Phorbol (BioDeep_00000000402)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


1,1a,1b,4,4a,7a,7b,8,9,9a-Decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-

化学式: C20H28O6 (364.1886)
中文名称: 佛波, 佛波醇, 伏波醇
谱图信息: 最多检出来源 Viridiplantae(plant) 34.93%

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

描述信息

Phorbol is a white solid. (NTP, 1992)
Phorbol is a diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(beta), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions. It is a tetracyclic diterpenoid, an enone, a cyclic ketone, a tertiary alcohol and a tertiary alpha-hydroxy ketone. It derives from a hydride of a tigliane.
Phorbol is a natural product found in Euphorbia tirucalli, Croton tiglium, and Rehmannia glutinosa with data available.
Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. Phorbol was first isolated in 1934 as the hydrolysis product of croton oil, which is derived from the seeds of the purging croton, Croton tiglium. The structure of phorbol was determined in 1967. It is very soluble in most polar organic solvents, as well as in water.
Phorbol is a highly toxic diterpene, whose esters have important biological properties.
Phorbol is a highly toxic diterpene, whose esters have important biological properties.

同义名列表

37 个代谢物同义名

1,1a,1b,4,4a,7a,7b,8,9,9a-Decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-; 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,6,8-tetramethyl-, (1aR-(1aalpha,1beta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-; 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-beta,1b-alpha,4,4a,7a-beta,7b,8,9,9a-decahydro-4a-alpha,7b-alpha,9-beta,9a-alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-alpha-tetramethyl-; 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4abeta,7balpha,9beta,9a alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetramethyl-, (+)-; 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-; 5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-; (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one; (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-Tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1b,4,4a,7a,7b,8,9,9a-octahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-5(1aH)-one; (1AR,1BS,4AR,7AS,7BS,8R,9R,9AS)-1,1A,1B,4,4A,7A,7B,8,9,9A-DECAHYDRO-4A,7B,9,9A-TETRAHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-5H-CYCLOPROPA(3,4)BENZ(1,2-E)AZULEN-5-ONE; (1S,2S,6R,10S,11R,13S,14R,15R)-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; phorbol, (1aR-(1aalpha,1bbeta,4aalpha,7aalpha,7balpha,8alpha,9beta,9bbeta))-isomer; 4beta,9alpha,12beta,13alpha,20-Pentahydroxytiglia-1,6-dien-3-one; 5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLECITRATESALT; 4,9,12-beta,13,20-Pentahydroxy-1,6-tigliadien-3-on; 4,9,12beta,13,20-pentahydroxytiglia-1,6-dien-3-one; 4,9,12beta,13,20-pentahydroxy-1,6-tigliadien-3-on; tetrahydroxy-(hydroxymethyl)-tetramethyl-[?]one; QGVLYPPODPLXMB-UBTYZVCOSA-N; 4-.beta.-Phorbol; 4-alpha-phorbol; UNII-XUZ76S9127; PHORBOL [HSDB]; 4alpha-phorbol; 4-beta-Phorbol; 4.b.-Phorbol; PHORBOL [MI]; beta-phorbol; (+)-phorbol; SMP2_000151; XUZ76S9127; isophorbol; 4b-phorbol; 1ST174301; 4-Phorbol; Phorbol; 4β-Phorbol; Phorbol



数据库引用编号

22 个数据库交叉引用编号

分类词条

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。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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PharmGKB(0)

33 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 8 EGFR, HPGDS, MAPK14, MAPK8, ODC1, PRKCA, PRKCD, PTGS2
Peripheral membrane protein 3 PRKCA, PRKCD, PTGS2
Endosome membrane 2 EGFR, TFRC
Endoplasmic reticulum membrane 3 CD4, EGFR, PTGS2
Mitochondrion membrane 1 PRKCA
Nucleus 6 EGFR, JUND, MAPK14, MAPK8, PRKCA, PRKCD
cytosol 8 HPGDS, IL1B, MAPK14, MAPK8, ODC1, PRKCA, PRKCD, PRKCQ
mitochondrial membrane 1 PRKCA
nucleoplasm 6 HPGDS, JUND, MAPK14, MAPK8, PRKCA, PRKCD
RNA polymerase II transcription regulator complex 1 JUND
Cell membrane 7 CD4, EGFR, ITGAM, PRKCA, PRKCD, TFRC, TNF
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 1 CACNA1I
Synapse 2 MAPK8, PRKCD
cell junction 1 EGFR
cell surface 5 EGFR, ITGAM, PLAU, TFRC, TNF
glutamatergic synapse 3 EGFR, MAPK14, TFRC
Golgi membrane 1 EGFR
neuronal cell body 1 TNF
Cytoplasm, cytosol 1 IL1B
Lysosome 1 IL1B
endosome 2 EGFR, TFRC
plasma membrane 12 CACNA1I, CD4, EGFR, IFNLR1, IGHE, ITGAM, PLAU, PRKCA, PRKCD, PRKCQ, TFRC, TNF
Membrane 7 CACNA1I, EGFR, IFNLR1, ITGAM, PRKCA, PRKCD, TFRC
apical plasma membrane 1 EGFR
axon 1 MAPK8
basolateral plasma membrane 2 EGFR, TFRC
caveola 1 PTGS2
extracellular exosome 5 ITGAM, PLAU, PRKCA, PRKCD, TFRC
endoplasmic reticulum 3 PRKCA, PRKCD, PTGS2
extracellular space 8 EGFR, IGHE, IL1B, IL4, ITGAM, PLAU, TFRC, TNF
perinuclear region of cytoplasm 4 EGFR, PRKCA, PRKCD, TFRC
mitochondrion 3 MAPK14, PRKCA, PRKCD
protein-containing complex 2 EGFR, PTGS2
intracellular membrane-bounded organelle 2 HPGDS, TFRC
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 5 CD4, EGFR, IFNLR1, IGHE, ITGAM
Secreted 3 IL1B, IL4, PLAU
extracellular region 8 IGHE, IL1B, IL4, MAPK14, PLAU, PRKCD, TFRC, TNF
transcription regulator complex 1 JUND
centriolar satellite 1 PRKCQ
nuclear membrane 1 EGFR
external side of plasma membrane 5 CD4, ITGAM, PLAU, TFRC, TNF
Extracellular vesicle 1 TFRC
cytoplasmic vesicle 1 TFRC
Early endosome 2 CD4, TFRC
cell-cell junction 1 PRKCD
clathrin-coated pit 1 TFRC
recycling endosome 2 TFRC, TNF
Single-pass type II membrane protein 2 TFRC, TNF
Cytoplasm, perinuclear region 1 PRKCD
Membrane raft 4 CD4, EGFR, ITGAM, TNF
focal adhesion 2 EGFR, PLAU
intracellular vesicle 1 EGFR
secretory granule 1 IL1B
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 EGFR
neuron projection 2 PRKCD, PTGS2
ciliary basal body 1 PRKCA
chromatin 1 JUND
IgE immunoglobulin complex 1 IGHE
phagocytic cup 1 TNF
spindle pole 1 MAPK14
blood microparticle 1 TFRC
[Isoform 2]: Cell membrane 1 IGHE
Recycling endosome membrane 1 TFRC
Endomembrane system 1 PRKCD
specific granule membrane 2 ITGAM, PLAU
tertiary granule membrane 2 ITGAM, PLAU
Melanosome 1 TFRC
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
plasma membrane raft 1 ITGAM
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
HFE-transferrin receptor complex 1 TFRC
endoplasmic reticulum lumen 2 CD4, PTGS2
nuclear matrix 1 PRKCD
transcription repressor complex 1 JUND
voltage-gated calcium channel complex 1 CACNA1I
Secreted, extracellular exosome 1 IL1B
azurophil granule lumen 1 PRKCD
serine-type endopeptidase complex 1 PLAU
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
clathrin-coated endocytic vesicle membrane 3 CD4, EGFR, TFRC
Synapse, synaptosome 1 PRKCD
basal dendrite 1 MAPK8
serine protease inhibitor complex 1 PLAU
postsynaptic recycling endosome membrane 1 TFRC
integrin complex 1 ITGAM
[Isoform 3]: Cell membrane 1 IGHE
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
protein complex involved in cell-matrix adhesion 1 PLAU
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 1 CD4
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
[Transferrin receptor protein 1, serum form]: Secreted 1 TFRC
alphav-beta3 integrin-PKCalpha complex 1 PRKCA
integrin alphaM-beta2 complex 1 ITGAM
endolysosome 1 PRKCD
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
  • Mélanie Bourjot, Leen Delang, Van Hung Nguyen, Johan Neyts, Françoise Guéritte, Pieter Leyssen, Marc Litaudon. Prostratin and 12-O-tetradecanoylphorbol 13-acetate are potent and selective inhibitors of Chikungunya virus replication. Journal of natural products. 2012 Dec; 75(12):2183-7. doi: 10.1021/np300637t. [PMID: 23215460]
  • Yoon-Young Sung, Won-Kyung Yang, A Yeong Lee, Dong-Seon Kim, Kyoung Jin Nho, Young Sang Kim, Ho Kyoung Kim. Topical application of an ethanol extract prepared from Illicium verum suppresses atopic dermatitis in NC/Nga mice. Journal of ethnopharmacology. 2012 Oct; 144(1):151-9. doi: 10.1016/j.jep.2012.08.042. [PMID: 22971899]
  • Young Sun Han, Myung-Suk Kim, Jae-Kwan Hwang. Macelignan inhibits histamine release and inflammatory mediator production in activated rat basophilic leukemia mast cells. Inflammation. 2012 Oct; 35(5):1723-31. doi: 10.1007/s10753-012-9490-1. [PMID: 22729280]
  • Christopher L German, Glen R Hanson, Annette E Fleckenstein. Amphetamine and methamphetamine reduce striatal dopamine transporter function without concurrent dopamine transporter relocalization. Journal of neurochemistry. 2012 Oct; 123(2):288-97. doi: 10.1111/j.1471-4159.2012.07875.x. [PMID: 22804716]
  • S Yamagata, K Tomita, H Sano, Y Itoh, Y Fukai, N Okimoto, N Watatani, S Inbe, H Miyajima, K Tsukamoto, H Santoh, H Ichihashi, A Sano, R Sato, Y Tohda. Non-genomic inhibitory effect of glucocorticoids on activated peripheral blood basophils through suppression of lipid raft formation. Clinical and experimental immunology. 2012 Oct; 170(1):86-93. doi: 10.1111/j.1365-2249.2012.04636.x. [PMID: 22943204]
  • Y C Oh, O H Kang, S B Kim, S H Mun, C B Park, Y G Kim, Y I Kim, Y S Lee, S H Han, J H Keum, D W Shin, J Y Ma, D Y Kwon. Anti-inflammatory effect of sinomenine by inhibition of pro-inflammatory mediators in PMA plus A23187-stimulated HMC-1 Cells. European review for medical and pharmacological sciences. 2012 Sep; 16(9):1184-91. doi: . [PMID: 23047501]
  • Youngjoo Sohn, Hyun-Sam Lee, Hi-Joon Park, Hyangsook Lee, Hyejung Lee, Hyeon Choi, Chang-Hyun Jeong, Youngmin Bu, Hyuk-Sang Jung. Angelicae Gigantis Radix regulates mast cell-mediated allergic inflammation in vivo and in vitro. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Sep; 50(9):2987-95. doi: 10.1016/j.fct.2012.06.001. [PMID: 22705330]
  • Piseth Khiev, Jae Wha Kim, Song Jae Sung, Hyuk-Hwan Song, Dong-Ho Choung, Young-Won Chin, Hyeong-Kyu Lee, Sei-Ryang Oh. Ingenane-type diterpenes with a modulatory effect on IFN-γ production from the roots of Euphorbia kansui. Archives of pharmacal research. 2012 Sep; 35(9):1553-8. doi: 10.1007/s12272-012-0905-1. [PMID: 23054711]
  • Liza Araújo Aguiar, Romulo Sousa Porto, Saad Lahlou, Vânia Marilande Ceccatto, Roseli Barbosa, Telma Leda Gomes Lemos, Hélcio Silva dos Santos, Andrelina Noronha Coelho-de-Souza, Pedro Jorge Caldas Magalhães, Walter Araújo Zin, José Henrique Leal-Cardoso. Antispasmodic effects of a new kaurene diterpene isolated from Croton argyrophylloides on rat airway smooth muscle. The Journal of pharmacy and pharmacology. 2012 Aug; 64(8):1155-64. doi: 10.1111/j.2042-7158.2012.01494.x. [PMID: 22775219]
  • Tamás Géczy, Attila Oláh, Balázs I Tóth, Gabriella Czifra, Attila G Szöllősi, Tamás Szabó, Christos C Zouboulis, Ralf Paus, Tamás Bíró. Protein kinase C isoforms have differential roles in the regulation of human sebocyte biology. The Journal of investigative dermatology. 2012 Aug; 132(8):1988-97. doi: 10.1038/jid.2012.94. [PMID: 22475757]
  • Ryan Dickerson, Bhakthi Deshpande, Urmila Gnyawali, Debbie Lynch, Gayle M Gordillo, Dara Schuster, Kwame Osei, Sashwati Roy. Correction of aberrant NADPH oxidase activity in blood-derived mononuclear cells from type II diabetes mellitus patients by a naturally fermented papaya preparation. Antioxidants & redox signaling. 2012 Aug; 17(3):485-91. doi: 10.1089/ars.2011.4292. [PMID: 22369197]
  • Sa-Rang Oh, Jae-Young Um, Hyong-Jun Choi, Chae-Kwang Im, Kwang-Joong Kim, Ji-Wook Jung, Gil-Saeng Jeong, Seung-Heon Hong, Su-Jin Kim. Betula platyphylla attenuated mast cell-mediated allergic inflammation in vivo and in vitro. Life sciences. 2012 Jul; 91(1-2):20-8. doi: 10.1016/j.lfs.2012.05.018. [PMID: 22683427]
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