Intermedina (BioDeep_00000395504)

PANOMIX_OTCML-2023

代谢物信息卡片

化学式: C15H25NO5 (299.173264)
中文名称: 促黑激素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 3.51%

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+/m1/s1

描述信息

Intermedine is a carboxylic ester compound formed from condensation between retronecine and (2S,3R)-2,3-dihydroxy-2-isopropylbutanoic acid. It is a member of pyrrolizines, an azabicycloalkane and a carboxylic ester.
Intermedine is a natural product found in Eupatorium cannabinum, Chromolaena odorata, and other organisms with data available.
See also: Comfrey Leaf (part of); Comfrey Root (part of).

同义名列表

19 个代谢物同义名

Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3R)-; Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1R-[1?,7(2S*,3R*),7a?]]-; Intermedine (7CI,8CI); (+)-Intermedine; 3-epi-Lycopsamine; BUTANOIC ACID, 2,3-DIHYDROXY-2-(1-METHYLETHYL)-, (2,3,5,7A-TETRAHYDRO-1-HYDROXY-1H-PYRROLIZIN-7-YL)METHYL ESTER, (1R-(1.ALPHA.,7(2S*,3R*),7A.BETA.))-; Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (1R-(1alpha,7(2S*,3R*),7abeta))-; Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, ((1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (2S,3R)-; (2S,3R)-2,3-Dihydroxy-2-(1-methylethyl)butanoic Acid [(1R,7aR)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl Ester; [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate; [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolo[1,2-a]pyrrol-7-yl]methyl (2S,3R)-2,3-dihydroxy-2-isopropylbutanoate; ((1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S,3R)-2,3-dihydroxy-2-isopropylbutanoate; 9-(+)-Trachelanthylretronecine; Intermedine, HPLC Grade; Intermedine, (+)-; 3-EPI-LYCOPSAMINE; UNII-DLC9FEP81A; (+)-Intermedine; Intermedinum; Intermedina; intermedine; DLC9FEP81A; 1ST14165

数据库引用编号

12 个数据库交叉引用编号

ChEBI: CHEBI:5941
KEGG: C10330
PubChem: 114843
MeSH: intermedine
ChemIDplus: 0010285060
KNApSAcK: C00002093
CAS: 10285-06-0
CAS: 1414-01-3
medchemexpress: HY-113845
PubChem: 12516
3DMET: B03747
NIKKAJI: J15.602G

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)

70 个相关的物种来源信息

344074 Liatris punctata: 10.1016/0031-9422(92)83487-J
76228 Danaus genutia: 10.1007/BF01951680
13037 Danaus plexippus: 10.1007/BF01951680
192327 Symphytum:
379304 Trichodesma africanum:
170551 Gastrocotyle hispida: 10.1016/S0305-1978(98)00028-3
1245804 Lappula spinocarpos: 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
103751 Eupatorium japonicum: 10.1142/S0192415X92000291
102772 Eupatorium chinense: 10.1142/S0192415X92000291
102770 Eupatorium cannabinum: 10.1142/S0192415X92000291
1213331 Oreocarya thyrsiflora: 10.1016/0031-9422(93)85524-U
203732 Oreocarya virgata: 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
2006872 Cryptantha clevelandii: 10.1016/0031-9422(93)85524-U
1213317 Cryptantha leiocarpa: 10.1016/0031-9422(93)85524-U
1616932 Cryptantha virginensis: 10.1016/0031-9422(93)85524-U
103745 Chromolaena odorata: 10.1016/S0031-9422(00)90573-9
287011 Praxelis clematidea: 10.1016/S0031-9422(98)00203-9
55598 Ageratum houstonianum: 10.1016/S0031-9422(01)00192-3
278672 Symphytum officinale:
764736 Symphytum asperum: 10.1007/978-3-642-49340-9_20
256501 Pulmonaria obscura: 10.1055/S-2002-32088
764718 Amsinckia calycina: 10.1071/CH9661955
1212517 Amsinckia lycopsoides: 10.1071/CH9661955
1288209 Mertensia ciliata: 10.1021/NP50060A045
203740 Lappula squarrosa: 10.3797/SCIPHARM.AUT-05-12
1330311 Lappula myosotis: 10.3797/SCIPHARM.AUT-05-12
34254 Lithospermum erythrorhizon: 10.1016/0031-9422(90)85153-7
89630 Anchusa officinalis: 10.3891/ACTA.CHEM.SCAND.34B-0075
344074 Liatris punctata: 10.1016/0031-9422(92)83487-J
76228 Danaus genutia: 10.1007/BF01951680
13037 Danaus plexippus: 10.1007/BF01951680
192327 Symphytum:
379304 Trichodesma africanum:
170551 Gastrocotyle hispida: 10.1016/S0305-1978(98)00028-3
1245804 Lappula spinocarpos: 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
103751 Eupatorium japonicum: 10.1142/S0192415X92000291
102772 Eupatorium chinense: 10.1142/S0192415X92000291
102770 Eupatorium cannabinum: 10.1142/S0192415X92000291
1213331 Oreocarya thyrsiflora: 10.1016/0031-9422(93)85524-U
203732 Oreocarya virgata: 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
2006872 Cryptantha clevelandii: 10.1016/0031-9422(93)85524-U
1213317 Cryptantha leiocarpa: 10.1016/0031-9422(93)85524-U
1616932 Cryptantha virginensis: 10.1016/0031-9422(93)85524-U
103745 Chromolaena odorata: 10.1016/S0031-9422(00)90573-9
287011 Praxelis clematidea: 10.1016/S0031-9422(98)00203-9
55598 Ageratum houstonianum: 10.1016/S0031-9422(01)00192-3
278672 Symphytum officinale:
764736 Symphytum asperum: 10.1007/978-3-642-49340-9_20
256501 Pulmonaria obscura: 10.1055/S-2002-32088
764718 Amsinckia calycina: 10.1071/CH9661955
1212517 Amsinckia lycopsoides: 10.1071/CH9661955
1288209 Mertensia ciliata: 10.1021/NP50060A045
203740 Lappula squarrosa: 10.3797/SCIPHARM.AUT-05-12
1330311 Lappula myosotis: 10.3797/SCIPHARM.AUT-05-12
34254 Lithospermum erythrorhizon: 10.1016/0031-9422(90)85153-7
89630 Anchusa officinalis: 10.3891/ACTA.CHEM.SCAND.34B-0075

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

Ziqi Wang, Haolei Han, Chen Wang, Qinqin Zheng, Hongping Chen, Xiangchun Zhang, Ruyan Hou. Hepatotoxicity of Pyrrolizidine Alkaloid Compound Intermedine: Comparison with Other Pyrrolizidine Alkaloids and Its Toxicological Mechanism. Toxins. 2021 11; 13(12):. doi: 10.3390/toxins13120849. [PMID: 34941687]
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]
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]
Daniel J Vis, Johan A Westerhuis, Huub C J Hoefsloot, Ferdinand Roelfsema, Margriet M W B Hendriks, Age K Smilde. Detecting regulatory mechanisms in endocrine time series measurements. PloS one. 2012; 7(3):e32985. doi: 10.1371/journal.pone.0032985. [PMID: 22461889]
Ai-Leng Khoo, Hans J P M Koenen, Louis Y A Chai, Fred C G J Sweep, Mihai G Netea, André J A M van der Ven, Irma Joosten. Seasonal variation in vitamin D₃ levels is paralleled by changes in the peripheral blood human T cell compartment. PloS one. 2012; 7(1):e29250. doi: 10.1371/journal.pone.0029250. [PMID: 22235276]
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]
Nan Mei, Lei Guo, Peter P Fu, James C Fuscoe, Yang Luan, Tao Chen. Metabolism, genotoxicity, and carcinogenicity of comfrey. Journal of toxicology and environmental health. Part B, Critical reviews. 2010 Oct; 13(7-8):509-26. doi: 10.1080/10937404.2010.509013. [PMID: 21170807]
Maria Fernanda Pereira Lavieri Gomes, Cristina de Oliveira Massoco, José Guilherme Xavier, Leoni Villano Bonamin. Comfrey (Symphytum Officinale. l.) and Experimental Hepatic Carcinogenesis: A Short-term Carcinogenesis Model Study. Evidence-based complementary and alternative medicine : eCAM. 2010 Jun; 7(2):197-202. doi: 10.1093/ecam/nem172. [PMID: 18955295]
Vladimir Blagaić, Karlo Houra, Petra Turcić, Nikola Stambuk, Pasko Konjevoda, Alenka Boban-Blagaić, Tomislav Kelava, Marina Kos, Gorana Aralica, Filip Culo. The influence of alpha-, beta-, and gamma-melanocyte stimulating hormone on acetaminophen induced liver lesions in male CBA mice. Molecules (Basel, Switzerland). 2010 Mar; 15(3):1232-41. doi: 10.3390/molecules15031232. [PMID: 20335976]
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]
E Sánchez, V C Rubio, J M Cerdá-Reverter. Characterization of the sea bass melanocortin 5 receptor: a putative role in hepatic lipid metabolism. The Journal of experimental biology. 2009 Dec; 212(Pt 23):3901-10. doi: 10.1242/jeb.035121. [PMID: 19915133]
Jiling Wu, Sheng Li, Hanyu Jiang, Yuhong Gao, Junyi Niu. [Staining and slide-preparing technique of mitotic chromosomes and application in karyotype determination of Ephedra]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Nov; 34(21):2725-9. doi: ". [PMID: 20209901]
Yoshio Okada. [Overview in 45 years of studies on peptide chemistry]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2009 Oct; 129(10):1141-54. doi: 10.1248/yakushi.129.1141. [PMID: 19797870]
Hiroshi Kamisoyama, Kazuhisa Honda, Takaoki Saneyasu, Kunio Sugahara, Shin Hasegawa. Corticotropin-releasing factor is a downstream mediator of the beta-melanocyte-stimulating hormone-induced anorexigenic pathway in chicks. Neuroscience letters. 2009 Jul; 458(3):102-5. doi: 10.1016/j.neulet.2009.04.041. [PMID: 19393716]
Katrina A Bicknell, Stephen C Harmer, Stephanie Yiangson, Wendy Lockwood, Andrew B Bicknell. Lys-gamma3-MSH: a global regulator of hormone sensitive lipase activity?. Molecular and cellular endocrinology. 2009 Mar; 300(1-2):71-6. doi: 10.1016/j.mce.2008.09.032. [PMID: 18977407]
Ferruccio Santini, Margherita Maffei, Caterina Pelosini, Guido Salvetti, Giovanna Scartabelli, Aldo Pinchera. Melanocortin-4 receptor mutations in obesity. Advances in clinical chemistry. 2009; 48(?):95-109. doi: NULL. [PMID: 19803416]
M L Smith, B Prall, W Nandar, M A Cline. Beta-melanocyte-stimulating hormone potently reduces appetite via the hypothalamus in chicks. Journal of neuroendocrinology. 2008 Feb; 20(2):220-6. doi: 10.1111/j.1365-2826.2007.01639.x. [PMID: 18088360]
Nan Mei, Lei Guo, Lu Zhang, Leming Shi, Yongming Andrew Sun, Chris Fung, Carrie L Moland, Stacey L Dial, James C Fuscoe, Tao Chen. Analysis of gene expression changes in relation to toxicity and tumorigenesis in the livers of Big Blue transgenic rats fed comfrey (Symphytum officinale). BMC bioinformatics. 2006 Sep; 7 Suppl 2(?):S16. doi: 10.1186/1471-2105-7-s2-s16. [PMID: 17118137]
J M Wood, N C J Gibbons, K U Schallreuter. Melanocortins in human melanocytes. Cellular and molecular biology (Noisy-le-Grand, France). 2006 May; 52(2):75-8. doi: NULL. [PMID: 16914090]
Sarah A Nickolls, Beth Fleck, Sam R J Hoare, Rich A Maki. Functional selectivity of melanocortin 4 receptor peptide and nonpeptide agonists: evidence for ligand-specific conformational states. The Journal of pharmacology and experimental therapeutics. 2005 Jun; 313(3):1281-8. doi: 10.1124/jpet.105.083337. [PMID: 15743921]
Katrin Fricke, Axel Schulz, Harald John, Wolf-Georg Forssmann, Erik Maronde. Isolation and characterization of a novel proopiomelanocortin-derived peptide from hemofiltrate of chronic renal failure patients. Endocrinology. 2005 Apr; 146(4):2060-8. doi: 10.1210/en.2004-1097. [PMID: 15650078]
N Mei, L Guo, P P Fu, R H Heflich, T Chen. Mutagenicity of comfrey (Symphytum Officinale) in rat liver. British journal of cancer. 2005 Mar; 92(5):873-5. doi: 10.1038/sj.bjc.6602420. [PMID: 15726100]
Janis Klovins, Tatjana Haitina, Davids Fridmanis, Zuzana Kilianova, Ivo Kapa, Robert Fredriksson, Nicole Gallo-Payet, Helgi B Schiöth. The melanocortin system in Fugu: determination of POMC/AGRP/MCR gene repertoire and synteny, as well as pharmacology and anatomical distribution of the MCRs. Molecular biology and evolution. 2004 Mar; 21(3):563-79. doi: 10.1093/molbev/msh050. [PMID: 14694081]
Iu A Pankov. [Protein hormones, receptors, and other proteins in mechanisms of hormonal regulation]. Biomeditsinskaia khimiia. 2004 Mar; 50(2):121-35. doi: ". [PMID: 15179819]
T Hartmann, C Theuring, L Witte, S Schulz, J M Pasteels. Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi. Insect biochemistry and molecular biology. 2003 May; 33(5):515-23. doi: 10.1016/s0965-1748(03)00026-2. [PMID: 12706631]
Jacques M Pasteels, Claudine Theuring, Ludger Witte, Thomas Hartmann. Sequestration and metabolism of protoxic pyrrolizidine alkaloids by larvae of the leaf beetle Platyphora boucardi and their transfer via pupae into defensive secretions of adults. Journal of chemical ecology. 2003 Feb; 29(2):337-55. doi: 10.1023/a:1022629911304. [PMID: 12737262]
Douglas J MacNeil, Andrew D Howard, Xiaoming Guan, Tung M Fong, Ravi P Nargund, Maria A Bednarek, Mark T Goulet, David H Weinberg, Alison M Strack, Donald J Marsh, Howard Y Chen, Chun-Pyn Shen, Airu S Chen, Charles I Rosenblum, Tanya MacNeil, Michael Tota, Euan D MacIntyre, Lex H T Van der Ploeg. The role of melanocortins in body weight regulation: opportunities for the treatment of obesity. European journal of pharmacology. 2002 Aug; 450(1):93-109. doi: 10.1016/s0014-2999(02)01989-1. [PMID: 12176114]
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]
Douglas J MacNeil, Andrew D Howard, Xiaoming Guan, Tung M Fong, Ravi P Nargund, Maria A Bednarek, Mark T Goulet, David H Weinberg, Alison M Strack, Donald J Marsh, Howard Y Chen, Chun-Pyn Shen, Airu S Chen, Charles I Rosenblum, Tanya MacNeil, Michael Tota, Euan D MacIntyre, Lex H T Van der Ploeg. The role of melanocortins in body weight regulation: opportunities for the treatment of obesity. European journal of pharmacology. 2002 Apr; 440(2-3):141-57. doi: 10.1016/s0014-2999(02)01425-5. [PMID: 12007532]
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]
A F Nikkels, G E Piérard. Medical mystery: the answer. The New England journal of medicine. 2001 May; 344(21):1642-3. doi: 10.1056/nejm200105243442115. [PMID: 11372019]