Cinnamtannin A2 (BioDeep_00000001071)

   

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

化学式: C60H50O24 (1154.2692)
中文名称: 肉桂鞣质A2
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=C3C(=CC(=C4C5C(C(OC6=C(C(=CC(=C56)O)O)C7C(C(OC8=CC(=CC(=C78)O)O)C9=CC(=C(C=C9)O)O)O)C1=CC(=C(C=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O
InChI: InChI=1S/C60H50O24/c61-23-13-34(71)42-41(14-23)81-55(20-2-6-26(63)31(68)10-20)51(78)48(42)44-36(73)17-38(75)46-50(53(80)57(83-59(44)46)22-4-8-28(65)33(70)12-22)47-39(76)18-37(74)45-49(52(79)56(84-60(45)47)21-3-7-27(64)32(69)11-21)43-35(72)16-29(66)24-15-40(77)54(82-58(24)43)19-1-5-25(62)30(67)9-19/h1-14,16-18,40,48-57,61-80H,15H2/t40-,48-,49+,50-,51-,52-,53-,54-,55-,56-,57-/m1/s1

描述信息

Cinnamtannin A2 is a proanthocyanidin isolated from Cinnamomum cassia. It has a role as a plant metabolite.
Cinnamtannin A2 is a natural product found in Cinnamomum iners, Cinnamomum aromaticum, and other organisms with data available.
Isolated from Cinnamomum cassia (Chinese cinnamon). Cinnamtannin A2 is found in many foods, some of which are cocoa bean, chinese cinnamon, chocolate, and herbs and spices.
Cinnamtannin A2 is found in chinese cinnamon. Cinnamtannin A2 is isolated from Cinnamomum cassia (Chinese cinnamon).
A proanthocyanidin isolated from Cinnamomum cassia.

同义名列表

13 个代谢物同义名

(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol; (1(2)R,1(3)R,1(4)R,2(2)R,2(3)R,2(4)R,3(2)R,3(3)R,3(4)S,4(2)R,4(3)R)-1(2),2(2),3(2),4(2)-tetrakis(3,4-dihydroxyphenyl)-1(3),1(4),2(3),2(4),3(3),3(4),4(3),4(4)-octahydro-1(2)H,2(2)H,3(2)H,4(2)2H-[1(4),2(8):2(4),3(8):3(4),4(8)-quater-1-benzopyran]-1(3),1(5),1(7),2(3),2(5),2(7),3(3),3(5),3(7),4(3),4(5),4(7)-dodecol; (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]-3,5,7-trihydroxy-chroman-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol; [4,8:4,8:4,8-Quater-2H-1-benzopyran]-3,3,3,3,5,5,5,5,7,7,7,7-dodecol, 2,2,2,2-tetrakis(3,4-dihydroxyphenyl)-3,3,3,3,4,4,4,4-octahydro-, (2R,2R,2R,2R,3R,3R,3R,3R,4R,4R,4S)-; (2R,2R,2R,2R,3R,3R,3R,3R,4R,4S,4S)-2,2,2,2-Tetrakis(3,4-dihydroxyphenyl)-3,3,3,3,4,4,4,4-octahydro-2H,2H,2H,2H-4,8:4,8:4,8-quaterchromene-3,3,3,3,5,5,5,5,7,7,7,7-dodecol; [Epicatechin(4b->8)]3-epicatechin; Tetrameric proanthocyanidin; Epicatechin tetramer; Procyanidin tetramer; Cinnamtannin A2; Cinnamtannin I; Cinnamtannin A1



数据库引用编号

19 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)

71 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 10 AKR1B1, ALOX5, CA1, CA3, IRS1, KEAP1, NOS3, PIK3CA, PRKAA2, TYR
Peripheral membrane protein 1 ALOX5
Endosome membrane 1 INSR
Nucleus 6 FOS, GABPA, IRS1, KEAP1, NOS3, PRKAA2
cytosol 11 AKR1B1, ALOX5, CA1, CA3, FOS, IRS1, KEAP1, NOS3, PIK3CA, PRKAA2, SLC2A4
dendrite 1 PRKAA2
trans-Golgi network 1 SLC2A4
nucleoplasm 8 AKR1B1, ALOX5, FOS, GABPA, IRS1, KEAP1, NOS3, PRKAA2
RNA polymerase II transcription regulator complex 1 FOS
Cell membrane 3 HAVCR1, INSR, SLC2A4
lamellipodium 1 PIK3CA
Multi-pass membrane protein 1 SLC2A4
Synapse 1 CRH
cell surface 1 HAVCR1
Golgi apparatus 2 NOS3, PRKAA2
Golgi membrane 2 INS, NOS3
lysosomal membrane 1 GAA
neuronal cell body 1 PRKAA2
sarcolemma 1 SLC2A4
Cytoplasm, cytosol 1 ALOX5
Lysosome 3 GAA, INSR, TYR
Presynapse 1 SLC2A4
plasma membrane 8 GAA, GCG, HAVCR1, INSR, IRS1, NOS3, PIK3CA, SLC2A4
Membrane 4 GAA, INSR, PRKAA2, SLC2A4
axon 2 INSR, PRKAA2
caveola 3 INSR, IRS1, NOS3
extracellular exosome 6 AKR1B1, CA1, GAA, INSR, LCN2, SLC2A4
Lysosome membrane 1 GAA
endoplasmic reticulum 2 FOS, KEAP1
extracellular space 6 AKR1B1, ALOX5, CRH, GCG, INS, LCN2
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 5 ALOX5, NOS3, PIK3CA, SLC2A4, TYR
intercalated disc 1 PIK3CA
mitochondrion 1 AKR1B1
intracellular membrane-bounded organelle 3 GAA, IRS1, TYR
Single-pass type I membrane protein 3 HAVCR1, INSR, TYR
Secreted 5 CRH, GAA, GCG, INS, LCN2
extracellular region 6 ALOX5, CRH, GAA, GCG, INS, LCN2
neuronal cell body membrane 1 INSR
Cytoplasmic vesicle lumen 1 LCN2
centriolar satellite 1 KEAP1
motile cilium 1 HAVCR1
Nucleus membrane 1 ALOX5
nuclear membrane 1 ALOX5
external side of plasma membrane 2 INSR, SLC2A4
varicosity 1 CRH
multivesicular body 1 SLC2A4
T-tubule 1 SLC2A4
neuronal dense core vesicle lumen 1 CRH
perikaryon 1 CRH
Melanosome membrane 1 TYR
midbody 1 KEAP1
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
clathrin-coated pit 1 SLC2A4
Golgi-associated vesicle 1 TYR
Cytoplasm, perinuclear region 2 ALOX5, SLC2A4
Membrane raft 1 SLC2A4
sarcoplasmic reticulum 1 SLC2A4
nuclear speck 1 PRKAA2
Late endosome 1 INSR
receptor complex 1 INSR
chromatin 2 FOS, GABPA
cytoskeleton 1 NOS3
actin filament 1 KEAP1
Cul3-RING ubiquitin ligase complex 1 KEAP1
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
Endomembrane system 1 SLC2A4
endosome lumen 1 INS
Cytoplasmic vesicle membrane 1 SLC2A4
tertiary granule membrane 1 GAA
Melanosome 1 TYR
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 2 NOS3, PRKAA2
clathrin-coated vesicle 1 SLC2A4
trans-Golgi network transport vesicle 1 SLC2A4
ficolin-1-rich granule lumen 1 ALOX5
secretory granule lumen 3 ALOX5, GCG, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 GCG, INS
nuclear matrix 2 ALOX5, FOS
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
specific granule lumen 1 LCN2
endocytic vesicle membrane 1 NOS3
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
vesicle membrane 1 SLC2A4
protein-DNA complex 1 FOS
ficolin-1-rich granule membrane 1 GAA
dendrite membrane 1 INSR
nucleotide-activated protein kinase complex 1 PRKAA2
transcription factor AP-1 complex 1 FOS
[Glucagon-like peptide 1]: Secreted 1 GCG
inclusion body 1 KEAP1
insulin receptor complex 2 INSR, IRS1
Nucleus intermembrane space 1 ALOX5
autolysosome lumen 1 GAA
insulin-responsive compartment 1 SLC2A4
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
Cytoplasmic granule lumen 1 LCN2


文献列表

  • Taiki Fushimi, Chie Hirahata, Kento Hiroki, Yasuyuki Fujii, Vittorio Calabrese, Yoshitomo Suhara, Naomi Osakabe. Activation of transient receptor potential channels is involved in reactive oxygen species (ROS)-dependent regulation of blood flow by (-)-epicatechin tetramer cinnamtannin A2. Biochemical pharmacology. 2023 Jul; 214(?):115682. doi: 10.1016/j.bcp.2023.115682. [PMID: 37429424]
  • Yasuyuki Fujii, Jun Sakata, Fumitaka Sato, Kurumi Onishi, Yuki Yamato, Kazuki Sakata, Shu Taira, Hiroki Sato, Naomi Osakabe. Impact of short-term oral dose of cinnamtannin A2, an (-)-epicatechin tetramer, on spatial memory and adult hippocampal neurogenesis in mouse. Biochemical and biophysical research communications. 2021 12; 585(?):1-7. doi: 10.1016/j.bbrc.2021.11.021. [PMID: 34781055]
  • Yasuyuki Fujii, Yoshitomo Suhara, Yusuke Sukikara, Tomohiro Teshima, Yoshihisa Hirota, Kenjiro Yoshimura, Naomi Osakabe. Elucidation of the Interaction between Flavan-3-ols and Bovine Serum Albumin and Its Effect on Their In-Vitro Cytotoxicity. Molecules (Basel, Switzerland). 2019 Oct; 24(20):. doi: 10.3390/molecules24203667. [PMID: 31614668]
  • Tzong-Der Way, Shang-Jie Tsai, Chao-Min Wang, Yun-Lian Jhan, Chi-Tang Ho, Chang-Hung Chou. Cinnamtannin D1 from Rhododendron formosanum Induces Autophagy via the Inhibition of Akt/mTOR and Activation of ERK1/2 in Non-Small-Cell Lung Carcinoma Cells. Journal of agricultural and food chemistry. 2015 Dec; 63(48):10407-17. doi: 10.1021/acs.jafc.5b04375. [PMID: 26567590]
  • Yoko Yamashita, Masaaki Okabe, Midori Natsume, Hitoshi Ashida. Cinnamtannin A2, a tetrameric procyanidin, increases GLP-1 and insulin secretion in mice. Bioscience, biotechnology, and biochemistry. 2013; 77(4):888-91. doi: 10.1271/bbb.130095. [PMID: 23563558]
  • Abdelaaty A Shahat, Paul Cos, Tess De Bruyne, Sandra Apers, Fayza M Hammouda, Shams I Ismail, Safa Azzam, Magda Claeys, Etienne Goovaerts, Luc Pieters, Dirk Vanden Berghe, Arnold J Vlietinck. Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica. Planta medica. 2002 Jun; 68(6):539-41. doi: 10.1055/s-2002-32547. [PMID: 12094299]
  • Naomi Osakabe, Akiko Yasuda, Midori Natsume, Toshio Takizawa, Junji Terao, Kazuo Kondo. Catechins and their oligomers linked by C4 --> C8 bonds are major cacao polyphenols and protect low-density lipoprotein from oxidation in vitro. Experimental biology and medicine (Maywood, N.J.). 2002 Jan; 227(1):51-6. doi: 10.1177/153537020222700109. [PMID: 11788784]