4alpha-Phorbol (BioDeep_00000174621)

   

human metabolite blood metabolite natural product


代谢物信息卡片


1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-5-one

化学式: C20H28O6 (364.1886)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=CC2C(O)(CC(CO)=CC3C4C(C)(C)C4(O)C(O)C(C)C32O)C1=O
InChI: InChI=1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3



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相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

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INOH(0)

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10 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 7 ANG, GFAP, ITPR3, MAPK3, MYLK, PLA2G12A, PRKX
Endosome membrane 1 CLCN5
Endoplasmic reticulum membrane 1 ITPR3
Nucleus 6 ANG, MAPK3, MPO, PLCZ1, PRKX, RFC2
cytosol 7 ANG, CLCN5, GFAP, MAPK3, MYLK, PLCZ1, PRKCQ
nucleoplasm 7 CD2, ITPR3, MAPK3, MPO, PLCZ1, PRKX, RFC2
Cell membrane 4 CD2, CLCN5, TRPV1, TRPV4
Cleavage furrow 1 MYLK
lamellipodium 2 MYLK, TRPV4
ruffle membrane 1 TRPV4
Multi-pass membrane protein 4 CLCN5, ITPR3, TRPV1, TRPV4
Golgi apparatus membrane 1 CLCN5
Synapse 1 MYLK
cell surface 2 CD2, TRPV4
glutamatergic synapse 1 MAPK3
Golgi apparatus 3 CD2, CLCN5, MAPK3
Golgi membrane 2 CLCN5, INS
growth cone 2 ANG, TRPV4
lysosomal membrane 2 CLCN5, EGF
neuronal cell body 3 ANG, ITPR3, TRPV1
synaptic vesicle 1 CLCN5
Lysosome 1 MPO
plasma membrane 10 CD2, CLCN5, EGF, F2, ITPR3, MAPK3, MYLK, PRKCQ, TRPV1, TRPV4
Membrane 5 CLCN5, EGF, ITPR3, TRPV1, TRPV4
apical plasma membrane 1 TRPV4
brush border 1 ITPR3
caveola 1 MAPK3
extracellular exosome 3 EGF, F2, MPO
endoplasmic reticulum 2 ITPR3, TRPV4
extracellular space 6 ANG, EGF, F2, IL2, INS, MPO
perinuclear region of cytoplasm 1 PLCZ1
adherens junction 1 TRPV4
mitochondrion 1 MAPK3
protein-containing complex 1 CD2
intracellular membrane-bounded organelle 1 MPO
filopodium 1 TRPV4
pronucleus 1 PLCZ1
Single-pass type I membrane protein 1 CD2
Secreted 5 ANG, F2, IL2, INS, PLA2G12A
extracellular region 8 ANG, CD2, EGF, F2, IL2, INS, MPO, PLA2G12A
cytoplasmic side of plasma membrane 1 CD2
astrocyte end-foot 1 GFAP
Cell projection, cilium 1 TRPV4
centriolar satellite 1 PRKCQ
external side of plasma membrane 2 CD2, TRPV1
actin cytoskeleton 2 ANG, MYLK
nucleolus 3 ANG, ITPR3, PLCZ1
Early endosome 2 CLCN5, MAPK3
apical part of cell 2 CLCN5, ITPR3
cell-cell junction 1 CD2
postsynaptic membrane 1 TRPV1
Apical cell membrane 1 TRPV4
Cell projection, lamellipodium 1 MYLK
Cytoplasm, perinuclear region 1 PLCZ1
Cell junction, focal adhesion 1 MAPK3
focal adhesion 2 MAPK3, TRPV4
GABA-ergic synapse 1 TRPV1
Cell junction, adherens junction 1 TRPV4
basement membrane 1 ANG
sarcoplasmic reticulum 1 ITPR3
collagen-containing extracellular matrix 1 F2
secretory granule 1 MPO
intermediate filament 1 GFAP
nuclear outer membrane 1 ITPR3
Postsynaptic cell membrane 1 TRPV1
Late endosome 1 MAPK3
receptor complex 1 ITPR3
Cell projection, neuron projection 1 TRPV1
cilium 1 TRPV4
cell projection 1 GFAP
Chromosome 1 ANG
cytoskeleton 1 MAPK3
Nucleus, nucleolus 1 ANG
blood microparticle 1 F2
nuclear envelope 1 MAPK3
endosome lumen 1 INS
Membrane, caveola 1 MAPK3
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
cell body 1 GFAP
pseudopodium 1 MAPK3
intermediate filament cytoskeleton 1 GFAP
stress fiber 1 MYLK
azurophil granule 1 MPO
secretory granule lumen 1 INS
secretory granule membrane 1 ITPR3
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 3 F2, INS, MAPK3
cortical actin cytoskeleton 1 TRPV4
platelet alpha granule lumen 1 EGF
endocytic vesicle 1 ANG
transport vesicle 1 INS
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
clathrin-coated endocytic vesicle membrane 1 EGF
phagocytic vesicle lumen 1 MPO
Cytoplasm, cytoskeleton, stress fiber 1 MYLK
platelet dense tubular network membrane 1 ITPR3
cytoplasmic microtubule 1 TRPV4
[Isoform 1]: Cell membrane 1 TRPV4
Cytoplasmic vesicle, secretory vesicle membrane 1 ITPR3
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
cytoplasmic side of lysosomal membrane 1 GFAP
[Isoform 2]: Endoplasmic reticulum 1 TRPV4
transport vesicle membrane 1 ITPR3
angiogenin-PRI complex 1 ANG
sperm head 1 PLCZ1
[Isoform 5]: Cell membrane 1 TRPV4
cytoplasmic side of endoplasmic reticulum membrane 1 ITPR3
Ctf18 RFC-like complex 1 RFC2
DNA replication factor C complex 1 RFC2
[Isoform 4]: Endoplasmic reticulum 1 TRPV4
[Isoform 6]: Endoplasmic reticulum 1 TRPV4


文献列表

  • Jie-Ping Fan, Ban-Tian He, Yi Gao, Chun-Fang Xie, Hui-Ping Chen, Hai-Long Peng. Biphasic alcoholysis coupled with high-speed countercurrent chromatography for high performance on separating phorbol from Croton tiglium Linn extracts. Journal of separation science. 2023 Apr; 46(8):e2200984. doi: 10.1002/jssc.202200984. [PMID: 36795010]
  • Abbes Benmerache, Abdulmagid Alabdul Magid, Amira Labed, Ahmed Kabouche, Laurence Voutquenne-Nazabadioko, Jane Hubert, Hamid Morjani, Zahia Kabouche. Isolation and characterisation of cytotoxic compounds from Euphorbia clementei Boiss. Natural product research. 2017 Sep; 31(18):2091-2098. doi: 10.1080/14786419.2016.1277345. [PMID: 28068859]
  • Takefumi Kamakura, Makoto Kondo, Yoshihisa Koyama, Yukiko Hanada, Yusuke Ishida, Yukiko Nakamura, Takahiro Yamada, Yasumitsu Takimoto, Tadashi Kitahara, Yoshiyuki Ozono, Arata Horii, Takao Imai, Hidenori Inohara, Shoichi Shimada. Functional Expression of an Osmosensitive Cation Channel, Transient Receptor Potential Vanilloid 4, in Rat Vestibular Ganglia. Audiology & neuro-otology. 2016; 21(4):268-274. doi: 10.1159/000449238. [PMID: 27705979]
  • Ammar Bader, Rosa M Giner, Francesca Martini, Guillermo R Schinella, José L Ríos, Alessandra Braca, José M Prieto. Modulation of COX, LOX and NFκB activities by Xanthium spinosum L. root extract and ziniolide. Fitoterapia. 2013 Dec; 91(?):284-289. doi: 10.1016/j.fitote.2013.09.015. [PMID: 24090994]
  • Beth Ndunda, Moses K Langat, John M Wanjohi, Jacob O Midiwo, Leonidah O Kerubo. Alienusolin, a new 4α-deoxyphorbol ester derivative, and crotonimide C, a new glutarimide alkaloid from the Kenyan Croton alienus. Planta medica. 2013 Dec; 79(18):1762-6. doi: 10.1055/s-0033-1351044. [PMID: 24356872]
  • Rui Wang, Jian-Yong Li, Huan-Yang Qi, Yan-Ping Shi. Two new tigliane diterpene esters from the flower buds of Daphne genkwa. Journal of Asian natural products research. 2013; 15(5):502-6. doi: 10.1080/10286020.2013.786703. [PMID: 23600859]
  • Emad Afrasiabi, Janiina Ahlgren, Nina Bergelin, Kid Törnquist. Phorbol 12-myristate 13-acetate inhibits FRO anaplastic human thyroid cancer cell proliferation by inducing cell cycle arrest in G1/S phase: evidence for an effect mediated by PKCdelta. Molecular and cellular endocrinology. 2008 Sep; 292(1-2):26-35. doi: 10.1016/j.mce.2008.04.018. [PMID: 18541361]
  • Francesco Buonocore, Angelo Libertini, Daniela Prugnoli, Massimo Mazzini, Giuseppe Scapigliati. Production and characterization of a continuous embryonic cell line from sea bass (Dicentrarchus labrax L.). Marine biotechnology (New York, N.Y.). 2006 Jan; 8(1):80-5. doi: 10.1007/s10126-005-5032-2. [PMID: 16249966]
  • Lankupalle D Jayanthi, Devadoss J Samuvel, Randy D Blakely, Sammanda Ramamoorthy. Evidence for biphasic effects of protein kinase C on serotonin transporter function, endocytosis, and phosphorylation. Molecular pharmacology. 2005 Jun; 67(6):2077-87. doi: 10.1124/mol.104.009555. [PMID: 15774771]
  • R W Moore, D Y Caldwell, L R Berghman, D J Caldwell, A P McElroy, J A Byrd, B M Hargis. Effect of bursal anti-steroidogenic peptide and immunoglobulin G on neonatal chicken B-lymphocyte proliferation. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2003 Mar; 134(3):291-302. doi: 10.1016/s1532-0456(02)00208-9. [PMID: 12643976]
  • Yukio Miyata, Koji Okada, Shun Ishibashi, Yasushi Asano, Shigeaki Muto. P-gp-induced modulation of regulatory volume increase occurs via PKC in mouse proximal tubule. American journal of physiology. Renal physiology. 2002 Jan; 282(1):F65-76. doi: 10.1152/ajprenal.0036.2001. [PMID: 11739114]
  • D Trotti, J B Peng, J Dunlop, M A Hediger. Inhibition of the glutamate transporter EAAC1 expressed in Xenopus oocytes by phorbol esters. Brain research. 2001 Sep; 914(1-2):196-203. doi: 10.1016/s0006-8993(01)02802-5. [PMID: 11578612]
  • G M Daniels, S G Amara. Regulated trafficking of the human dopamine transporter. Clathrin-mediated internalization and lysosomal degradation in response to phorbol esters. The Journal of biological chemistry. 1999 Dec; 274(50):35794-801. doi: 10.1074/jbc.274.50.35794. [PMID: 10585462]
  • B Sampaio-Maia, R Gomes, P Soares-da-Silva. P-glycoprotein phosphorylation/dephosphorylation and cellular accumulation of L-DOPA in LLC-GA5 Col300 cells. Journal of autonomic pharmacology. 1999 Jun; 19(3):173-9. doi: 10.1046/j.1365-2680.1999.00131.x. [PMID: 10511474]
  • K M Noh, Y H Kim, J Y Koh. Mediation by membrane protein kinase C of zinc-induced oxidative neuronal injury in mouse cortical cultures. Journal of neurochemistry. 1999 Apr; 72(4):1609-16. doi: 10.1046/j.1471-4159.1999.721609.x. [PMID: 10098868]
  • G Frindt, L G Palmer, E E Windhager. Feedback regulation of Na channels in rat CCT. IV. Mediation by activation of protein kinase C. The American journal of physiology. 1996 Feb; 270(2 Pt 2):F371-6. doi: 10.1152/ajprenal.1996.270.2.f371. [PMID: 8779899]
  • W J McGuire, J L Juengel, G D Niswender. Protein kinase C second messenger system mediates the antisteroidogenic effects of prostaglandin F2 alpha in the ovine corpus luteum in vivo. Biology of reproduction. 1994 Oct; 51(4):800-6. doi: 10.1095/biolreprod51.4.800. [PMID: 7819462]
  • A M Paradiso. Identification of Na(+)-H+ exchange in human normal and cystic fibrotic ciliated airway epithelium. The American journal of physiology. 1992 Jun; 262(6 Pt 1):L757-64. doi: 10.1152/ajplung.1992.262.6.l757. [PMID: 1319688]
  • F Farzaneh, A Entwistle, R J Zalin. Protein kinase C mediates the hormonally regulated plasma membrane fusion of avian embryonic skeletal muscle. Experimental cell research. 1989 Mar; 181(1):298-304. doi: 10.1016/0014-4827(89)90204-8. [PMID: 2917608]
  • D W Kamp, K D Bauer, D B Rubin, M M Dunn. Tumor-promoting phorbol esters inhibit monocyte adherence to endothelial cells. Journal of applied physiology (Bethesda, Md. : 1985). 1989 Jan; 66(1):437-42. doi: 10.1152/jappl.1989.66.1.437. [PMID: 2917948]
  • S R Slivka, P A Insel. Phorbol ester and neomycin dissociate bradykinin receptor-mediated arachidonic acid release and polyphosphoinositide hydrolysis in Madin-Darby canine kidney cells. Evidence that bradykinin mediates noninterdependent activation of phospholipases A2 and C. The Journal of biological chemistry. 1988 Oct; 263(29):14640-7. doi: . [PMID: 2902085]
  • S Amir. TPA (12-O-tetradecanoylphorbol-13-acetate) enhances the central hypoglycemic action of thyrotropin-releasing hormone in mice. Brain research. 1988 May; 450(1-2):369-72. doi: 10.1016/0006-8993(88)91577-6. [PMID: 3135916]
  • P A Craven, M C Patterson, F R DeRubertis. Role for protein kinase C in the modulation of glomerular PGE2 production by angiotensin II. Biochemical and biophysical research communications. 1988 May; 152(3):1481-9. doi: 10.1016/s0006-291x(88)80453-4. [PMID: 3163921]
  • M C Chobanian, M R Hammerman. Phorbol esters inhibit ammoniagenesis and gluconeogenesis in proximal tubular segments. The American journal of physiology. 1987 Jun; 252(6 Pt 2):F1073-9. doi: 10.1152/ajprenal.1987.252.6.f1073. [PMID: 3473939]
  • J Eichberg, P N de Graan, L H Schrama, W H Gispen. Dioctanoylglycerol and phorbol diesters enhance phosphorylation of phosphoprotein B-50 in native synaptic plasma membranes. Biochemical and biophysical research communications. 1986 May; 136(3):1007-12. doi: 10.1016/0006-291x(86)90433-x. [PMID: 2941012]
  • J Blenis, R L Erikson. Stimulation of ribosomal protein S6 kinase activity by pp60v-src or by serum: dissociation from phorbol ester-stimulated activity. Proceedings of the National Academy of Sciences of the United States of America. 1986 Mar; 83(6):1733-7. doi: 10.1073/pnas.83.6.1733. [PMID: 3081899]
  • S S Kadner, J Katz, M Levitz, T H Finlay. The 65-kDa phorbol-diester hydrolase in mouse plasma is esterase 1 and is immunologically distinct from the 56-kDa phorbol-diester hydrolase in mouse liver. The Journal of biological chemistry. 1985 Dec; 260(29):15604-9. doi: . [PMID: 3864781]
  • A Tanabe, T B Nielsen, C S Rani, J B Field. Thyroid cell responses to thyrotropin and 12-O-tetradecanoyl-phorbol-13-acetate: translocation of protein kinase C and phosphorylation of thyroid cell polypeptide substrates. Archives of biochemistry and biophysics. 1985 Nov; 243(1):92-9. doi: 10.1016/0003-9861(85)90776-3. [PMID: 2415065]
  • N Morinaga, T Kuwata. Enhancement by phorbol esters of cell growth inhibiting action of interferon. Journal of interferon research. 1984; 4(4):543-51. doi: 10.1089/jir.1984.4.543. [PMID: 6501944]
  • S Nomura, N Shobu, M Oishi. Tumor promoter 12-O-tetradecanoylphorbol 13-acetate stimulates simian virus 40 induction by DNA-damaging agents and tumor initiators. Molecular and cellular biology. 1983 May; 3(5):757-60. doi: 10.1128/mcb.3.5.757-760.1983. [PMID: 6306445]