Pachypodol (BioDeep_00000007883)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-

化学式: C18H16O7 (344.0896)
中文名称: 藿香黄酮醇
谱图信息: 最多检出来源 Astragalus membranaceus(plant) 50%

分子结构信息

SMILES: c(c21)(O)cc(OC)cc(OC(c(c3)cc(OC)c(O)c3)=C(C2=O)OC)1
InChI: InChI=1S/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-11(19)13(6-9)23-2/h4-8,19-20H,1-3H3

描述信息

Pachypodol is a trimethoxyflavone that is quercetin in which the hydroxy groups at position 3, 7 and 3 are replaced by methoxy groups. It has been isolated from Combretum quadrangulare and Euodia elleryana. It has a role as a plant metabolite and an antiemetic. It is a dihydroxyflavone and a trimethoxyflavone. It is functionally related to a quercetin.
Pachypodol is a natural product found in Larrea cuneifolia, Macaranga triloba, and other organisms with data available.
A trimethoxyflavone that is quercetin in which the hydroxy groups at position 3, 7 and 3 are replaced by methoxy groups. It has been isolated from Combretum quadrangulare and Euodia elleryana.
Pachypodol exerts antioxidant and cytoprotective effects in HepG2 cells[1].Pachypodol inhibits the growth of CaCo 2 colon cancer cell line in vitro(IC50 = 185.6 mM)[2].
Pachypodol exerts antioxidant and cytoprotective effects in HepG2 cells[1].Pachypodol inhibits the growth of CaCo 2 colon cancer cell line in vitro(IC50 = 185.6 mM)[2].

同义名列表

26 个代谢物同义名

4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-; 5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4H-1-benzopyran-4-one; 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one; 5-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3,7-dimethoxy-chromen-4-one; 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxychromen-4-one; 3,7,3-quercetol trimethyl ether-5,4-dihydroxy-; 5,4-dihydroxy-3,7,3-quercetol trimethyl ether; Quercetin-3,7,3-trimethyl ether; Ro 09-0179; 5,4-dihydroxy-3,7,3-trimethoxyflavone; 4,5-dihydroxy-3,3,7-trimethoxyflavone; Quercetin 3,3,7-trimethyl ether; Quercetin 3,7,3-trimethyl ether; KQFUXLQBMQGNRT-UHFFFAOYSA-N; UNII-8AG6B2DMP5; Ro-09-0179; 8AG6B2DMP5; Ro 09-0179; Pachypodol; 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4-chromenone; 5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3,7-dimethoxy-chromone; 33708-72-4; NSC 168805; NSC168805; C10117; 5-Hydroxy-2- (4-hydroxy-3-methoxyphenyl) -3,7-dimethoxy-4H-1-benzopyran-4-one; Pachypodol



数据库引用编号

20 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)

193 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 CNP, CTSG, ELANE, ELAVL1, FPR1, MAPK8, NLRP3, OSBP, PDK1, SGCB
Peripheral membrane protein 4 AP2M1, COPB2, CTSG, OSBP
Endoplasmic reticulum membrane 2 COPB2, OSBP
Nucleus 6 CTSG, ELAVL1, GABPA, MAPK8, NLRP3, PDK1
cytosol 9 AP2M1, COPB2, CTSG, ELANE, ELAVL1, MAPK8, NLRP3, OSBP, PDK1
phagocytic vesicle 1 ELANE
trans-Golgi network 1 OSBP
nucleoplasm 4 ELAVL1, GABPA, MAPK8, OSBP
Cell membrane 5 AP2M1, CTSG, FPR1, TNF, TRPA1
Lipid-anchor 1 CNP
Cytoplasmic side 2 AP2M1, COPB2
Cytoplasmic granule 1 CTSG
Multi-pass membrane protein 2 FPR1, TRPA1
Golgi apparatus membrane 2 COPB2, NLRP3
Synapse 3 C1QA, CNP, MAPK8
cell junction 1 OSBP
cell surface 2 ELANE, TNF
glutamatergic synapse 3 AP2M1, C1QA, ELAVL1
Golgi apparatus 3 ATRN, COPB2, OSBP
Golgi membrane 3 COPB2, NLRP3, OSBP
lysosomal membrane 2 AP2M1, GAA
mitochondrial inner membrane 1 CNP
neuronal cell body 1 TNF
postsynapse 3 AP2M1, C1QA, ELAVL1
sarcolemma 1 SGCB
synaptic vesicle 1 AP2M1
Cytoplasm, cytosol 4 COPB2, CTSG, NLRP3, OSBP
Lysosome 2 CTSG, GAA
plasma membrane 11 AP2M1, ATRN, CSF2, CTSG, FPR1, GAA, OSBP, PDK1, SGCB, TNF, TRPA1
Membrane 8 CNP, CTSG, ELAVL1, FPR1, GAA, NLRP3, OSBP, TRPA1
axon 1 MAPK8
extracellular exosome 6 AP2M1, ATRN, CNP, CTSG, ELANE, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 2 ELAVL1, NLRP3
extracellular space 6 ATRN, CNP, CSF2, CTSG, ELANE, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 CNP, OSBP
mitochondrion 2 NLRP3, PDK1
intracellular membrane-bounded organelle 3 CSF2, CTSG, GAA
postsynaptic density 1 PDK1
Single-pass type I membrane protein 1 ATRN
Secreted 5 C1QA, CSF2, CTSG, GAA, NLRP3
extracellular region 7 C1QA, CSF2, CTSG, ELANE, GAA, NLRP3, TNF
cytoplasmic side of plasma membrane 1 AP2M1
mitochondrial outer membrane 1 CNP
[Isoform 2]: Secreted 1 ATRN
Mitochondrion matrix 1 PDK1
mitochondrial matrix 1 PDK1
external side of plasma membrane 1 TNF
cytoplasmic vesicle 3 AP2M1, ELAVL1, PDK1
nucleolus 1 OSBP
clathrin adaptor complex 1 AP2M1
sarcoplasm 1 ELAVL1
Cytoplasm, P-body 1 ELAVL1
P-body 1 ELAVL1
clathrin-coated pit 1 AP2M1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 SGCB, TNF
Cell membrane, sarcolemma 1 SGCB
Cytoplasm, perinuclear region 1 OSBP
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 SGCB
focal adhesion 1 PDK1
microtubule 1 CNP
collagen trimer 1 C1QA
collagen-containing extracellular matrix 3 C1QA, CTSG, ELANE
secretory granule 2 CTSG, ELANE
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
chromatin 1 GABPA
stereocilium bundle 1 TRPA1
cell projection 1 PDK1
phagocytic cup 1 TNF
cytoskeleton 1 SGCB
Golgi apparatus, trans-Golgi network 1 OSBP
[Isoform 3]: Secreted 1 ATRN
Endomembrane system 2 AP2M1, NLRP3
microvillus 1 CNP
microtubule organizing center 1 NLRP3
tertiary granule membrane 1 GAA
Melanosome 1 CNP
Cytoplasm, Stress granule 1 ELAVL1
cytoplasmic stress granule 2 CTSG, ELAVL1
pseudopodium 1 CNP
secretory granule membrane 1 FPR1
transcription repressor complex 1 ELANE
pyruvate dehydrogenase complex 1 PDK1
specific granule lumen 1 ELANE
endocytic vesicle membrane 1 AP2M1
transport vesicle 1 COPB2
azurophil granule membrane 2 FPR1, GAA
azurophil granule lumen 2 CTSG, ELANE
Cytoplasmic vesicle, COPI-coated vesicle membrane 1 COPB2
COPI vesicle coat 1 COPB2
clathrin-coated endocytic vesicle 1 AP2M1
perinuclear endoplasmic reticulum 1 OSBP
clathrin-coated endocytic vesicle membrane 1 AP2M1
ribonucleoprotein complex 1 ELAVL1
ficolin-1-rich granule membrane 2 FPR1, GAA
endolysosome membrane 1 AP2M1
basal dendrite 1 MAPK8
[Isoform 1]: Cell membrane 1 ATRN
membrane coat 1 COPB2
dystrophin-associated glycoprotein complex 1 SGCB
sarcoglycan complex 1 SGCB
COPI-coated vesicle membrane 1 COPB2
Cytoplasmic vesicle, phagosome 1 ELANE
Membrane, coated pit 1 AP2M1
extrinsic component of presynaptic endocytic zone membrane 1 AP2M1
granulocyte macrophage colony-stimulating factor receptor complex 1 CSF2
AP-2 adaptor complex 1 AP2M1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
complement component C1 complex 1 C1QA
complement component C1q complex 1 C1QA
extrinsic component of postsynaptic membrane 1 C1QA
extrinsic component of presynaptic membrane 1 C1QA
myelin sheath abaxonal region 1 CNP
myelin sheath adaxonal region 1 CNP
autolysosome lumen 1 GAA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Sehrish Fatima, Iqra Farzeen, Asma Ashraf, Bilal Aslam, Muhammad Umar Ijaz, Sumreen Hayat, Muhammad Hassan Sarfraz, Saima Zafar, Nimrah Zafar, Jeremiah Oshiomame Unuofin, Sogolo Lucky Lebelo, Saima Muzammil. A Comprehensive Review on Pharmacological Activities of Pachypodol: A Bioactive Compound of an Aromatic Medicinal Plant Pogostemon Cablin Benth. Molecules (Basel, Switzerland). 2023 Apr; 28(8):. doi: 10.3390/molecules28083469. [PMID: 37110702]
  • Jingxiong Zhang, Mingsheng Zhu, Jie Zhang. Pachypodol protects newborn rats from anaesthesia-induced apoptosis in the developing brain by regulating the JNK/ERK pathway. International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience. 2021 Nov; 81(7):633-642. doi: 10.1002/jdn.10140. [PMID: 34198359]
  • Thanika Promchai, Atchara Jaidee, Sarot Cheenpracha, Kongkiat Trisuwan, Roonglawan Rattanajak, Sumalee Kamchonwongpaisan, Surat Laphookhieo, Stephen G Pyne, Thunwadee Ritthiwigrom. Antimalarial Oxoprotoberberine Alkaloids from the Leaves of Miliusa cuneata. Journal of natural products. 2016 Apr; 79(4):978-83. doi: 10.1021/acs.jnatprod.5b01054. [PMID: 26928423]
  • Félix Morales-Flores, Karen Susana Olivares-Palomares, María Isabel Aguilar-Laurents, José Fausto Rivero-Cruz, Blas Lotina-Hennsen, Beatriz King-Díaz. Flavonoids Affect the Light Reaction of Photosynthesis in Vitro and in Vivo as Well as the Growth of Plants. Journal of agricultural and food chemistry. 2015 Sep; 63(37):8106-15. doi: 10.1021/acs.jafc.5b02842. [PMID: 26322527]
  • Minetaro Arita, Stefan Philipov, Angel S Galabov. Phosphatidylinositol 4-kinase III beta is the target of oxoglaucine and pachypodol (Ro 09-0179) for their anti-poliovirus activities, and is located at upstream of the target step of brefeldin A. Microbiology and immunology. 2015 Jun; 59(6):338-47. doi: 10.1111/1348-0421.12261. [PMID: 25891300]
  • Chun-ying Xie, Le-wei Lin. [Study on the chemical constituents of Pithecellobium clypearia]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Jul; 34(7):1060-2. doi: . [PMID: 22066399]
  • Muhammad Ali Versiani, Thushara Diyabalanage, Ranjala Ratnayake, Curtis J Henrich, Susan E Bates, James B McMahon, Kirk R Gustafson. Flavonoids from eight tropical plant species that inhibit the multidrug resistance transporter ABCG2. Journal of natural products. 2011 Feb; 74(2):262-6. doi: 10.1021/np100797y. [PMID: 21275386]
  • Guo-en Yang, Li Bao, Xiao-qi Zhang, Ying Wang, Qian Li, Wei-ku Zhang, Wen-cai Ye. [Studies on flavonoids and their antioxidant activities of Artemisia annua]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Nov; 32(11):1683-6. doi: . [PMID: 20218288]
  • Husne-Ara Ali, A K Azad Chowdhury, Abul K M Rahman, Tomasz Borkowski, Lutfun Nahar, Satyajit D Sarker. Pachypodol, a flavonol from the leaves of Calycopteris floribunda, inhibits the growth of CaCo 2 colon cancer cell line in vitro. Phytotherapy research : PTR. 2008 Dec; 22(12):1684-7. doi: 10.1002/ptr.2539. [PMID: 18570232]
  • Raquel González-Vázquez, Beatriz King Díaz, María Isabel Aguilar, Nelly Diego, Blas Lotina-Hennsen. Pachypodol from Croton ciliatoglanduliferus Ort. as water-splitting enzyme inhibitor on thylakoids. Journal of agricultural and food chemistry. 2006 Feb; 54(4):1217-21. doi: 10.1021/jf051897s. [PMID: 16478239]
  • D T Huong, D V Luong, T T P Thao, T V Sung. A new flavone and cytotoxic activity of flavonoid constituents isolated from Miliusa balansae (Annonaceae). Die Pharmazie. 2005 Aug; 60(8):627-9. doi: . [PMID: 16124409]
  • V Robin, A Irurzun, M Amoros, J Boustie, L Carrasco. Antipoliovirus flavonoids from Psiadia dentata. Antiviral chemistry & chemotherapy. 2001 Sep; 12(5):283-91. doi: 10.1177/095632020101200503. [PMID: 11900347]