Lycopsamine (BioDeep_00000014892)

human metabolite PANOMIX_OTCML-2023

代谢物信息卡片

[(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate

化学式: C15H25NO5 (299.173264)
中文名称: 石松胺, 石松胺
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 3.77%

分子结构信息

SMILES: CC(C)C(C(C)O)(C(=O)OCC1=CCN2C1C(CC2)O)O
InChI: InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12+,13+,15-/m0/s1

描述信息

Lycopsamine, also known as indicine or 9-viridiflorylretronecine, belongs to alkaloids and derivatives class of compounds. Those are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic propertiesand is also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Lycopsamine is soluble (in water) and a very weakly acidic compound (based on its pKa). Lycopsamine can be found in borage, which makes lycopsamine a potential biomarker for the consumption of this food product.
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2270

同义名列表

10 个代谢物同义名

[(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate; indicine, (1S-(1alpha,7(2R*,3S*),7aalpha))-isomer; indicine, (1S-(1alpha,7(2R*,3R*),7aalpha))-isomer; indicine, (1R-(1alpha,7(2S*,3S*),7abeta))-isomer; indicine, (1R-(1alpha,7(2S*,3R*),7abeta))-isomer; 9-Viridiflorylretronecine; lycopsamine; echinatine; Rinderine; indicine

数据库引用编号

33 个数据库交叉引用编号

ChEBI: CHEBI:6598
KEGG: C10347
PubChem: 107938
HMDB: HMDB0301846
Metlin: METLIN68264
KNApSAcK: C00002099
foodb: FDB001505
chemspider: 97061
CAS: 10285-07-1
MoNA: NA003483
MoNA: NA002737
MoNA: NA002340
MoNA: NA003117
MoNA: NA002341
MoNA: NA002735
MoNA: NA002343
MoNA: NA003115
MoNA: NA003482
MoNA: NA002738
MoNA: NA002339
MoNA: NA003480
MoNA: NA003118
MoNA: NA002736
MoNA: NA002342
MoNA: NA003479
MoNA: NA003114
MoNA: NA003481
MoNA: NA003116
MoNA: NA002734
PubChem: 12533
3DMET: B03762
NIKKAJI: J15.603E
RefMet: Lycopsamine

分类词条

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)

77 个相关的物种来源信息

344074 Liatris punctata: 10.1016/0031-9422(92)83487-J
13037 Danaus plexippus: 10.1007/BF01951680
76228 Danaus genutia: 10.1007/BF01951680
192327 Symphytum:
1245804 Lappula spinocarpos: 10.1016/S0305-1978(98)00028-3
170551 Gastrocotyle hispida: 10.1016/S0305-1978(98)00028-3
379304 Trichodesma africanum: 10.1016/S0305-1978(98)00028-3
1213287 Amsinckia menziesii:
2005081 Amsinckia retrorsa: 10.1016/0031-9422(92)83282-4
2005078 Amsinckia grandiflora: 10.1016/0031-9422(92)83282-4
255584 Amsinckia vernicosa: 10.1016/0031-9422(92)83282-4
255598 Amsinckia spectabilis: 10.1016/0031-9422(92)83282-4
102772 Eupatorium chinense: 10.1142/S0192415X92000291
103751 Eupatorium japonicum: 10.1142/S0192415X92000291
102770 Eupatorium cannabinum: 10.1142/S0192415X92000291
203732 Oreocarya virgata: 10.1016/0031-9422(93)85524-U
1213331 Oreocarya thyrsiflora: 10.1016/0031-9422(93)85524-U
1213308 Oreocarya flava: 10.1016/0031-9422(93)85524-U
1452885 Oreocarya cana: 10.1016/0031-9422(93)85524-U
1616932 Cryptantha virginensis: 10.1016/0031-9422(93)85524-U
161689 Echium humile: 10.1016/0031-9422(95)00847-0
248297 Heliotropium indicum: 10.1039/J39670000329
278672 Symphytum officinale:
55598 Ageratum houstonianum: 10.1016/S0031-9422(01)00192-3
764736 Symphytum asperum: 10.1007/978-3-642-49340-9_20
113436 Echium horridum: 10.1515/ZNC-1999-5-601
256501 Pulmonaria obscura: 10.1055/S-2002-32088
454102 Heliotropium megalanthum:
13363 Borago officinalis: 10.1021/NP50034A045
650305 Lithospermum canescens: 10.1515/ZNC-2003-3-405
1212527 Mertensia oblongifolia: 10.1021/NP50060A045
1463737 Mertensia bakeri: 10.1021/NP50060A045
1288209 Mertensia ciliata: 10.1021/NP50060A045
475917 Neatostema apulum: 10.1016/0031-9422(92)83737-J
203740 Lappula squarrosa: 10.3797/SCIPHARM.AUT-05-12
1330311 Lappula myosotis: 10.3797/SCIPHARM.AUT-05-12
102755 Brickellia grandiflora: 10.1016/S0305-1978(02)00049-2
68299 Ageratum conyzoides: 10.1055/S-2006-960211
344074 Liatris punctata: 10.1016/0031-9422(92)83487-J
13037 Danaus plexippus: 10.1007/BF01951680
76228 Danaus genutia: 10.1007/BF01951680
192327 Symphytum:
1245804 Lappula spinocarpos: 10.1016/S0305-1978(98)00028-3
170551 Gastrocotyle hispida: 10.1016/S0305-1978(98)00028-3
379304 Trichodesma africanum: 10.1016/S0305-1978(98)00028-3
1213287 Amsinckia menziesii:
2005081 Amsinckia retrorsa: 10.1016/0031-9422(92)83282-4
2005078 Amsinckia grandiflora: 10.1016/0031-9422(92)83282-4
255584 Amsinckia vernicosa: 10.1016/0031-9422(92)83282-4
255598 Amsinckia spectabilis: 10.1016/0031-9422(92)83282-4
102772 Eupatorium chinense: 10.1142/S0192415X92000291
103751 Eupatorium japonicum: 10.1142/S0192415X92000291
102770 Eupatorium cannabinum: 10.1142/S0192415X92000291
203732 Oreocarya virgata: 10.1016/0031-9422(93)85524-U
1213331 Oreocarya thyrsiflora: 10.1016/0031-9422(93)85524-U
1213308 Oreocarya flava: 10.1016/0031-9422(93)85524-U
1452885 Oreocarya cana: 10.1016/0031-9422(93)85524-U
1616932 Cryptantha virginensis: 10.1016/0031-9422(93)85524-U
161689 Echium humile: 10.1016/0031-9422(95)00847-0
248297 Heliotropium indicum: 10.1039/J39670000329
278672 Symphytum officinale:
55598 Ageratum houstonianum: 10.1016/S0031-9422(01)00192-3
764736 Symphytum asperum: 10.1007/978-3-642-49340-9_20
113436 Echium horridum: 10.1515/ZNC-1999-5-601
256501 Pulmonaria obscura: 10.1055/S-2002-32088
454102 Heliotropium megalanthum:
13363 Borago officinalis: 10.1021/NP50034A045
650305 Lithospermum canescens: 10.1515/ZNC-2003-3-405
1212527 Mertensia oblongifolia: 10.1021/NP50060A045
1463737 Mertensia bakeri: 10.1021/NP50060A045
1288209 Mertensia ciliata: 10.1021/NP50060A045
475917 Neatostema apulum: 10.1016/0031-9422(92)83737-J
203740 Lappula squarrosa: 10.3797/SCIPHARM.AUT-05-12
1330311 Lappula myosotis: 10.3797/SCIPHARM.AUT-05-12
102755 Brickellia grandiflora: 10.1016/S0305-1978(02)00049-2
68299 Ageratum conyzoides: 10.1055/S-2006-960211
9606 Homo sapiens: -

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

Kenny Kuchta, Mathias Schmidt. Safety of medicinal comfrey cream preparations (Symphytum officinale s.l.): The pyrrolizidine alkaloid lycopsamine is poorly absorbed through human skin. Regulatory toxicology and pharmacology : RTP. 2020 Dec; 118(?):104784. doi: 10.1016/j.yrtph.2020.104784. [PMID: 32941922]
Jing Jin, Hao Li, Gaonian Zhao, Su Jiang. Lycopsamine Exerts Protective Effects and Improves Functional Outcome After Spinal Cord Injury in Rats by Suppressing Cell Death. Medical science monitor : international medical journal of experimental and clinical research. 2018 Oct; 24(?):7444-7450. doi: 10.12659/msm.912978. [PMID: 30335732]
Nikoletta Jedlinszki, Boglárka Balázs, Erzsébet Csányi, Dezső Csupor. Penetration of lycopsamine from a comfrey ointment through human epidermis. Regulatory toxicology and pharmacology : RTP. 2017 Feb; 83(?):1-4. doi: 10.1016/j.yrtph.2016.11.015. [PMID: 27840092]
Ammon W Brown, Bryan L Stegelmeier, Steven M Colegate, Dale R Gardner, Kip E Panter, Edward L Knoppel, Jeffery O Hall. The comparative toxicity of a reduced, crude comfrey (Symphytum officinale) alkaloid extract and the pure, comfrey-derived pyrrolizidine alkaloids, lycopsamine and intermedine in chicks (Gallus gallus domesticus). Journal of applied toxicology : JAT. 2016 May; 36(5):716-25. doi: 10.1002/jat.3205. [PMID: 26177929]
Shuai Ji, Ziwei Li, Wei Song, Yongrui Wang, Wenfei Liang, Kai Li, Shunan Tang, Qi Wang, Xue Qiao, Demin Zhou, Siwang Yu, Min Ye. Bioactive Constituents of Glycyrrhiza uralensis (Licorice): Discovery of the Effective Components of a Traditional Herbal Medicine. Journal of natural products. 2016 Feb; 79(2):281-92. doi: 10.1021/acs.jnatprod.5b00877. [PMID: 26841168]
Steven M Colegate, Michael Boppré, Julio Monzón, Joseph M Betz. Pro-toxic dehydropyrrolizidine alkaloids in the traditional Andean herbal medicine "asmachilca". Journal of ethnopharmacology. 2015 Aug; 172(?):179-94. doi: 10.1016/j.jep.2015.06.012. [PMID: 26087231]
Michael Boppré, Steven M Colegate. Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae). Phytochemical analysis : PCA. 2015 May; 26(3):215-25. doi: 10.1002/pca.2555. [PMID: 25645745]
Boris M Mandić, Marina D Vlajić, Snežana S Trifunović, Milena R Simić, Ljubodrag V Vujisić, Ivan M VuČković, Miroslav M Novaković, Snežana D Nikolić-Mandić, Vele V Tešević, Vlatka V Vajs, Slobodan M Milosavljević. Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge. Natural product research. 2015; 29(9):887-90. doi: 10.1080/14786419.2014.991929. [PMID: 25528897]
Elizabeth M Mudge, A Maxwell P Jones, Paula N Brown. Quantification of pyrrolizidine alkaloids in North American plants and honey by LC-MS: single laboratory validation. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2015; 32(12):2068-74. doi: 10.1080/19440049.2015.1099743. [PMID: 26482059]
Damjan Janeš, Samo Kreft. TLC densitometric method for screening of lycopsamine in comfrey root (Symphytum officinale L.) extracts using retrorsine as a reference compound. Acta pharmaceutica (Zagreb, Croatia). 2014 Dec; 64(4):503-8. doi: 10.2478/acph-2014-0031. [PMID: 25531790]
Steven M Colegate, Dale R Gardner, Joseph M Betz, Kip E Panter. Semi-automated separation of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine: preparation of their N-oxides and NMR comparison with diastereoisomeric rinderine and echinatine. Phytochemical analysis : PCA. 2014 Sep; 25(5):429-38. doi: 10.1002/pca.2511. [PMID: 24816769]
Steven M Colegate, Dale R Gardner, T Zane Davis, Joseph M Betz, Kip E Panter. Dehydropyrrolizidine alkaloids in two Cryptantha species: including two new open chain diesters one of which is amphoteric. Phytochemical analysis : PCA. 2013 May; 24(3):201-12. doi: 10.1002/pca.2400. [PMID: 23070903]
Maria T Williams, Bonnie J Warnock, Joseph M Betz, John J Beck, Dale R Gardner, Stephen T Lee, Russell J Molyneux, Steven M Colegate. Detection of high levels of pyrrolizidine-N-oxides in the endangered plant Cryptantha crassipes (Terlingua Creek cat's-eye) using HPLC-ESI-MS. Phytochemical analysis : PCA. 2011 Nov; 22(6):532-40. doi: 10.1002/pca.1314. [PMID: 21433162]
Rahul S Pawar, Erich Grundel, Eugene Mazzola, Kevin D White, Alexander J Krynitsky, Jeanne I Rader. Chiral stationary phases for separation of intermedine and lycopsamine enantiomers from Symphytum uplandicum. Journal of separation science. 2010 Feb; 33(2):200-5. doi: 10.1002/jssc.200900611. [PMID: 20029846]
Feng Liu, Sow Yin Wan, Zhangjian Jiang, Sam Fong Yau Li, Eng Shi Ong, Jhon Carlos Castaño Osorio. Determination of pyrrolizidine alkaloids in comfrey by liquid chromatography-electrospray ionization mass spectrometry. Talanta. 2009 Dec; 80(2):916-23. doi: 10.1016/j.talanta.2009.08.020. [PMID: 19836573]
Cordula Frölich, Dietrich Ober, Thomas Hartmann. Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species. Phytochemistry. 2007 Apr; 68(7):1026-37. doi: 10.1016/j.phytochem.2007.01.002. [PMID: 17320124]
Xiao-min Yu, Xin-min Liu, Yong-fen Qi, Zhi-gang Zhang, Chao-shu Tang. [The protective effects of intermedin 1-53 on oleic acid induced acute lung injury in rats]. Zhonghua jie he he hu xi za zhi = Zhonghua jiehe he huxi zazhi = Chinese journal of tuberculosis and respiratory diseases. 2006 Dec; 29(12):808-11. doi: NULL. [PMID: 17327082]
I Narberhaus, C Theuring, T Hartmann, S Dobler. Uptake and metabolism of pyrrolizidine alkaloids in Longitarsus flea beetles (Coleoptera: Chrysomelidae) adapted and non-adapted to alkaloid-containing host plants. Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology. 2003 Aug; 173(6):483-91. doi: 10.1007/s00360-003-0356-6. [PMID: 12802610]
W Haberer, L Witte, Th Hartmann, S Dobler. Pyrrolizidine alkaloids in Pulmonaria obscura. Planta medica. 2002 May; 68(5):480-2. doi: 10.1055/s-2002-32088. [PMID: 12058336]
T Hartmann, C Theuring, L Witte, J M Pasteels. Sequestration, metabolism and partial synthesis of tertiary pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi. Insect biochemistry and molecular biology. 2001 Oct; 31(11):1041-56. doi: 10.1016/s0965-1748(01)00052-2. [PMID: 11520683]
M M Ames, J S Miser, W A Smithson, P F Coccia, C S Hughes, D M Davis. Pharmacokinetic study of indicine N-oxide in pediatric cancer patients. Cancer chemotherapy and pharmacology. 1982 Dec; 10(1):43-6. doi: 10.1007/bf00257237. [PMID: 7160044]
M M Ames, G Powis. Determination of indicine N-oxide and indicine in plasma and urine by electron-capture gas-liquid chromatography. Journal of chromatography. 1978 Dec; 166(2):519-26. doi: 10.1016/s0021-9673(00)95636-x. [PMID: 748361]
R REIMANN-HUNZIKER, W WILD. INDICINE--HORMONAL BIRTH CONTROL ON A NATURAL BASIS. Journal of reproduction and fertility. 1963 Aug; 6(?):175-8. doi: 10.1530/jrf.0.0060175. [PMID: 14064208]