Cephalosporin C (BioDeep_00000004517)

 

Secondary id: BioDeep_00000416119

human metabolite natural product


代谢物信息卡片


(6R,7R)-3-[(acetyloxy)methyl]-7-{[(5R)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

化学式: C16H21N3O8S (415.1049)
中文名称: 头孢菌素 C
谱图信息: 最多检出来源 Homo sapiens(lipidsearch) 18.77%

分子结构信息

SMILES: CC(=O)OCC1=C(C(=O)O)N2C(=O)C(NC(=O)CCCC(N)C(=O)O)C2SC1
InChI: InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1

描述信息

Cephalosporin C is an antibiotic of the cephalosporin class. It was isolated from fungi of the genus Acremonium and first characterized in 1961. Although not a very active antibiotic itself, synthetic analogs of cephalosporin C, such as cefalotin, became some of the first marketed cephalosporin antibiotic drugs. (Wikipedia)
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D002511 - Cephalosporins
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D047090 - beta-Lactams
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D007769 - Lactams

同义名列表

16 个代谢物同义名

(6R,7R)-3-[(acetyloxy)methyl]-7-{[(5R)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-(acetyloxymethyl)-7-[[(5R)-5-amino-5-carboxypentanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cephalosporin C, potassium salt, (6R-(6alpha,7beta(s*)))-isomer; Cephalosporin C, monosodium salt, (6R-(6alpha,7beta))-isomer; Cephalosporin C, sodium salt, (6R-(6alpha,7beta))-isomer; 7-(5-Amino-5-carboxyvaleramido)cephalosporanic acid; 7-(5-Amino-5-carboxyvaleramido)cephalosporanate; Cephalosporin C, monosodium salt; Cephalosporin C, potassium salt; Cephalosporin C, monozinc salt; Cephalosporin C hydrochloride; Cephalosporin C, sodium salt; Cephalosporin C, zinc salt; Cephalosporin C; Cephalosporine; Cephalosporin C



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)

PathBank(0)

PharmGKB(0)

29 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 5 ALB, CAT, DAO, DHFR, MRTFA
Peripheral membrane protein 2 CYP27A1, DAO
Endoplasmic reticulum membrane 2 CD4, MOXD1
Mitochondrion membrane 1 CYP27A1
Nucleus 3 ALB, MRTFA, OMP
cytosol 8 ALB, CAT, DAO, DHFR, GPT, MRTFA, MTRR, OMP
centrosome 1 ALB
nucleoplasm 2 MRTFA, MTRR
Cell membrane 3 CD4, DAO, SLC20A2
Multi-pass membrane protein 3 ATP4A, SLC15A1, SLC20A2
Synapse 1 OMP
cell surface 1 TNR
glutamatergic synapse 2 MRTFA, TNR
Golgi apparatus 1 ALB
mitochondrial inner membrane 2 CYP27A1, FECH
neuronal cell body 1 OMP
postsynapse 1 MRTFA
Cytoplasm, cytosol 1 DAO
Presynapse 1 MRTFA
plasma membrane 7 ATP4A, CD4, DAO, IGHE, SLC15A1, SLC20A2, ST14
presynaptic active zone 1 DAO
Membrane 5 ATP4A, CAT, SLC15A1, SLC20A2, ST14
apical plasma membrane 3 ATP4A, SLC15A1, SLC20A2
axon 1 OMP
basolateral plasma membrane 1 ST14
brush border 1 SLC15A1
extracellular exosome 6 ALB, CAT, DAO, GPT, LYZ, SLC20A2
endoplasmic reticulum 1 ALB
extracellular space 9 ALB, ATP4A, CRP, DAO, IGHE, LYZ, MOXD1, ST14, TNR
Schaffer collateral - CA1 synapse 1 TNR
bicellular tight junction 1 DAO
mitochondrion 4 CAT, CYP27A1, DHFR, FECH
protein-containing complex 2 ALB, CAT
intracellular membrane-bounded organelle 1 CAT
Single-pass type I membrane protein 3 CD4, IGHE, MOXD1
Secreted 3 ALB, CRP, DAO
extracellular region 7 ALB, CAT, CRP, DAO, IGHE, LYZ, TNR
mitochondrial matrix 3 CAT, CYP27A1, FECH
Extracellular side 1 DAO
anchoring junction 1 ALB
external side of plasma membrane 2 CD4, ST14
Secreted, extracellular space, extracellular matrix 1 TNR
Early endosome 1 CD4
Single-pass type II membrane protein 1 ST14
Apical cell membrane 3 ATP4A, SLC15A1, SLC20A2
Mitochondrion inner membrane 2 CYP27A1, FECH
Membrane raft 2 CD4, TNR
focal adhesion 1 CAT
Peroxisome 2 CAT, DAO
Peroxisome matrix 2 CAT, DAO
peroxisomal matrix 2 CAT, DAO
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 TNR
ciliary basal body 1 ALB
IgE immunoglobulin complex 1 IGHE
cell projection 1 DAO
centriole 1 ALB
Secreted, extracellular space 1 DAO
brush border membrane 1 SLC20A2
spindle pole 1 ALB
blood microparticle 1 ALB
[Isoform 2]: Cell membrane 1 IGHE
intermediate filament cytoskeleton 1 MTRR
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
secretory granule membrane 1 MOXD1
endoplasmic reticulum lumen 2 ALB, CD4
platelet alpha granule lumen 1 ALB
specific granule lumen 2 DAO, LYZ
tertiary granule lumen 1 LYZ
azurophil granule lumen 1 LYZ
perineuronal net 1 TNR
clathrin-coated endocytic vesicle membrane 1 CD4
[Isoform 3]: Cell membrane 1 IGHE
T cell receptor complex 1 CD4
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
catalase complex 1 CAT
potassium:proton exchanging ATPase complex 1 ATP4A
tenascin complex 1 TNR
ciliary transition fiber 1 ALB
[Isoform A]: Cytoplasm 1 MTRR


文献列表

  • Yan Xu, Ling Liu, Zhen Chen, Xiwei Tian, Ju Chu. The arthrospore-related gene Acaxl2 is involved in cephalosporin C production in industrial Acremonium chrysogenum by the regulatory factors AcFKH1 and CPCR1. Journal of biotechnology. 2022 Mar; 347(?):26-39. doi: 10.1016/j.jbiotec.2021.12.011. [PMID: 34954288]
  • Alexander Zhgun, Mariya Dumina, Ayrat Valiakhmetov, Mikhail Eldarov. The critical role of plasma membrane H+-ATPase activity in cephalosporin C biosynthesis of Acremonium chrysogenum. PloS one. 2020; 15(8):e0238452. doi: 10.1371/journal.pone.0238452. [PMID: 32866191]
  • Chang Chen, Jia He, Wenyan Gao, Yanmin Wei, Gang Liu. Identification and Characterization of an Autophagy-Related Gene Acatg12 in Acremonium chrysogenum. Current microbiology. 2019 May; 76(5):545-551. doi: 10.1007/s00284-019-01650-7. [PMID: 30899986]
  • Geetika Dhanda, Paramita Sarkar, Sandip Samaddar, Jayanta Haldar. Battle against Vancomycin-Resistant Bacteria: Recent Developments in Chemical Strategies. Journal of medicinal chemistry. 2019 04; 62(7):3184-3205. doi: 10.1021/acs.jmedchem.8b01093. [PMID: 30404451]
  • Juan-Francisco Martín, Carlos García-Estrada, Ricardo V Ullán. Transport of substrates into peroxisomes: the paradigm of β-lactam biosynthetic intermediates. Biomolecular concepts. 2013 Apr; 4(2):197-211. doi: 10.1515/bmc-2012-0048. [PMID: 25436576]
  • Aurijit Sarkar, Kelcey C Anderson, Glen E Kellogg. Computational analysis of structure-based interactions and ligand properties can predict efflux effects on antibiotics. European journal of medicinal chemistry. 2012 Jun; 52(?):98-110. doi: 10.1016/j.ejmech.2012.03.008. [PMID: 22483632]
  • Hyun Yong Shin, Jin Young Lee, Han Suk Choi, Ja Hyun Lee, Seung Wook Kim. Production of cephalosporin C using crude glycerol in fed-batch culture of Acremonium chrysogenum M35. Journal of microbiology (Seoul, Korea). 2011 Oct; 49(5):753-8. doi: 10.1007/s12275-011-1155-5. [PMID: 22068491]
  • A Ia Valiakhmetov, L V Trilisenko, V M Vagabov, Iu E Bartoshevich, I S Kulaev, M I Novak, A G Domracheva, M A El'darov, K G Skriabin. [The concentration dynamics of inorganic polyphosphates during the cephalosporin C synthesis by Acremonium chrysogenum]. Prikladnaia biokhimiia i mikrobiologiia. 2010 Mar; 46(2):198-204. doi: NULL. [PMID: 20391764]
  • Ivet Krastanova, Corrado Guarnaccia, Sotir Zahariev, Giuliano Degrassi, Doriano Lamba. Heterologous expression, purification, crystallization, X-ray analysis and phasing of the acetyl xylan esterase from Bacillus pumilus. Biochimica et biophysica acta. 2005 May; 1748(2):222-30. doi: 10.1016/j.bbapap.2005.01.003. [PMID: 15769599]
  • Sudha Ravishankar, Vidya Prasanna Kumar, B Chandrakala, Ramesh K Jha, Suresh M Solapure, Sunita M de Sousa. Scintillation proximity assay for inhibitors of Escherichia coli MurG and, optionally, MraY. Antimicrobial agents and chemotherapy. 2005 Apr; 49(4):1410-8. doi: 10.1128/aac.49.4.1410-1418.2005. [PMID: 15793120]
  • Loredano Pollegioni, Laura Caldinelli, Gianluca Molla, Silvia Sacchi, Mirella S Pilone. Catalytic properties of D-amino acid oxidase in cephalosporin C bioconversion: a comparison between proteins from different sources. Biotechnology progress. 2004 Mar; 20(2):467-73. doi: 10.1021/bp034206q. [PMID: 15058991]
  • Songcheng Zhu, Yunliu Yang, Guoping Zhao, Weihong Jiang. A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity. Journal of microbiological methods. 2003 Jul; 54(1):131-5. doi: 10.1016/s0167-7012(03)00013-7. [PMID: 12732432]
  • J Chen, T B Zhu, Y F Zhang, Y L Yang, R S Jiao. [Enzymatic conversion of cephalosporin C to glutaryl-7-aminocephalosporanic acid using whole cells of the yeast Trigonopsis variabilis FA10]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2001 Mar; 17(2):150-4. doi: . [PMID: 11411221]
  • N H Pham, B A Baldo. beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies. Journal of molecular recognition : JMR. 1996 Jul; 9(4):287-96. doi: 10.1002/(sici)1099-1352(199607)9:4\%3c287::aid-jmr340\%3e3.0.co;2-l. [PMID: 9131470]
  • J T Vicenzi, G J Hansen. Enzymatic oxidation of cephalosporin C using whole cells of the yeast Triginopsis variabilis within a "cross-flow filter-reactor". Enzyme and microbial technology. 1993 Apr; 15(4):281-5. doi: 10.1016/0141-0229(93)90150-z. [PMID: 7765298]
  • T Isogai, H Ono, Y Ishitani, H Kojo, Y Ueda, M Kohsaka. Structure and expression of cDNA for D-amino acid oxidase active against cephalosporin C from Fusarium solani. Journal of biochemistry. 1990 Dec; 108(6):1063-9. doi: 10.1093/oxfordjournals.jbchem.a123306. [PMID: 1982443]
  • V A Losev, B A Chagin, O N Oparina, T N Vandysheva. [Use of an aerodynamic foam quencher in the stab cultivation of mycelial fungi]. Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic]. 1988 Jun; 33(6):411-5. doi: ". [PMID: 3421764]
  • E Papacharilaou, M A Pisano. Changes in the lipid composition of Paecilomyces persicinus P-10 M1 during growth and cephalosporin C production. Applied and environmental microbiology. 1984 Dec; 48(6):1084-7. doi: 10.1128/aem.48.6.1084-1087.1984. [PMID: 6542767]
  • M H RICHMOND. WILD-TYPE VARIANTS OF EXOPENICILLINASE FROM STAPHYLOCOCCUS AUREUS. The Biochemical journal. 1965 Mar; 94(?):584-93. doi: 10.1042/bj0940584. [PMID: 14342258]
  • J M MURDOCH, C F SPEIRS, A M GEDDES, E T WALLACE. CLINICAL TRIAL OF CEPHALORIDINE (CEPORIN), A NEW BROAD-SPECTRUM ANTIBIOTIC DERIVED FROM CEPHALOSPORIN C. British medical journal. 1964 Nov; 2(5419):1238-40. doi: 10.1136/bmj.2.5419.1238. [PMID: 14205527]
  • M JAGO. ANTIBACTERIAL ACTIVITY OF SOME DERIVATIVES OF 7-AMINOCEPHALOSPORANIC ACID AGAINST STAPHYLOCOCCUS AUREUS AND SYNERGISM BETWEEN THESE AND OTHER ANTIBIOTICS. British journal of pharmacology and chemotherapy. 1964 Feb; 22(?):22-33. doi: 10.1111/j.1476-5381.1964.tb01540.x. [PMID: 14126054]
  • C W GODZESKI, G BRIER, D E PAVEY. Cephalothin, a new cephalosporin with a broad antibacterial spectrum. I. In vitro studies employing the gradient plate technique. Applied microbiology. 1963 Mar; 11(?):122-7. doi: 10.1128/am.11.2.122-127.1963. [PMID: 13963283]
  • M JAGO, N G HEATLEY. Some biological properties of cephalosporin C and a derivative. British journal of pharmacology and chemotherapy. 1961 Apr; 16(?):170-9. doi: 10.1111/j.1476-5381.1961.tb00310.x. [PMID: 13789185]