3',4'-Dihydroxyacetophenone (BioDeep_00000008247)

Main id: BioDeep_00000396355

 

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


1-(3,4-Dihydroxyphenyl)ethanone, 9CI

化学式: C8H8O3 (152.0473)
中文名称: 3,4-二羟基苯乙酮, 3'，4'-二羟基苯乙酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1cc(c(cc1C(=O)C)O)O
InChI: InChI=1S/C8H8O3/c1-5(9)6-2-3-7(10)8(11)4-6/h2-4,10-11H,1H3

描述信息

3,4-Dihydroxyacetophenone is found in coffee and coffee products. 3,4-Dihydroxyacetophenone is extracted from coffee residues. Potential component of FEMA 3662. 3,4-Dihydroxyacetophenone is a mixture of dihydroxyacetophenone isomers is used in food flavourin
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
3',4'-Dihydroxyacetophenone (3,4-DHAP), isolated from Picea Schrenkiana Needles exhibits a strong suppressive action against tyrosinase activity, with an IC50 of 10 μM. 3',4'-Dihydroxyacetophenone (3,4-DHAP) is a vasoactive agent and antioxidant[1][2].
3',4'-Dihydroxyacetophenone (3,4-DHAP), isolated from Picea Schrenkiana Needles exhibits a strong suppressive action against tyrosinase activity, with an IC50 of 10 μM. 3',4'-Dihydroxyacetophenone (3,4-DHAP) is a vasoactive agent and antioxidant[1][2].

同义名列表

20 个代谢物同义名

1-(3,4-Dihydroxyphenyl)ethanone, 9CI; 1-(3,4-dihydroxyphenyl)ethan-1-one; 1-(3,4-Dihydroxyphenyl)-Ethanone; 1-(3,4-Dihydroxyphenyl)ethanone; 3’,4’-Dihydroxyacetophenone; Acetophenone-3,4-dihydroxy; 3,4-Dihydroxyacetophenone; 3,4-dihydroxyacetophenone; 4-ACETYL-1,2-BENZENEDIOL; 4-Acetylpyrocatechol; 4-Acetopyrocatechol; Acetylpyrocatechol; Acetopyrocatechol; 4-acetylcatechol; 4-Acetocatechol; qingxintong; 3,4-DHAP; 3',4'-Dihydroxyacetophenone; 3',4'-Dihydroxyacetophenone; 3',4'-Dihydroxyacetophenone



数据库引用编号

19 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)

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PharmGKB(0)

32 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 CDK2, HDAC2, HDAC3, MAP1A, NFKB1, NOS3, PTGS1, PTGS2, SRARP, TYR
Peripheral membrane protein 2 PTGS1, PTGS2
Endoplasmic reticulum membrane 3 HMOX1, PTGS1, PTGS2
Nucleus 9 CDK2, GABPA, HDAC2, HDAC3, HMOX1, NFKB1, NOS3, PCNA, SRARP
autophagosome 1 MAP1LC3A
cytosol 8 CDK2, GPT, HDAC3, HMOX1, MAP1A, MAP1LC3A, NFKB1, NOS3
dendrite 1 MAP1A
nuclear body 1 PCNA
centrosome 2 CDK2, PCNA
nucleoplasm 9 ATP2B1, CDK2, GABPA, HDAC2, HDAC3, HMOX1, NFKB1, NOS3, PCNA
Cell membrane 3 ATP2B1, TNF, VCAM1
Lipid-anchor 1 MAP1LC3A
Cytoplasmic side 1 HMOX1
Multi-pass membrane protein 1 ATP2B1
Synapse 2 ATP2B1, MAP1A
cell surface 3 ADIPOQ, TNF, VCAM1
dendritic shaft 1 MAP1A
glutamatergic synapse 2 ATP2B1, MAP1LC3A
Golgi apparatus 4 HDAC3, NOS3, PTGS1, VCAM1
Golgi membrane 1 NOS3
neuronal cell body 2 MAP1A, TNF
presynaptic membrane 1 ATP2B1
sarcolemma 1 VCAM1
Cytoplasm, cytosol 1 HDAC3
Lysosome 1 TYR
endosome 1 CDK2
plasma membrane 5 ATP2B1, HDAC3, NOS3, TNF, VCAM1
synaptic vesicle membrane 1 ATP2B1
Membrane 4 ATP2B1, HDAC2, HMOX1, VCAM1
axon 1 MAP1A
basolateral plasma membrane 1 ATP2B1
caveola 2 NOS3, PTGS2
extracellular exosome 5 ATP2B1, GPT, PCNA, PTGS1, VCAM1
endoplasmic reticulum 4 ADIPOQ, HMOX1, PTGS2, VCAM1
extracellular space 5 ADIPOQ, HMOX1, IL10, TNF, VCAM1
perinuclear region of cytoplasm 3 HMOX1, NOS3, TYR
mitochondrion 1 NFKB1
protein-containing complex 2 HDAC2, PTGS2
intracellular membrane-bounded organelle 4 ATP2B1, MAP1LC3A, PTGS1, TYR
Microsome membrane 2 PTGS1, PTGS2
filopodium 1 VCAM1
ESC/E(Z) complex 1 HDAC2
Single-pass type I membrane protein 2 TYR, VCAM1
Secreted 2 ADIPOQ, IL10
extracellular region 4 ADIPOQ, IL10, NFKB1, TNF
mitochondrial outer membrane 1 HMOX1
transcription regulator complex 2 CDK2, NFKB1
photoreceptor outer segment 1 PTGS1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CDK2
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 2 TNF, VCAM1
axon cytoplasm 1 MAP1A
Melanosome membrane 1 TYR
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Early endosome 1 VCAM1
apical part of cell 1 VCAM1
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 2 MAP1A, MAP1LC3A
microtubule 2 MAP1A, MAP1LC3A
collagen trimer 1 ADIPOQ
collagen-containing extracellular matrix 1 ADIPOQ
lateral plasma membrane 1 ATP2B1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 MAP1LC3A
neuron projection 3 MAP1A, PTGS1, PTGS2
chromatin 5 GABPA, HDAC2, HDAC3, NFKB1, PCNA
microtubule associated complex 1 MAP1A
Cytoplasmic vesicle, autophagosome membrane 1 MAP1LC3A
autophagosome membrane 1 MAP1LC3A
cell projection 1 ATP2B1
phagocytic cup 1 TNF
mitotic spindle 1 HDAC3
Chromosome 1 HDAC3
cytoskeleton 1 NOS3
podosome 1 VCAM1
nuclear replication fork 1 PCNA
chromosome, telomeric region 3 CDK2, HDAC2, PCNA
Basolateral cell membrane 1 ATP2B1
organelle membrane 1 MAP1LC3A
nuclear envelope 1 CDK2
Endomembrane system 2 MAP1LC3A, PTGS1
microvillus 1 VCAM1
axon initial segment 1 MAP1A
Melanosome 1 TYR
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
Presynaptic cell membrane 1 ATP2B1
replication fork 1 PCNA
secretory granule lumen 1 NFKB1
endoplasmic reticulum lumen 1 PTGS2
transcription repressor complex 1 HDAC3
male germ cell nucleus 2 CDK2, PCNA
specific granule lumen 1 NFKB1
endocytic vesicle membrane 1 NOS3
histone deacetylase complex 2 HDAC2, HDAC3
NuRD complex 1 HDAC2
immunological synapse 1 ATP2B1
Single-pass type IV membrane protein 1 HMOX1
nuclear lamina 1 PCNA
Cajal body 1 CDK2
Sin3-type complex 1 HDAC2
condensed chromosome 1 CDK2
Nucleus, Cajal body 1 CDK2
X chromosome 1 CDK2
Y chromosome 1 CDK2
cyclin-dependent protein kinase holoenzyme complex 2 CDK2, PCNA
dendritic microtubule 1 MAP1A
cyclin E1-CDK2 complex 1 CDK2
cyclin E2-CDK2 complex 1 CDK2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
Autolysosome 1 MAP1LC3A
dendritic branch 1 MAP1A
primary dendrite 1 MAP1A
photoreceptor ribbon synapse 1 ATP2B1
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
[Vascular cell adhesion protein 1]: Cell membrane 1 VCAM1
[Soluble Vascular Cell Adhesion Molecule-1]: Secreted 1 VCAM1
alpha9-beta1 integrin-vascular cell adhesion molecule-1 complex 1 VCAM1
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
cyclin A2-CDK2 complex 1 CDK2
cyclin A1-CDK2 complex 1 CDK2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Zongguang Hui, Xuewei Zhou, Rujiang Li. Effect of 3,4-dihydroxyacetophenone on endothelial dysfunction in obese rats. Pharmaceutical biology. 2015 Aug; 53(8):1149-54. doi: 10.3109/13880209.2014.962060. [PMID: 25693637]
  • Caiyan Liu, Jie Sun, Feng Xue, Yanchun Yi, Aiqiang Han. Effect of 3,4-dihydroxyacetophenone on endothelial dysfunction in streptozotocin-induced rats with type 2 diabetes. Journal of cardiovascular pharmacology. 2015 Jan; 65(1):22-7. doi: 10.1097/fjc.0000000000000158. [PMID: 25162436]
  • Daijuan Zhang, Jiangyue Liu, Lin Wang, Jianying Wang, Wentao Li, Baoxiang Zhuang, Jianping Hou, Tongmei Liu. Effects of 3,4-dihydroxyacetophenone on the hypercholesterolemia-induced atherosclerotic rabbits. Biological & pharmaceutical bulletin. 2013; 36(5):733-40. doi: 10.1248/bpb.b12-00710. [PMID: 23412669]
  • Xiao Ruan, Zhao-Hui Li, Qiang Wang, Cun-De Pan, De-An Jiang, G Geoff Wang. Autotoxicity and allelopathy of 3,4-dihydroxyacetophenone isolated from Picea schrenkiana needles. Molecules (Basel, Switzerland). 2011 Oct; 16(10):8874-93. doi: 10.3390/molecules16108874. [PMID: 22024957]
  • Liya Li, Navindra P Seeram. Further investigation into maple syrup yields 3 new lignans, a new phenylpropanoid, and 26 other phytochemicals. Journal of agricultural and food chemistry. 2011 Jul; 59(14):7708-16. doi: 10.1021/jf2011613. [PMID: 21675726]
  • Yi-Bin Zhao, Yue-Mao Shen, Hong-Ping He, Quan-Zhang Mu, Xiao-Jiang Hao. Antifungal agent and other constituents from Cynanchum otophyllum. Natural product research. 2007 Mar; 21(3):203-10. doi: 10.1080/14786410601130364. [PMID: 17365709]
  • Xue-ya Lu, Wei-chang Chen. Effect of 3, 4-dihydroxyacetophenone on Na+, K+ -ATPase activity of injured mitochondria and the oxygen consumption of brain cells of rat. Yao xue xue bao = Acta pharmaceutica Sinica. 2005 Jan; 40(1):13-6. doi: . [PMID: 15881319]
  • Shizuka Saito, Jun Kawabata. Synergistic effects of thiols and amines on antiradical efficiency of protocatechuic acid. Journal of agricultural and food chemistry. 2004 Dec; 52(26):8163-8. doi: 10.1021/jf048970j. [PMID: 15612812]
  • S H Day, J P Wang, S J Won, C N Lin. Bioactive constituents of the roots of Cynanchum atratum. Journal of natural products. 2001 May; 64(5):608-11. doi: 10.1021/np000428b. [PMID: 11374953]
  • Y Huang, D Ye, T Ma. [The effects of 3,4-dihydroxyacetophynone on the activity of nitric oxide synthetase in placental vascular endothelial cells and smooth muscle cells and on the level of endothelin-1 in plasma from pregnancy-induced hypertension patients]. Zhonghua fu chan ke za zhi. 1996 Nov; 31(11):667-9. doi: . [PMID: 9387527]
  • F Qiao, L Wen, J Xu. [Uteroplacental blood flow monitoring by color Doppler flow imaging in pregnancy induced hypertension]. Zhonghua fu chan ke za zhi. 1995 Jun; 30(6):337-9. doi: . [PMID: 7555365]
  • C Lin, Z Zhang, Y Xu. [Therapeutical mechanism of 3,4 dihydroxyacetophenone in treating chronic obstructive pulmonary disease]. Zhonghua jie he he hu xi za zhi = Zhonghua jiehe he huxi zazhi = Chinese journal of tuberculosis and respiratory diseases. 1995 Apr; 18(2):97-8, 128. doi: . [PMID: 7553961]
  • C L Lin, Z X Zhang, Y J Xu. [Effects of dihydroxyacetophenone on pulmonary hemodynamics and plasma ANP as well as cAMP/cGMP level in patients with chronic obstructive pulmonary disease]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 1995 Mar; 15(3):131-3. doi: NULL. [PMID: 7647523]
  • D H Peng, L Shi. [Effect of 3,4-dihydroxyacetophenone on phospholipid components of platelet membrane in aged rats]. Yao xue xue bao = Acta pharmaceutica Sinica. 1995; 30(5):343-6. doi: ". [PMID: 7660804]
  • Y P Sun. [Effect of 3,4-dihydroxyacetophenone on platelet aggregation in normal pregnancy and pregnancy induced hypertension]. Zhonghua fu chan ke za zhi. 1992 Jan; 27(1):9-11, 57. doi: . [PMID: 1505279]
  • D S Yang, W Xi-rui, M Ting-yuan. Effects of 3,4-dihydroxyacetophenone on the biosynthesis of TXA2 and PGI2 in human placental villus and umbilical artery segments in vitro. Prostaglandins. 1989 Oct; 38(4):497-504. doi: 10.1016/0090-6980(89)90131-7. [PMID: 2510216]
  • Q B Zhang, K R Gu. [Dihydroxyacetophenone and dihydroxyphenyllactic acid increased blood flow in rat liver microcirculation]. Zhong xi yi jie he za zhi = Chinese journal of modern developments in traditional medicine. 1987 Oct; 7(10):608-9, 582. doi: ". [PMID: 3447762]
  • Y Z Liu. [Effect of Qingxintong on exercise ECG and cardiac function in patients with angina pectoris]. Zhong xi yi jie he za zhi = Chinese journal of modern developments in traditional medicine. 1984 May; 4(5):262-4. doi: . [PMID: 6236891]