Santamarin (BioDeep_00000000831)

 

Secondary id: BioDeep_00000868851

human metabolite PANOMIX_OTCML-2023


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 (248.1412)
中文名称: 裂叶苣荚莱内酯
谱图信息: 最多检出来源 Anoectochilus roxburghii(viridiplantae) 75%

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

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

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

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。

亚细胞结构定位 关联基因列表
Cytoplasm 12 ADIG, AIMP2, BCL2, CASP3, CFTR, CHUK, G6PD, MAPK8, PRKAA2, PTGS2, SRARP, STAT3
Peripheral membrane protein 4 G6PD, GORASP1, LPL, PTGS2
Endosome membrane 1 CFTR
Endoplasmic reticulum membrane 4 BCL2, CFTR, HMOX1, PTGS2
Nucleus 14 ADIG, AIMP2, BCL2, CASP3, CFTR, CHUK, GABPA, HMOX1, JUND, MAPK8, PARP1, PRKAA2, SRARP, STAT3
cytosol 11 AIMP2, BCL2, CASP3, CFTR, CHUK, G6PD, HMOX1, MAPK8, PARP1, PRKAA2, STAT3
dendrite 1 PRKAA2
nuclear body 1 PARP1
nucleoplasm 9 CASP3, CHUK, GABPA, HMOX1, JUND, MAPK8, PARP1, PRKAA2, STAT3
RNA polymerase II transcription regulator complex 2 JUND, STAT3
Cell membrane 3 CFTR, LPL, TNF
Cytoplasmic side 2 GORASP1, HMOX1
Early endosome membrane 1 CFTR
Multi-pass membrane protein 1 CFTR
Golgi apparatus membrane 1 GORASP1
Synapse 1 MAPK8
cell surface 3 CFTR, LPL, TNF
glutamatergic synapse 1 CASP3
Golgi apparatus 2 GORASP1, PRKAA2
Golgi membrane 1 GORASP1
lysosomal membrane 1 CFTR
neuronal cell body 3 CASP3, PRKAA2, TNF
Cytoplasm, cytosol 3 AIMP2, G6PD, PARP1
plasma membrane 4 CFTR, LPL, STAT3, TNF
Membrane 8 ADIG, AIMP2, BCL2, CFTR, G6PD, HMOX1, PARP1, PRKAA2
apical plasma membrane 1 CFTR
axon 2 MAPK8, PRKAA2
caveola 1 PTGS2
extracellular exosome 1 G6PD
endoplasmic reticulum 3 BCL2, HMOX1, PTGS2
extracellular space 3 HMOX1, LPL, TNF
perinuclear region of cytoplasm 1 HMOX1
mitochondrion 2 BCL2, PARP1
protein-containing complex 4 BCL2, CFTR, PARP1, PTGS2
intracellular membrane-bounded organelle 1 G6PD
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Secreted 2 ADIG, LPL
extracellular region 3 ADIG, LPL, TNF
cytoplasmic side of plasma membrane 2 CHUK, G6PD
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 ADIG, BCL2
mitochondrial outer membrane 2 BCL2, HMOX1
Extracellular side 1 LPL
transcription regulator complex 3 JUND, PARP1, STAT3
centriolar satellite 1 G6PD
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
CD40 receptor complex 1 CHUK
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 LPL
chylomicron 1 LPL
very-low-density lipoprotein particle 1 LPL
nucleolus 1 PARP1
Early endosome 1 CFTR
recycling endosome 2 CFTR, TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 CFTR
Membrane raft 1 TNF
pore complex 1 BCL2
cis-Golgi network 1 GORASP1
nuclear speck 1 PRKAA2
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
chromatin 4 GABPA, JUND, PARP1, STAT3
phagocytic cup 1 TNF
Chromosome 1 PARP1
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
site of double-strand break 1 PARP1
nuclear envelope 1 PARP1
Recycling endosome membrane 1 CFTR
Lipid droplet 1 ADIG
chloride channel complex 1 CFTR
Golgi-associated vesicle membrane 1 CFTR
cytoplasmic stress granule 1 PRKAA2
myelin sheath 1 BCL2
endoplasmic reticulum lumen 1 PTGS2
transcription repressor complex 1 JUND
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
IkappaB kinase complex 1 CHUK
clathrin-coated endocytic vesicle membrane 1 CFTR
protein-DNA complex 1 PARP1
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
nucleotide-activated protein kinase complex 1 PRKAA2
site of DNA damage 1 PARP1
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalytic complex 1 LPL
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]