Phellamurin (BioDeep_00000000907)

 

Secondary id: BioDeep_00000860279

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chroman-4-one

化学式: C26H30O11 (518.1788)
中文名称: (二氢)黄柏甙, 黄柏苷
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 69.55%

分子结构信息

SMILES: c(c1C(O4)([H])C(C(c(c43)c(O)cc(c(CC=C(C)C)3)OC(C2O)OC(CO)C(O)C2O)=O)([H])O)cc(O)cc1
InChI: InChI=1S/C26H30O11/c1-11(2)3-8-14-16(35-26-23(34)21(32)19(30)17(10-27)36-26)9-15(29)18-20(31)22(33)24(37-25(14)18)12-4-6-13(28)7-5-12/h3-7,9,17,19,21-24,26-30,32-34H,8,10H2,1-2H3/t17-,19-,21+,22+,23-,24-,26-/m1/s1

描述信息

Phellamurin is a member of the class of dihydroflavonols that is (+)-dihydrokaempferol substituted by a prenyl group at position 8 and a beta-D-glucopyranosyl group at position 7 via a glycosidic linkage. Isolated from Phellodendron amurense and Commiphora africana, it exhibits inhibition of intestinal P-glycoprotein. It has a role as a metabolite. It is a member of dihydroflavonols, a flavanone glycoside, a trihydroxyflavanone, a monosaccharide derivative, a beta-D-glucoside and a member of 4-hydroxyflavanones. It is functionally related to a (+)-dihydrokaempferol.
Phellamurin is a natural product found in Commiphora africana, Phellodendron chinense, and other organisms with data available.
A member of the class of dihydroflavonols that is (+)-dihydrokaempferol substituted by a prenyl group at position 8 and a beta-D-glucopyranosyl group at position 7 via a glycosidic linkage. Isolated from Phellodendron amurense and Commiphora africana, it exhibits inhibition of intestinal P-glycoprotein.
Origin: Plant, Pyrans

同义名列表

20 个代谢物同义名

(2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chroman-4-one; (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one; 4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-, (2R,3R)-; 4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTENYL)-, (2R-TRANS)-; 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-2,3-dihydro-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-, (2R-trans)-; 4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTENYL)-, (2R,3R)-; (2R,3R)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-4H-1-BENZOPYRAN-4-ONE; 3,4,5,7-tetrahydroxy-8-isoprenylflavanone-7-O-glucoside; 8-Prenyldihydrokaempferol 7-glucoside; Fellavin; Flacoside; UNII-UXB86HY2NK; MEGxp0_002039; ACon1_000824; Phellamurin; UXB86HY2NK; fellavine; FLACOSIDE; FELLAVIN; (2R) -7- (beta-D-Glucopyranosyloxy) -2,3-dihydro-3beta,5-dihydroxy-2alpha- (4-hydroxyphenyl) -8- (3-methyl-2-butenyl) -4H-1-benzopyran-4-one; Phellamurin



数据库引用编号

26 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)

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 4 ABCB1, CAT, MTOR, PIK3CA
Peripheral membrane protein 2 ACHE, MTOR
Endoplasmic reticulum membrane 1 MTOR
Nucleus 2 ACHE, MTOR
cytosol 3 CAT, MTOR, PIK3CA
dendrite 1 MTOR
phagocytic vesicle 1 MTOR
nucleoplasm 2 ATP2B1, MTOR
Cell membrane 3 ABCB1, ACHE, ATP2B1
Cytoplasmic side 1 MTOR
lamellipodium 1 PIK3CA
Multi-pass membrane protein 2 ABCB1, ATP2B1
Golgi apparatus membrane 1 MTOR
Synapse 2 ACHE, ATP2B1
cell surface 2 ABCB1, ACHE
glutamatergic synapse 1 ATP2B1
Golgi apparatus 1 ACHE
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
neuromuscular junction 1 ACHE
presynaptic membrane 1 ATP2B1
Lysosome 1 MTOR
plasma membrane 5 ABCB1, ACHE, ATP2B1, BCHE, PIK3CA
synaptic vesicle membrane 1 ATP2B1
Membrane 5 ABCB1, ACHE, ATP2B1, CAT, MTOR
apical plasma membrane 1 ABCB1
basolateral plasma membrane 1 ATP2B1
extracellular exosome 3 ABCB1, ATP2B1, CAT
Lysosome membrane 1 MTOR
extracellular space 2 ACHE, BCHE
perinuclear region of cytoplasm 2 ACHE, PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 1 CAT
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 2 ATP2B1, CAT
Microsome membrane 1 MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 2 ACHE, BCHE
extracellular region 3 ACHE, BCHE, CAT
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 1 MTOR
mitochondrial matrix 1 CAT
Extracellular side 1 ACHE
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Apical cell membrane 1 ABCB1
focal adhesion 1 CAT
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 MTOR
PML body 1 MTOR
lateral plasma membrane 1 ATP2B1
cell projection 1 ATP2B1
blood microparticle 1 BCHE
Basolateral cell membrane 1 ATP2B1
Lipid-anchor, GPI-anchor 1 ACHE
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
Presynaptic cell membrane 1 ATP2B1
side of membrane 1 ACHE
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 BCHE
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
immunological synapse 1 ATP2B1
nuclear envelope lumen 1 BCHE
synaptic cleft 1 ACHE
external side of apical plasma membrane 1 ABCB1
Cytoplasmic vesicle, phagosome 1 MTOR
catalase complex 1 CAT
photoreceptor ribbon synapse 1 ATP2B1
[Isoform H]: Cell membrane 1 ACHE
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA


文献列表

  • Hongzhi Zhang, Huijuan Jiang, Huixiang Zhang, Juncai Liu, Xigang Hu, Lei Chen. Anti-tumor efficacy of phellamurin in osteosarcoma cells: Involvement of the PI3K/AKT/mTOR pathway. European journal of pharmacology. 2019 Sep; 858(?):172477. doi: 10.1016/j.ejphar.2019.172477. [PMID: 31228450]
  • Keiichi Honda, Hisashi Omura, Mamoru Chachin, Seiji Kawano, Takashi A Inoue. Synergistic or antagonistic modulation of oviposition response of two swallowtail butterflies, Papilio maackii and P. protenor, to Phellodendron amurense by its constitutive prenylated flavonoid, phellamurin. Journal of chemical ecology. 2011 Jun; 37(6):575-81. doi: 10.1007/s10886-011-9965-9. [PMID: 21573758]
  • Yuka Koyama, Miwako Yamamoto, Katsuyoshi Matsunami, Hideaki Otsuka, Takakazu Shinzato, Yoshio Takeda. Prenylated flavonoid glucoside and two aliphatic alcohol glycosides from the leaves of Euodia meliaefolia (Hance) Benth. Journal of natural medicines. 2011 Jan; 65(1):212-6. doi: 10.1007/s11418-010-0460-3. [PMID: 20814754]
  • Tian-Shung Wu, Meei-Yu Hsu, Ping-Chung Kuo, B Sreenivasulu, A G Damu, Chung-Ren Su, Chia-Ying Li, Hsien-Chang Chang. Constituents from the leaves of Phellodendron amurense var. wilsonii and their bioactivity. Journal of natural products. 2003 Sep; 66(9):1207-11. doi: 10.1021/np030034v. [PMID: 14510598]
  • N A Tjukavkina, S V Geodakyan, A I Khvostova, J A Kolesnik, V I Glyzin. Simple high-performance liquid chromatographic method for the determination of a new phytochemical drug, fellavine, and its metabolites in human and rat plasma and urine. Journal of chromatography. 1991 Nov; 571(1-2):312-7. doi: 10.1016/0378-4347(91)80461-k. [PMID: 1810962]
  • S Sakai. Degradation of the plant flavonoid phellamurin by Aspergillus niger. Applied and environmental microbiology. 1977 Nov; 34(5):500-5. doi: 10.1128/aem.34.5.500-505.1977. [PMID: 412468]