Show more...
Record Information
Version2.0
Created at2022-09-02 15:15:03 UTC
Updated at2022-09-02 15:15:03 UTC
NP-MRD IDNP0157783
Secondary Accession NumbersNone
Natural Product Identification
Common Namespiramycin ii
DescriptionSpiramycin II, also known as foromacidin b or acetylspiramycin, belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. Thus, spiramycin II is considered to be an ansamycin. Spiramycin II is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. spiramycin ii was first documented in 1990 (PMID: 2232146). Based on a literature review a significant number of articles have been published on spiramycin II (PMID: 28278108) (PMID: 20490499) (PMID: 19306580) (PMID: 15127585) (PMID: 16496680) (PMID: 20843520).
Structure
Thumb
Synonyms
ValueSource
AcetylspiramycinChEBI
AcetylspiramycinumChEBI
Foromacidin bChEBI
Foromacidine bChEBI
Spiramycin 2ChEBI
Spiramycin bChEBI
Chemical FormulaC45H76N2O15
Average Mass885.1020 Da
Monoisotopic Mass884.52457 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CO[C@H]1[C@@H](CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O[C@H]2CC[C@@H]([C@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](O)[C@H](C)O2)[C@@H]([C@H]1O)N(C)C)OC(C)=O
InChI Identifier
InChI=1S/C45H76N2O15/c1-25-22-31(20-21-48)41(62-44-39(51)38(47(10)11)40(28(4)58-44)61-37-24-45(7,53)43(52)29(5)57-37)42(54-12)34(59-30(6)49)23-35(50)55-26(2)16-14-13-15-17-33(25)60-36-19-18-32(46(8)9)27(3)56-36/h13-15,17,21,25-29,31-34,36-44,51-53H,16,18-20,22-24H2,1-12H3/b14-13+,17-15+/t25-,26-,27+,28-,29+,31+,32+,33+,34-,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1
InChI KeyZPCCSZFPOXBNDL-RSMXASMKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Dicarboxylic acid or derivatives
  • Oxane
  • Alpha-hydrogen aldehyde
  • Tertiary alcohol
  • Carboxylic acid ester
  • 1,2-aminoalcohol
  • Lactone
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Dialkyl ether
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Ether
  • Acetal
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Aldehyde
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.51ALOGPS
logS-4ALOGPS
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445368
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282173
PDB IDNot Available
ChEBI ID31168
Good Scents IDNot Available
References
General References
  1. Li Z, Hu F, Ye R, Lv H, Zeng J: Influence of Al(3+) on the titer of spiramycin and effective components in fermentor. Prep Biochem Biotechnol. 2017 May 28;47(5):481-488. doi: 10.1080/10826068.2017.1292290. Epub 2017 Feb 17. [PubMed:28278108 ]
  2. Ma C, Zhou H, Li J, Dai J, He W, Wang H, Wu L, Wang Y: Construction of 4"-isovalerylspiramycin-I-producing strain by in-frame partial deletion of 3-O-acyltransferase gene in Streptomyces spiramyceticus WSJ-1, the bitespiramycin producer. Curr Microbiol. 2011 Jan;62(1):16-20. doi: 10.1007/s00284-010-9664-8. Epub 2010 May 19. [PubMed:20490499 ]
  3. Ma C, Wu L, Dai J, Zhou H, Li J, Sun X, Zhang K, Xia H, Wang Y: [Acylation specificity of midecamycin 3-O-acyltransferase within Streptomyces spiramyceticus F21]. Sheng Wu Gong Cheng Xue Bao. 2008 Dec;24(12):2086-92. [PubMed:19306580 ]
  4. Luan XJ, Song ZH, Xiao Z: Monitoring sub-nanogram amount of acetylspiramycin in human urine using flow injection analysis with chemiluminescence detection. Yao Xue Xue Bao. 2004 Jan;39(1):64-7. [PubMed:15127585 ]
  5. Wang FM: [Parallel catalytic hydrogen wave of acetylspiramycin caused by dissolved oxygen and its application]. Yao Xue Xue Bao. 2005 Dec;40(12):1135-8. [PubMed:16496680 ]
  6. Wang MJ, Pendela M, Hu CQ, Jin SH, Hoogmartens J, Van Schepdael A, Adams E: Impurity profiling of acetylspiramycin by liquid chromatography-ion trap mass spectrometry. J Chromatogr A. 2010 Oct 15;1217(42):6531-44. doi: 10.1016/j.chroma.2010.08.061. Epub 2010 Sep 16. [PubMed:20843520 ]
  7. Kondo A, Nakatani T, Kuzuya Y, Suzuki H, Sano H, Yamaguchi K, Shirahata K, Takahashi K, Kita K, Nishiie Y, et al.: [Studies on acetylspiramycin. 1. Separation and chemical structures of acetylspiramycin components]. Jpn J Antibiot. 1990 Jun;43(6):1152-63. [PubMed:2232146 ]
  8. Yang AM, Song JH, Huang R, Jin SJ, Yang P: [Mycoplasma pneumoniae infection and drug resistance in children: an analysis of 1026 cases]. Zhongguo Dang Dai Er Ke Za Zhi. 2013 Jul;15(7):522-5. [PubMed:23866271 ]
  9. Arai H, Sakai T, Okano K, Aoyagi R, Imai A, Takase H, Mochizuki M, Tsuneoka H: Presumed toxoplasmic central retinal artery occlusion and multifocal retinitis with perivascular sheathing. Clin Ophthalmol. 2014 Apr 23;8:789-92. doi: 10.2147/OPTH.S58669. eCollection 2014. [PubMed:24790408 ]
  10. Wang QY, Li RH, Zheng LQ, Shang XH: Prevalence and antimicrobial susceptibility of Ureaplasma urealyticum and Mycoplasma hominis in female outpatients, 2009-2013. J Microbiol Immunol Infect. 2016 Jun;49(3):359-62. doi: 10.1016/j.jmii.2014.06.007. Epub 2014 Jul 28. [PubMed:25081985 ]
  11. LOTUS database [Link]