: 10.1055/S-2006-962386
2708762 Cleistopholis patens:
2743202 Annona spinescens: 10.1021/NP960223W
1569033 Unonopsis spectabilis: 10.1021/NP50057A017
2516453 Stephania corymbosa: 10.1016/S0031-9422(00)83953-9
13521 Eupomatia bennettii: 10.1071/CH9911615
402568 Guatteria blepharophylla:
12953 Asimina triloba:
235764 Mitrephora maingayi: 10.1016/J.BSE.2007.01.011
1489755 Mitrephora tomentosa: 10.1002/HLCA.200890109
1679250 Mitrephora thorelii: 10.1002/HLCA.200890109
1310105 Polyalthia insignis:
2306826 Polyalthia microtus: 10.1016/S0040-4039(97)00051-8
1310093 Monoon borneense:
1504475 Phaeanthus ophthalmicus:
1504478 Polyalthia macropoda:
197124 Microcos paniculata: 10.1021/NP3007414
2027493 Friesodielsia velutina: 10.1016/S0031-9422(00)95214-2
85864 Magnolia officinalis: 10.1016/J.FITOTE.2011.01.021
34247 Desfontainia spinosa: 10.1016/S0031-9422(00)81172-3
86770 Magnolia odora:
49863 Eupomatia laurina:
580318 Mitrephora glabra: 10.1021/NP900572G
1766670 Disepalum anomalum: 10.1080/10575639608044938
2709017 Uvaria mocoli: 10.1016/S0031-9422(98)80009-5
235752 Miliusa horsfieldii: 10.1055/S-2002-33804
235744 Meiogyne virgata: 10.1016/S0031-9422(00)81449-1
1129707 Sapranthus palanga: 10.1016/S0031-9422(00)81171-1
2054587 Unonopsis guatterioides: 10.1002/(SICI)1099-1573(199903)13:2<175::AID-PTR395>3.0.CO;2-N
235751 Miliusa cuneata:
235758 Miliusa velutina: 10.1016/S0305-1978(99)00083-6
306934 Oxandra xylopioides:
328402 Zanthoxylum simulans: 10.1021/NP50111A003
1267437 Meiogyne monosperma: 10.1021/NP50062A009
174980 Uvaria rufa: 10.1007/S10600-011-9970-9
306973 Monodora tenuifolia: 10.1055/S-2007-969768
177463 Eulimella: 10.1055/S-2006-962040
295174 Guatteria megalophylla: 10.1021/NP50022A021
2895535 Limaciopsis loangensis: 10.1055/S-0028-1097180
295183 Guatteria punctata: 10.1021/NP50048A018
128258 Magnolia elegans: 10.1016/0031-9422(92)83308-L
86754 Magnolia baillonii: 10.1021/NP50053A020
49857 Annona montana: 10.1016/0031-9422(93)85547-5
235830 Pseuduvaria rugosa: 10.1248/CPB.59.896
527508 Stephania venosa: 10.1021/NP50040A028
461624 Rhigiocarya racemifera: 10.1021/NP50007A010
235797 Huberantha cerasoides: 10.1007/S11418-007-0138-7
295178 Guatteria oliviformis:
295164 Guatteria guianensis: 10.1021/NP0200717
295175 Guatteria multivenia: 10.1021/NP0200717
402570 Guatteria hispida: 10.1021/NP100013R
1129538 Annona papilionella: 10.1021/NP50027A027
681406 Annona acuminata: 10.1021/NP50019A011
235846 Trivalvaria macrophylla: 10.1021/NP50070A013
343279 Guatteria modesta: 10.1021/NP50032A036
86772 Magnolia lanuginosa:
1310094 Monoon cupulare: 10.1080/14786411003774338
261083 Goniothalamus scortechinii: 10.3109/13880208909053943
261087 Goniothalamus tapis: 10.3109/13880208909053943
172644 Broussonetia papyrifera: 10.1007/S10600-007-0042-0
327930 Thalictrum javanicum: 10.1016/0031-9422(88)80247-4
79563 Chydenanthus excelsus: 10.1016/0031-9422(73)85146-5
86759 Magnolia doltsopa: 10.1016/0031-9422(73)85146-5
86726 Magnolia cathcartii: 10.1016/0031-9422(73)85146-5
2029787 Annona emarginata: 10.1055/S-1999-13961
673196 Uvaria versicolor: 10.1002/PTR.1158
343270 Guatteria amplifolia: 10.1016/J.BSE.2011.03.001
306925 Oxandra asbeckii: 10.1021/NP50084A001
74957 Siparuna guianensis: 10.1016/0031-9422(76)85135-7
86757 Magnolia champaca:
111569 Magnolia mexicana:
85854 Magnolia coco:
1267443 Trivalvaria costata: 10.1002/HLCA.200790080
2072264 Mollinedia gilgiana: 10.1002/PCA.584
765229 Mollinedia schottiana: 10.1002/PCA.584
128655 Neolitsea sericea: 10.1248/YAKUSHI1947.86.2_129
344079 Litsea sericea: 10.1248/YAKUSHI1947.86.2_129
85861 Magnolia liliifera: 10.1021/NP50072A043
1631845 Annona macroprophyllata: 10.1080/14786419.2010.533373
74959 Siparuna thecaphora: 10.1016/0031-9422(86)80080-2
497606 Goniothalamus cheliensis: 10.1016/J.CCLET.2008.01.007
672953 Uvaria argentea: 10.1002/PTR.1318
49314 Annona cherimola:
85872 Magnolia compressa:
74884 Doryphora sassafras: 10.2307/4117899
84873 Chelonanthus albus:
3415 Liriodendron tulipifera:
354528 Zanthoxylum nitidum:
1123437 Annona purpurea:
2803928 Neolitsea acuminatissima: 10.1021/NP010236W
1937577 Annona ambotay: 10.1016/S0031-9422(00)83902-3
4432 Nelumbo nucifera:
301693 Annona squamosa:
349509 Magnolia obovata:
74946 Illigera luzonensis: 10.1021/NP9700735
493334 Monodora junodii: 10.1016/J.PHYTOCHEM.2006.07.011
1345219 Beilschmiedia alloiophylla: 10.1016/J.FITOTE.2011.11.009
74887 Laurelia novae-zelandiae: 10.1021/NP50033A032
152363 Sinomenium acutum:
63801 Ocotea: 10.1007/978-1-4899-1783-6_3
128687 Phoebe formosana:
301699 Annona mucosa:
301862 Annona reticulata:
54732 Magnolia kobus:
3406 Magnolia grandiflora:
1602035 Goniothalamus amuyon:
63805 Glossocalyx longicuspis:
1317845 Glossocalyx brevipes:
296858 Greenwayodendron oliveri:
2025453 Cardiopetalum calophyllum: 10.1055/S-2006-960213
1891178 Annickia polycarpa: 10.1055/S-0028-1097597
306945 Annona senegalensis: 10.1007/S10600-013-0683-0
461616 Pachygone ovata:
690737 Disepalum pulchrum: 10.1016/0031-9422(90)85344-F
235812 Polyalthia stenopetala:
3411 Magnolia salicifolia: 10.1055/S-2007-969493
296847 Fissistigma glaucescens:
513648 Pseuduvaria trimera: 10.1016/0031-9422(88)83076-0
1679246 Pseuduvaria indochinensis: 10.1016/0031-9422(88)83076-0
225833 Artabotrys hexapetalus:
2072219 Annona neosericea: 10.1021/NP50027A028
1202398 Dasymaschalon longiflorum: 10.1016/S0031-9422(00)91254-8
88856 Atherosperma moschatum:
2651907 Artabotrys zeylanicus: 10.1016/0031-9422(96)00181-1
489335 Lettowianthus stellatus: 10.1016/S0031-9422(00)00012-1
301703 Annona glabra:
1937578 Annona foetida: 10.1021/NP050422S
402569 Guatteria friesiana:
13393 Cananga odorata:
63813 Siparuna brasiliensis: 10.1016/S0031-9422(00)00222-3
1317910 Xylopia aethiopica:
493319 Isolona congolana: 10.1016/0031-9422(95)00333-3
493324 Isolona maitlandii: 10.1016/0031-9422(95)00333-3
489330 Hexalobus crispiflorus: 10.1002/JLAC.198219820905
992712 Hexalobus monopetalus: 10.1055/S-2006-962386
2708762 Cleistopholis patens:
2743202 Annona spinescens: 10.1021/NP960223W
1569033 Unonopsis spectabilis: 10.1021/NP50057A017
2516453 Stephania corymbosa: 10.1016/S0031-9422(00)83953-9
13521 Eupomatia bennettii: 10.1071/CH9911615
402568 Guatteria blepharophylla:
12953 Asimina triloba:
235764 Mitrephora maingayi: 10.1016/J.BSE.2007.01.011
1489755 Mitrephora tomentosa: 10.1002/HLCA.200890109
1679250 Mitrephora thorelii: 10.1002/HLCA.200890109
1310105 Polyalthia insignis:
2306826 Polyalthia microtus: 10.1016/S0040-4039(97)00051-8
1310093 Monoon borneense:
1504475 Phaeanthus ophthalmicus:
1504478 Polyalthia macropoda:
197124 Microcos paniculata: 10.1021/NP3007414
2027493 Friesodielsia velutina: 10.1016/S0031-9422(00)95214-2
85864 Magnolia officinalis: 10.1016/J.FITOTE.2011.01.021
34247 Desfontainia spinosa: 10.1016/S0031-9422(00)81172-3
86770 Magnolia odora:
49863 Eupomatia laurina:
580318 Mitrephora glabra: 10.1021/NP900572G
1766670 Disepalum anomalum: 10.1080/10575639608044938
2709017 Uvaria mocoli: 10.1016/S0031-9422(98)80009-5
235752 Miliusa horsfieldii: 10.1055/S-2002-33804
235744 Meiogyne virgata: 10.1016/S0031-9422(00)81449-1
1129707 Sapranthus palanga: 10.1016/S0031-9422(00)81171-1
2054587 Unonopsis guatterioides: 10.1002/(SICI)1099-1573(199903)13:2<175::AID-PTR395>3.0.CO;2-N
235751 Miliusa cuneata:
235758 Miliusa velutina: 10.1016/S0305-1978(99)00083-6
306934 Oxandra xylopioides:
328402 Zanthoxylum simulans: 10.1021/NP50111A003
1267437 Meiogyne monosperma: 10.1021/NP50062A009
174980 Uvaria rufa: 10.1007/S10600-011-9970-9
306973 Monodora tenuifolia: 10.1055/S-2007-969768
177463 Eulimella: 10.1055/S-2006-962040
295174 Guatteria megalophylla: 10.1021/NP50022A021
2895535 Limaciopsis loangensis: 10.1055/S-0028-1097180
295183 Guatteria punctata: 10.1021/NP50048A018
128258 Magnolia elegans: 10.1016/0031-9422(92)83308-L
86754 Magnolia baillonii: 10.1021/NP50053A020
49857 Annona montana: 10.1016/0031-9422(93)85547-5
235830 Pseuduvaria rugosa: 10.1248/CPB.59.896
527508 Stephania venosa: 10.1021/NP50040A028
461624 Rhigiocarya racemifera: 10.1021/NP50007A010
235797 Huberantha cerasoides: 10.1007/S11418-007-0138-7
295178 Guatteria oliviformis:
295164 Guatteria guianensis: 10.1021/NP0200717
295175 Guatteria multivenia: 10.1021/NP0200717
402570 Guatteria hispida: 10.1021/NP100013R
1129538 Annona papilionella: 10.1021/NP50027A027
681406 Annona acuminata: 10.1021/NP50019A011
235846 Trivalvaria macrophylla: 10.1021/NP50070A013
343279 Guatteria modesta: 10.1021/NP50032A036
86772 Magnolia lanuginosa:
1310094 Monoon cupulare: 10.1080/14786411003774338
261083 Goniothalamus scortechinii: 10.3109/13880208909053943
261087 Goniothalamus tapis: 10.3109/13880208909053943
172644 Broussonetia papyrifera: 10.1007/S10600-007-0042-0
327930 Thalictrum javanicum: 10.1016/0031-9422(88)80247-4
79563 Chydenanthus excelsus: 10.1016/0031-9422(73)85146-5
86759 Magnolia doltsopa: 10.1016/0031-9422(73)85146-5
86726 Magnolia cathcartii: 10.1016/0031-9422(73)85146-5
2029787 Annona emarginata: 10.1055/S-1999-13961
673196 Uvaria versicolor: 10.1002/PTR.1158
343270 Guatteria amplifolia: 10.1016/J.BSE.2011.03.001
306925 Oxandra asbeckii: 10.1021/NP50084A001
74957 Siparuna guianensis: 10.1016/0031-9422(76)85135-7
86757 Magnolia champaca:
111569 Magnolia mexicana:
85854 Magnolia coco:
1267443 Trivalvaria costata: 10.1002/HLCA.200790080
2072264 Mollinedia gilgiana: 10.1002/PCA.584
765229 Mollinedia schottiana: 10.1002/PCA.584
128655 Neolitsea sericea: 10.1248/YAKUSHI1947.86.2_129
344079 Litsea sericea: 10.1248/YAKUSHI1947.86.2_129
85861 Magnolia liliifera: 10.1021/NP50072A043
1631845 Annona macroprophyllata: 10.1080/14786419.2010.533373
74959 Siparuna thecaphora: 10.1016/0031-9422(86)80080-2
497606 Goniothalamus cheliensis: 10.1016/J.CCLET.2008.01.007
672953 Uvaria argentea: 10.1002/PTR.1318

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Shasank S Swain, Sanghamitra Pati, Tahziba Hussain. Quinoline heterocyclic containing plant and marine candidates against drug-resistant Mycobacterium tuberculosis: A systematic drug-ability investigation. European journal of medicinal chemistry. 2022 Mar; 232(?):114173. doi: 10.1016/j.ejmech.2022.114173. [PMID: 35168150]
Quentin R R Coquerel, Fabien Démares, Werner J Geldenhuys, Anne-Marie Le Ray, Dimitri Bréard, Pascal Richomme, Christian Legros, Edmund Norris, Jeffrey R Bloomquist. Toxicity and mode of action of the aporphine plant alkaloid liriodenine on the insect GABA receptor. Toxicon : official journal of the International Society on Toxinology. 2021 Oct; 201(?):141-147. doi: 10.1016/j.toxicon.2021.08.019. [PMID: 34474068]
Emmanoel V Costa, Liviane do N Soares, Jamal da Silva Chaar, Valdenizia R Silva, Luciano de S Santos, Hector H F Koolen, Felipe M A da Silva, Josean F Tavares, Gokhan Zengin, Milena B P Soares, Daniel P Bezerra. Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities. Molecules (Basel, Switzerland). 2021 Jun; 26(12):. doi: 10.3390/molecules26123714. [PMID: 34207059]
InWha Park, Hee Sun Byun, Gang Min Hur, MinKyun Na. Tulipiferamide A, an Alkamide from Liriodendron tulipifera, Exhibits an Anti-Inflammatory Effect via Targeting IKKβ Phosphorylation. Journal of natural products. 2021 05; 84(5):1598-1606. doi: 10.1021/acs.jnatprod.1c00146. [PMID: 33939429]
Yuan-Kun Zheng, Bao-Jun Su, Ya-Qi Wang, Heng-Shan Wang, Hai-Bing Liao, Dong Liang. New Tyramine- and Aporphine-Type Alkamides with NO Release Inhibitory Activities from Piper puberulum. Journal of natural products. 2021 04; 84(4):1316-1325. doi: 10.1021/acs.jnatprod.1c00055. [PMID: 33822610]
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