Santamarin (BioDeep_00000000831)

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds

代谢物信息卡片

NAPHTHO(1,2-B)FURAN-2(3H)-ONE, 3A,4,5,5A,6,7,9A,9B-OCTAHYDRO-6-HYDROXY-5A,9-DIMETHYL-3-METHYLENE-, (3AS-(3A.ALPHA.,5A.BETA.,6.BETA.,9A.ALPHA.,9B.BETA.))-

化学式: C15H20O3 (248.14123700000002)
中文名称: 裂叶苣荚莱内酯
谱图信息: 最多检出来源 Anoectochilus roxburghii(viridiplantae) 60%

分子结构信息

SMILES: C=C1C(=O)OC2C1CCC1(C)C(O)CC=C(C)C21
InChI: InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1

描述信息

Santamarin, also known as (+)-santamarine or balchanin, belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Santamarin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Santamarin can be found in sweet bay, which makes santamarin a potential biomarker for the consumption of this food product.
Santamarin is a sesquiterpene lactone of the eudesmanolide group.
Santamarine is a natural product found in Centaurea uniflora, Eupatorium capillifolium, and other organisms with data available.

同义名列表

23 个代谢物同义名

NAPHTHO(1,2-B)FURAN-2(3H)-ONE, 3A,4,5,5A,6,7,9A,9B-OCTAHYDRO-6-HYDROXY-5A,9-DIMETHYL-3-METHYLENE-, (3AS-(3A.ALPHA.,5A.BETA.,6.BETA.,9A.ALPHA.,9B.BETA.))-; Naphtho(1,2-b)furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS-(3aalpha,5abeta,6beta,9aalpha,9bbeta))-; (3aS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-Decahydro-6alpha-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one; Naphtho(1,2-b)furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,6R,9aS,9bS)-; (3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6a-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one; (3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6α-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one; (3AS,5AR,6R,9AS,9BS)-6-HYDROXY-5A,9-DIMETHYL-3-METHYLIDENE-2H,3H,3AH,4H,5H,5AH,6H,7H,9AH,9BH-NAPHTHO[1,2-B]FURAN-2-ONE; (3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-b]furan-2(3H)-one; (3aS,5aR,6R,9aS,9bS)-6-Hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydro-3H-naphtho[1,2-b]furan-2-one; (3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one; (3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g]benzofuran-2-one; Naphthol]1,2-b]furan-2(3H)-one,3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene; Eudesma-3,11(13)-dien-12-oic acid, 1.beta.,6.alpha.-dihydroxy-, .gamma.-lactone; Eudesma-3,11(13)-dien-12-oic acid, 1beta,6alpha-dihydroxy-, gamma-lactone; Santamarin;Balchanin; SCHEMBL22305508; (+)-santamarine; UNII-15D6KW291H; Santamarine; santamarin; 15D6KW291H; Balchanin; Santamarin

数据库引用编号

21 个数据库交叉引用编号

ChEBI: CHEBI:9023
KEGG: C09544
PubChem: 188297
PubChem: 331391
HMDB: HMDB0302709
Metlin: METLIN67792
ChEMBL: CHEMBL89311
MeSH: santamarine
ChemIDplus: 0004290135
KNApSAcK: C00003363
foodb: FDB005897
chemspider: 163664
CAS: 4290-13-5
medchemexpress: HY-N1326
PMhub: MS000004990
PubChem: 11735
3DMET: B03066
NIKKAJI: J14.435E
KNApSAcK: 9023
LOTUS: LTS0266184
wikidata: Q27089375

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)

48 个相关的物种来源信息

282722 - Achillea biebersteinii:
282747 - Achillea micrantha:
13329 - Achillea millefolium:
282759 - Achillea pratensis:
2067512 - Ambrosia confertiflora: 10.1016/S0031-9422(00)85188-2
589761 - Anthemis macedonica: 10.1016/J.PHYTOCHEM.2007.07.021
133268 - Argyranthemum adauctum: 10.1016/S0031-9422(00)82618-7
1903191 - Artemisia balchanorum: 10.1016/S0040-4039(00)90788-3
223866 - Artemisia genipi: 10.1016/S0040-4039(00)90788-3
72329 - Artemisia herba-alba: 10.1016/S0031-9422(00)89536-9
72329 - Artemisia herba-alba: 10.1016/S0031-9422(00)97936-6
72345 - Artemisia lucentica: 10.1016/S0031-9422(00)89536-9
72345 - Artemisia lucentica: 10.1016/S0031-9422(00)97936-6
86312 - Artemisia ludoviciana:
72350 - Artemisia reptans: 10.1016/S0031-9422(00)89536-9
72350 - Artemisia reptans: 10.1016/S0031-9422(00)97936-6
205374 - Artemisia rutifolia: 10.1016/0031-9422(92)83319-T
72353 - Artemisia splendens: 10.1021/NP800468M
72355 - Artemisia umbelliformis: 10.1021/NP800468M
72356 - Artemisia verlotiorum: 10.1016/S0031-9422(00)95017-9
401941 - Artemisia xanthochroa: 10.1016/0031-9422(86)80021-8
4210 - Asteraceae: 10.1016/J.INTIMP.2012.04.016
1898889 - Callostylis rigida: 10.1016/0031-9422(89)80289-4
145508 - Centaurea ornata: 10.1021/NP50069A006
1000417 - Centaurea uniflora: 10.1016/0031-9422(86)80082-6
179395 - Chamaemelum fuscatum: 10.1016/S0031-9422(00)81291-1
1204776 - Cyathocline purpurea:
1204776 - Cyathocline purpurea: 10.1016/0031-9422(81)84063-0
434655 - Eremanthus erythropappus: 10.1021/NP50042A020
102771 - Eupatorium capillifolium: 10.1007/S11418-006-0007-9
102771 - Eupatorium capillifolium: 10.1055/S-2006-962665
413573 - Guizotia scabra: 10.1016/0031-9422(91)84212-B
9606 - Homo sapiens: -
127985 - Inulanthera calva: 10.1016/S0031-9422(00)95195-1
1721052 - Inulanthera dregeana: 10.1016/S0031-9422(00)95195-1
883014 - Lactuca floridana: 10.1016/0031-9422(95)00478-P
85223 - Laurus nobilis:
55740 - Liabum solidagineum: 10.1016/S0031-9422(00)83499-8
3406 - Magnolia grandiflora: 10.1016/J.PHYTOCHEM.2018.08.006
111567 - Magnolia kachirachirai: 10.1002/HLCA.201000289
121888 - Podachaenium eminens: 10.1055/S-2000-8649
52307 - Rudbeckia subtomentosa: 10.1016/0031-9422(90)85117-X
324593 - Saussurea costus:
324593 - Saussurea costus: 10.3390/MOLECULES14010266
1053329 - Symphyotrichum subulatum var. squamatum: 10.21608/BFSA.1984.89869
99105 - Tanacetum: 10.1016/J.JEP.2017.02.023
314068 - Tanacetum argenteum: 10.1016/S0031-9422(96)00790-X
127999 - Tanacetum parthenium:

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

Jung Im Lee, Jung Hwan Oh, Fatih Karadeniz, Chang-Suk Kong, Youngwan Seo. Inhibitory Effects of Sesquiterpenoids Isolated from Artemisia scoparia on Adipogenic Differentiation of 3T3-L1 Preadipocytes. International journal of molecular sciences. 2023 Dec; 25(1):. doi: 10.3390/ijms25010200. [PMID: 38203371]
Lara Dürr, Jakob K Reinhardt, Maciej Dobrzyński, Tanja Hell, Martin Smieško, Olivier Pertz, Matthias Hamburger, Eliane Garo. A Dimerosesquiterpene and Sesquiterpene Lactones from Artemisia argyi Inhibiting Oncogenic PI3K/AKT Signaling in Melanoma Cells. Journal of natural products. 2022 11; 85(11):2557-2569. doi: 10.1021/acs.jnatprod.2c00471. [PMID: 36351173]
Jin-Ping Wang, Tian-Ze Li, Xiao-Yan Huang, Chang-An Geng, Cheng Shen, Jin-Jin Sun, Dong Xue, Ji-Jun Chen. Synthesis and anti-fibrotic effects of santamarin derivatives as cytotoxic agents against hepatic stellate cell line LX2. Bioorganic & medicinal chemistry letters. 2021 06; 41(?):127994. doi: 10.1016/j.bmcl.2021.127994. [PMID: 33775837]
Sajid Jalal, Bashir Ahmad, Ting Zhang, Lianying Guo, Lin Huang. SANTAMARINE: Mechanistic studies on multiple diseases. Chemical biology & drug design. 2020 04; 95(4):427-434. doi: 10.1111/cbdd.13666. [PMID: 32022458]
Jakob K Reinhardt, Amy M Klemd, Ombeline Danton, Maria De Mieri, Martin Smieško, Roman Huber, Thomas Bürgi, Carsten Gründemann, Matthias Hamburger. Sesquiterpene Lactones from Artemisia argyi: Absolute Configuration and Immunosuppressant Activity. Journal of natural products. 2019 06; 82(6):1424-1433. doi: 10.1021/acs.jnatprod.8b00791. [PMID: 31181920]
Hu Wei, Chunnian He, Yong Peng, Guoxu Ma, Peigen Xiao. [Chemical constituents of Dolomiaea souliei]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 May; 37(9):1249-53. doi: . [PMID: 22803370]
Ting Zhang, Lin Ma, Feng Wu, Ruoyun Chen. [Chemical constituents from a portion of ethanolicextract of Saussurea lappa roots]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 May; 37(9):1232-6. doi: . [PMID: 22803366]
Xiao-ping Zhao, Lin Lu, Bin Hu, Shu-fang Wang. [Screening and identifying hepatotoxic components in Aucklandiae Radix with GC-MS]. Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences. 2012 01; 41(1):43-6. doi: 10.3785/j.issn.1008-9292.2012.01.007. [PMID: 22419462]
Anil Pareek, Manish Suthar, Garvendra S Rathore, Vijay Bansal. Feverfew (Tanacetum parthenium L.): A systematic review. Pharmacognosy reviews. 2011 Jan; 5(9):103-10. doi: 10.4103/0973-7847.79105. [PMID: 22096324]
Jin-Ao Duan, Pengfei Hou, Yuping Tang, Pei Liu, Shulan Su, Hanqing Liu. A new sesquiterpene and other constituents from Saussurea lappa root. Natural product communications. 2010 Oct; 5(10):1531-4. doi: . [PMID: 21121241]
Guoyi Ma, Li Chong, Zuqiang Li, Andrew H T Cheung, Martin H N Tattersall. Anticancer activities of sesquiterpene lactones from Cyathocline purpurea in vitro. Cancer chemotherapy and pharmacology. 2009 Jun; 64(1):143-52. doi: 10.1007/s00280-008-0863-y. [PMID: 18998133]
Simona De Marino, Nicola Borbone, Franco Zollo, Angela Ianaro, Paola Di Meglio, Maria Iorizzi. New sesquiterpene lactones from Laurus nobilis leaves as inhibitors of nitric oxide production. Planta medica. 2005 Aug; 71(8):706-10. doi: 10.1055/s-2005-864191. [PMID: 16142632]
Chang-Ming Sun, Wan-Jr Syu, Ming-Jaw Don, Jang-Jih Lu, Gum-Hee Lee. Cytotoxic sesquiterpene lactones from the root of Saussurea lappa. Journal of natural products. 2003 Sep; 66(9):1175-80. doi: 10.1021/np030147e. [PMID: 14510592]
C L Cantrell, S G Franzblau, N H Fischer. Antimycobacterial plant terpenoids. Planta medica. 2001 Nov; 67(8):685-94. doi: 10.1055/s-2001-18365. [PMID: 11731906]
H Matsuda, H Shimoda, T Uemura, M Yoshikawa. Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying. Bioorganic & medicinal chemistry letters. 1999 Sep; 9(18):2647-52. doi: 10.1016/s0960-894x(99)00442-4. [PMID: 10509909]
J Y Cho, J Park, E S Yoo, K U Baik, J H Jung, J Lee, M H Park. Inhibitory effect of sesquiterpene lactones from Saussurea lappa on tumor necrosis factor-alpha production in murine macrophage-like cells. Planta medica. 1998 Oct; 64(7):594-7. doi: 10.1055/s-2006-957528. [PMID: 9810262]
R J Marles, J Kaminski, J T Arnason, L Pazos-Sanou, S Heptinstall, N H Fischer, C W Crompton, D G Kindack, D V Awang. A bioassay for inhibition of serotonin release from bovine platelets. Journal of natural products. 1992 Aug; 55(8):1044-56. doi: 10.1021/np50086a003. [PMID: 1431933]
I O Mondranondra, C T Che, A M Rimando, S Vajrodaya, H H Fong, N R Farnsworth. Sesquiterpene lactones and other constituents from a cytotoxic extract of Michelia floribunda. Pharmaceutical research. 1990 Dec; 7(12):1269-72. doi: 10.1023/a:1015937921880. [PMID: 2095565]
F S el-Feraly, Y M Chan. Isolation and characterization of the sesquiterpene lactones costunolide, parthenolide, costunolide diepoxide, santamarine, and reynosin from Magnolia grandiflora L. Journal of pharmaceutical sciences. 1978 Mar; 67(3):347-50. doi: 10.1002/jps.2600670319. [PMID: 641720]