Kelnac (BioDeep_00000009437)

 

Secondary id: BioDeep_00000858751

natural product


代谢物信息卡片


(2Z,6E)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-6-methylocta-2,6-diene-1,8-diol

化学式: C20H34O2 (306.2559)
中文名称: 谱劳诺托
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 29.45%

分子结构信息

SMILES: C/C(=C/CC/C(/C)=C/CC/C(=C/CC/C(/C)=C/CO)/CO)/C
InChI: InChI=1S/C20H34O2/c1-17(2)8-5-9-18(3)10-6-12-20(16-22)13-7-11-19(4)14-15-21/h8,10,13-14,21-22H,5-7,9,11-12,15-16H2,1-4H3/b18-10+,19-14+,20-13-

描述信息

A diterpenoid that is geranylgeraniol carrying an additional hydroxy substituent at position 18.
C78276 - Agent Affecting Digestive System or Metabolism > C29701 - Anti-ulcer Agent
D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents
D000890 - Anti-Infective Agents
Same as: D01803

同义名列表

8 个代谢物同义名

(2Z,6E)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-6-methylocta-2,6-diene-1,8-diol; (E,Z,E)-7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol; 18-Hydroxygeranylgeraniol; Plaunotolum; plaunotol; Kelnac; CS 684; Kelnac; Plaunotol



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • plaunotol biosynthesis: O2 + a reduced [NADPH-hemoprotein reductase] + geranylgeraniol ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + plaunotol

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

  • plaunotol biosynthesis: O2 + a reduced [NADPH-hemoprotein reductase] + geranylgeraniol ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + plaunotol

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

17 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 11 ANG, ANXA5, BCL2, BCL2L1, CASP3, CASP8, CASP9, ELANE, FPR1, MCL1, PTGS2
Peripheral membrane protein 2 ANXA5, PTGS2
Endoplasmic reticulum membrane 3 BCL2, PTGS2, TKT
Mitochondrion membrane 1 BCL2L1
Nucleus 7 ANG, BCL2, CASP3, CASP8, CASP9, MCL1, MPO
cytosol 10 ANG, ANXA5, BCL2, BCL2L1, CASP3, CASP8, CASP9, ELANE, MCL1, TKT
nuclear body 1 TKT
phagocytic vesicle 1 ELANE
centrosome 1 BCL2L1
nucleoplasm 5 CASP3, CASP8, MCL1, MPO, TKT
Cell membrane 2 FPR1, TKT
Cytoplasmic side 1 BCL2L1
lamellipodium 1 CASP8
Multi-pass membrane protein 2 ATP4A, FPR1
cell surface 2 ELANE, PLAU
glutamatergic synapse 1 CASP3
growth cone 1 ANG
mitochondrial inner membrane 1 BCL2L1
neuronal cell body 2 ANG, CASP3
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 BCL2L1
Lysosome 1 MPO
plasma membrane 4 ATP4A, FPR1, PLAU, TKT
synaptic vesicle membrane 1 BCL2L1
Membrane 6 ANXA5, ATP4A, BCL2, FPR1, HGF, MCL1
apical plasma membrane 2 ATP4A, TKT
caveola 1 PTGS2
extracellular exosome 6 ANXA5, ELANE, MPO, PLAU, TKT, VTN
endoplasmic reticulum 4 BCL2, BCL2L1, PTGS2, VTN
extracellular space 10 ANG, ATP4A, CXCL8, ELANE, GAST, HGF, MPO, PLAU, SCT, VTN
mitochondrion 5 BCL2, BCL2L1, CASP8, CASP9, MCL1
protein-containing complex 4 BCL2, CASP8, CASP9, PTGS2
intracellular membrane-bounded organelle 2 MPO, VTN
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TKT
Secreted 5 ANG, CXCL8, GAST, PLAU, VTN
extracellular region 10 ANG, ANXA5, CXCL8, ELANE, GAST, HGF, MPO, PLAU, SCT, VTN
Mitochondrion outer membrane 2 BCL2, BCL2L1
Single-pass membrane protein 3 BCL2, BCL2L1, MCL1
mitochondrial outer membrane 4 BCL2, BCL2L1, CASP8, MCL1
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 1 BCL2L1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 BCL2L1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 3 BCL2, BCL2L1, MCL1
nuclear membrane 2 BCL2, BCL2L1
external side of plasma membrane 2 ANXA5, PLAU
actin cytoskeleton 2 ANG, TKT
nucleolus 1 ANG
vesicle 1 TKT
Apical cell membrane 1 ATP4A
Cell projection, lamellipodium 1 CASP8
pore complex 1 BCL2
focal adhesion 3 ANXA5, PLAU, TKT
Peroxisome 1 TKT
basement membrane 2 ANG, VTN
collagen-containing extracellular matrix 3 ANXA5, ELANE, VTN
secretory granule 2 ELANE, MPO
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 TKT
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
Chromosome 1 ANG
cytoskeleton 1 CASP8
Secreted, extracellular space 1 VTN
Nucleus, nucleolus 1 ANG
blood microparticle 1 VTN
myosin complex 1 MCL1
Nucleus, nucleoplasm 1 MCL1
specific granule membrane 1 PLAU
tertiary granule membrane 1 PLAU
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
cell body 1 CASP8
myelin sheath 1 BCL2
azurophil granule 1 MPO
secretory granule membrane 1 FPR1
Golgi lumen 1 VTN
endoplasmic reticulum lumen 1 PTGS2
transcription repressor complex 1 ELANE
platelet alpha granule lumen 1 HGF
specific granule lumen 1 ELANE
endocytic vesicle 1 ANG
azurophil granule membrane 1 FPR1
azurophil granule lumen 2 ELANE, MPO
serine-type endopeptidase complex 1 PLAU
apoptosome 1 CASP9
vesicle membrane 1 ANXA5
phagocytic vesicle lumen 1 MPO
ficolin-1-rich granule membrane 1 FPR1
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
serine protease inhibitor complex 1 PLAU
Cytoplasmic vesicle, phagosome 1 ELANE
protein complex involved in cell-matrix adhesion 2 PLAU, VTN
peptidase inhibitor complex 1 VTN
angiogenin-PRI complex 1 ANG
Parasitophorous vacuole 1 VTN
alphav-beta3 integrin-vitronectin complex 1 VTN
rough endoplasmic reticulum lumen 1 VTN
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
potassium:proton exchanging ATPase complex 1 ATP4A
caspase complex 1 CASP9
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1


文献列表

  • Siriluk Sintupachee, Nattaya Ngamrojanavanich, Worapan Sitthithaworn, Wanchai De-Eknamkul. Molecular cloning, bacterial expression and functional characterisation of cytochrome P450 monooxygenase, CYP97C27, and NADPH-cytochrome P450 reductase, CPR I, from Croton stellatopilosus Ohba. Plant science : an international journal of experimental plant biology. 2014 Dec; 229(?):131-141. doi: 10.1016/j.plantsci.2014.09.001. [PMID: 25443840]
  • Chatchai Chaotham, Songpol Chivapat, Anan Chaikitwattana, Wanchai De-Eknamkul. Acute and chronic oral toxicity of a partially purified plaunotol extract from Croton stellatopilosus Ohba. BioMed research international. 2013; 2013(?):303162. doi: 10.1155/2013/303162. [PMID: 24286075]
  • Neyres Zinia Taveira De Jesus, Heloina de Souza Falcão, Isis Fernandes Gomes, Thiago Jose de Almeida Leite, Gedson Rodrigues de Morais Lima, Jose Maria Barbosa-Filho, Josean Fechine Tavares, Marcelo Sobral da Silva, Petrônio Filgueiras de Athayde-Filho, Leonia Maria Batista. Tannins, peptic ulcers and related mechanisms. International journal of molecular sciences. 2012; 13(3):3203-3228. doi: 10.3390/ijms13033203. [PMID: 22489149]
  • Prasob-orn Rinthong, Shu Zhu, Katsuko Komatsu, Suchart Chanama, Wanchai De-Eknamkul. Genetic variation of Croton stellatopilosus Ohba based on non-coding DNA sequences of ITS, trnK and trnL-F regions. Journal of natural medicines. 2011 Jul; 65(3-4):641-5. doi: 10.1007/s11418-011-0536-8. [PMID: 21499847]
  • Siribang-on Piboonniyom Khovidhunkit, Nadiya Yingsaman, Kongtawat Chairachvit, Rudee Surarit, Pornpoj Fuangtharnthip, Amorn Petsom. In vitro study of the effects of plaunotol on oral cell proliferation and wound healing. Journal of Asian natural products research. 2011 Feb; 13(2):149-59. doi: 10.1080/10286020.2010.546790. [PMID: 21279879]
  • Francesco Emanuelli, Juri Battilana, Laura Costantini, Loïc Le Cunff, Jean-Michel Boursiquot, Patrice This, Maria S Grando. A candidate gene association study on muscat flavor in grapevine (Vitis vinifera L.). BMC plant biology. 2010 Nov; 10(?):241. doi: 10.1186/1471-2229-10-241. [PMID: 21062440]
  • Naoyuki Yoshikawa, Jun Yamada, Nelson H Tsuno, Yurai Okaji, Kazushige Kawai, Takeshi Tsuchiya, Satomi Yoneyama, Junichiro Tanaka, Yasutaka Shuno, Takeshi Nishikawa, Hirokazu Nagawa, Noriko Oshima, Koki Takahashi. Plaunotol and geranylgeraniol induce caspase-mediated apoptosis in colon cancer. The Journal of surgical research. 2009 May; 153(2):246-53. doi: 10.1016/j.jss.2008.04.021. [PMID: 18805546]
  • Juraithip Wungsintaweekul, Tanawan Sirisuntipong, Damrong Kongduang, Thanaisawan Losuphanporn, Anan Ounaroon, Pimpimon Tansakul, Wanchai De-Eknamkul. Transcription profiles analysis of genes encoding 1-deoxy-D-xylulose 5-phosphate synthase and 2C-methyl-D-erythritol 4-phosphate synthase in plaunotol biosynthesis from Croton stellatopilosus. Biological & pharmaceutical bulletin. 2008 May; 31(5):852-6. doi: 10.1248/bpb.31.852. [PMID: 18451506]
  • Jun Yamada, Kazushige Kawai, Nelson H Tsuno, Joji Kitayama, Takeshi Tsuchiya, Satomi Yoneyama, Masahiro Asakage, Yurai Okaji, Koki Takahashi, Hirokazu Nagawa. Plaunotol induces apoptosis of gastric cancer cells. Planta medica. 2007 Aug; 73(10):1068-73. doi: 10.1055/s-2007-981578. [PMID: 17691055]
  • Natsajee Nualkaew, Wanchai De-Eknamkul, Toni M Kutchan, Meinhart H Zenk. Membrane-bound geranylgeranyl diphosphate phosphatases: purification and characterization from Croton stellatopilosus leaves. Phytochemistry. 2006 Aug; 67(15):1613-20. doi: 10.1016/j.phytochem.2005.12.014. [PMID: 16445953]
  • Hai ying Fu, Yuki Yabe, Kayoko Asahi, Yujiro Hayashi, Hiroaki Murata, Hiroshi Eguchi, Masahiko Tsujii, Shingo Tsuji, Sunao Kawano. (2E,6Z,10E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol (Plaunotol) increases cyclooxygenase-2 expression via nuclear factor kappaB and cyclic AMP response element in rat gastric epithelial cells. European journal of pharmacology. 2005 Nov; 524(1-3):38-43. doi: 10.1016/j.ejphar.2005.09.044. [PMID: 16253229]
  • Yoshiji Ohta, Yoshio Kamiya, Yoichiro Imai, Tomiyasu Arisawa, Hiroshi Nakano. Plaunotol prevents the progression of acute gastric mucosal lesions induced by compound 48/80, a mast cell degranulator, in rats. Pharmacology. 2005 Jul; 74(4):182-92. doi: 10.1159/000085388. [PMID: 15855831]
  • H Tamura, H Tokushima, M Murakawa, O Matsumura, S Itoyama, S Sekine, H Hirose, T Mitarai, K Isoda. Eradication of Helicobacter pylori in patients with end-stage renal disease under dialysis treatment. American journal of kidney diseases : the official journal of the National Kidney Foundation. 1997 Jan; 29(1):86-90. doi: 10.1016/s0272-6386(97)90012-3. [PMID: 9002534]
  • K Murakami, T Fujioka, A Nishizono, J Nagai, M Tokieda, R Kodama, T Kubota, M Nasu. Atopic dermatitis successfully treated by eradication of Helicobacter pylori. Journal of gastroenterology. 1996 Nov; 31 Suppl 9(?):77-82. doi: . [PMID: 8959527]
  • H Tokushima, H Tamura, O Matsumura, M Murakawa, Y Itakura, S Itoyama, T Mitarai, K Isoda. [Eradication of Helicobacter pylori in patients with end-stage renal disease undergoing dialysis treatment]. Nihon Jinzo Gakkai shi. 1996 Aug; 38(8):349-55. doi: . [PMID: 8828354]
  • H Kaneko, T Mitsuma, H Nagai, M Harada, H Kotera, A Furusawa, K Morise. Effect of plaunotol on hypergastrinemia induced by long-term omeprazole administration in humans. Digestive diseases and sciences. 1995 Jan; 40(1):160-5. doi: 10.1007/bf02063960. [PMID: 7821104]
  • K Shiratori, S Watanabe, T Takeuchi. Role of endogenous prostaglandins in secretin- and plaunotol-induced inhibition of gastric acid secretion in the rat. The American journal of gastroenterology. 1993 Jan; 88(1):84-9. doi: . [PMID: 8420279]
  • T Takeuchi, K Shiratori, S Watanabe, J H Chang, Y Moriyoshi, K Shimizu. Secretin as a potential mediator of antiulcer actions of mucosal protective agents. Journal of clinical gastroenterology. 1991; 13 Suppl 1(?):S83-7. doi: 10.1097/00004836-199112001-00014. [PMID: 1940202]
  • K Shiratori, S Watanabe, T Takeuchi, K Shimizu. Plaunotol inhibits postprandial gastrin release by its unique secretin-releasing action in humans. Digestive diseases and sciences. 1990 Sep; 35(9):1140-5. doi: 10.1007/bf01537587. [PMID: 2390929]
  • K Shiratori, S Watanabe, T Takeuchi, J H Chang, Y Moriyoshi. Effect of plaunotol on release of plasma secretin and pancreatic exocrine secretion in humans. Pancreas. 1989; 4(3):323-8. doi: 10.1097/00006676-198906000-00008. [PMID: 2471968]
  • J H Chang, S Watanabe, K Shiratori, Y Moriyoshi, T Takeuchi. Plaunotol stimulates endogenous secretin release and exocrine pancreatic secretion in rats. Digestion. 1989; 44(3):142-7. doi: 10.1159/000199903. [PMID: 2483390]
  • . . . . doi: . [PMID: 19782428]