spectinomycin (CHEBI:9215)

ChEBI > Main

CHEBI:9215 - spectinomycin

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	spectinomycin

ChEBI ID	CHEBI:9215

Definition	A pyranobenzodioxin and antibiotic that is active against gram-negative bacteria and used (as its dihydrochloride pentahydrate) to treat gonorrhea. It is produced by the bacterium Streptomyces spectabilis.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45551

Supplier Information	ChemicalBook:CB8197632, eMolecules:30151837, eMolecules:1934872, eMolecules:30157345, ZINC000053006806

Download	Molfile XML SDF

more structures >>

call loadScript javascripts\jsmol\core\package.js

call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode

call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js

Jmol JavaScript applet jmolApplet0_object__5746637489802624__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__5746637489802624__)

call loadScript javascripts\jsmol\core\corestate.z.js

viewerOptions:

{ "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45551","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__5746637489802624__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"5746637489802624","bgcolor":"#000" }

Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $

java.vendor: j2s

java.version: 0.0

os.name: j2s

Access: ALL

memory: 0.0/0.0

processors available: 1

useCommandThread: false

appletId:jmolApplet0_object (signed)

starting HoverWatcher_1

getValue emulate = null

defaults = "Jmol"

getValue boxbgcolor = null

getValue bgcolor = #000

backgroundColor = "#000"

getValue ANIMFRAMECallback = null

getValue APPLETREADYCallback = Jmol._readyCallback

APPLETREADYCallback = "Jmol._readyCallback"

getValue ATOMMOVEDCallback = null

getValue CLICKCallback = null

getValue ECHOCallback = null

getValue ERRORCallback = null

getValue EVALCallback = null

getValue HOVERCallback = null

getValue LOADSTRUCTCallback = null

getValue MEASURECallback = null

getValue MESSAGECallback = null

getValue MINIMIZATIONCallback = null

getValue PICKCallback = null

getValue RESIZECallback = null

getValue SCRIPTCallback = null

getValue SYNCCallback = null

getValue STRUCTUREMODIFIEDCallback = null

getValue doTranslate = null

language=en_US

getValue popupMenu = null

getValue script = null

Jmol applet jmolApplet0_object__5746637489802624__ ready

call loadScript javascripts\jsmol\core\corescript.z.js

call loadScript javascripts\jsmol\J\script\FileLoadThread.js

starting QueueThread0_2

script 1 started

starting HoverWatcher_3

starting HoverWatcher_4

The Resolver thinks Mol

Mrv0541 02121412103D

starting HoverWatcher_5

Time for openFile(

Mrv0541 02121412103D

47 49 0 0 0 0 999 V2000

2.0900 1.4770 -0.6070 O 0 0 0 0 0 0 0 0 0 0 0 0

3.4820 1.3000 -0.8620 C 0 0 2 0 0 0 0 0 0 0 0 0

3.8560 2.0080 -2.1650 C 0 0 0 0 0 0 0 0 0 0 0 0

3.8010 -0.1950 -0.9860 C 0 0 1 0 0 0 0 0 0 0 0 0

3.3150 -0.9060 0.2900 C 0 0 0 0 0 0 0 0 0 0 0 0

4.0020 -1.7150 0.8660 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9280 -0.5070 0.7670 C 0 0 1 0 0 0 0 0 0 0 0 0

1.7090 -0.9750 2.1000 O 0 0 0 0 0 0 0 0 0 0 0 0

1.8260 1.0210 0.7160 C 0 0 2 0 0 0 0 0 0 0 0 0

0.9670 -1.0770 -0.1220 O 0 0 0 0 0 0 0 0 0 0 0 0

0.5310 1.4390 1.1310 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.3250 -0.6430 0.3070 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.3840 -1.2640 -0.6080 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.3090 -2.7290 -0.5160 N 0 0 1 0 0 0 0 0 0 0 0 0

-1.8480 -3.2590 -1.7750 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.7760 -0.7990 -0.1780 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.0180 -1.1980 1.1730 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.8520 0.7270 -0.2810 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.1910 1.1790 0.1210 N 0 0 2 0 0 0 0 0 0 0 0 0

-5.0560 1.0360 -1.0570 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8040 1.3480 0.6430 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.8670 2.7740 0.5780 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.4100 0.8820 0.2300 C 0 0 1 0 0 0 0 0 0 0 0 0

4.0580 1.7260 -0.0400 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6350 3.0720 -2.0770 H 0 0 0 0 0 0 0 0 0 0 0 0

4.9190 1.8730 -2.3610 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2780 1.5840 -2.9870 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2880 -0.6100 -1.8540 H 0 0 0 0 0 0 0 0 0 0 0 0

4.8770 -0.3350 -1.0920 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8000 -1.9370 2.0770 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5680 1.4470 1.3910 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4960 -0.9660 1.3340 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2010 -0.9560 -1.6370 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3290 -2.9680 -0.4970 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8810 -2.9310 -1.8950 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2510 -2.8920 -2.6100 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8140 -4.3480 -1.7550 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5270 -1.2450 -0.8300 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.9020 -0.8830 1.4030 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6580 1.0320 -1.3090 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1180 2.1680 0.3090 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.7110 1.7050 -1.8450 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.0190 0.0060 -1.4120 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.0810 1.2900 -0.7880 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0080 1.0220 1.6630 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7230 3.0330 0.9450 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2010 1.2360 -0.7800 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 9 1 0 0 0 0

2 3 1 0 0 0 0

2 4 1 0 0 0 0

2 24 1 0 0 0 0

3 25 1 0 0 0 0

3 26 1 0 0 0 0

3 27 1 0 0 0 0

4 5 1 0 0 0 0

4 28 1 0 0 0 0

4 29 1 0 0 0 0

5 6 2 0 0 0 0

5 7 1 0 0 0 0

7 8 1 0 0 0 0

7 9 1 0 0 0 0

7 10 1 0 0 0 0

8 30 1 0 0 0 0

9 11 1 0 0 0 0

9 31 1 0 0 0 0

10 12 1 0 0 0 0

11 23 1 0 0 0 0

12 13 1 0 0 0 0

12 23 1 0 0 0 0

12 32 1 0 0 0 0

13 14 1 0 0 0 0

13 16 1 0 0 0 0

13 33 1 0 0 0 0

14 15 1 0 0 0 0

14 34 1 0 0 0 0

15 35 1 0 0 0 0

15 36 1 0 0 0 0

15 37 1 0 0 0 0

16 17 1 0 0 0 0

16 18 1 0 0 0 0

16 38 1 0 0 0 0

17 39 1 0 0 0 0

18 19 1 0 0 0 0

18 21 1 0 0 0 0

18 40 1 0 0 0 0

19 20 1 0 0 0 0

19 41 1 0 0 0 0

20 42 1 0 0 0 0

20 43 1 0 0 0 0

20 44 1 0 0 0 0

21 22 1 0 0 0 0

21 23 1 0 0 0 0

21 45 1 0 0 0 0

22 46 1 0 0 0 0

23 47 1 0 0 0 0

M END): 22 ms

reading 47 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

47 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Spectinomycin, sold under the tradename Trobicin among others, is an antibiotic useful for the treatment of gonorrhea infections. It is given by injection into a muscle. Common side effects include pain at the area of injection, rash, nausea, fever, and trouble sleeping. Severe allergic reactions may occasionally occur. It is generally safe to use during pregnancy. It may be used by those who are allergic to penicillin or cephalosporins. It is in the aminocyclitol class of drugs and works by stopping the making of protein by certain bacteria. Spectinomycin was discovered in 1961. It is on the World Health Organization's List of Essential Medicines. It is not available in the United States for human use. It is made from the bacterium Streptomyces spectabilis.
Read full article at Wikipedia

Formula

C14H24N2O7

Net Charge

Average Mass

332.34960

Monoisotopic Mass

332.15835

InChI

InChI=1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1

InChIKey

UNFWWIHTNXNPBV-WXKVUWSESA-N

SMILES

CN[C@@H]1[C@H](O)[C@H](NC)[C@H]2O[C@]3(O)[C@@H](O[C@H](C)CC3=O)O[C@@H]2[C@H]1O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. antibacterial drug A drug used to treat or prevent bacterial infections.

Application(s):	antibacterial drug A drug used to treat or prevent bacterial infections.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	spectinomycin (CHEBI:9215) has role antibacterial drug (CHEBI:36047) spectinomycin (CHEBI:9215) has role antimicrobial agent (CHEBI:33281) spectinomycin (CHEBI:9215) has role bacterial metabolite (CHEBI:76969) spectinomycin (CHEBI:9215) is a cyclic acetal (CHEBI:59770) spectinomycin (CHEBI:9215) is a cyclic hemiketal (CHEBI:59780) spectinomycin (CHEBI:9215) is a cyclic ketone (CHEBI:3992) spectinomycin (CHEBI:9215) is a pyranobenzodioxin (CHEBI:146295) spectinomycin (CHEBI:9215) is a secondary alcohol (CHEBI:35681) spectinomycin (CHEBI:9215) is a secondary amino compound (CHEBI:50995) spectinomycin (CHEBI:9215) is conjugate base of spectinomycin(1+) (CHEBI:146260) spectinomycin (CHEBI:9215) is conjugate base of spectinomycin(2+) (CHEBI:77315)

Incoming	spectinomycin(1+) (CHEBI:146260) is conjugate acid of spectinomycin (CHEBI:9215) spectinomycin(2+) (CHEBI:77315) is conjugate acid of spectinomycin (CHEBI:9215)

IUPAC Name

(2R,4aR,5aR,6S,7S,8R,9S,9aR,10aS)-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)decahydro-4H-pyrano[2,3-b][1,4]benzodioxin-4-one

INNs	Sources
espectinomicina	DrugBank
spectinomycin	KEGG DRUG
spectinomycine	DrugBank
spectinomycinum	DrugBank

Synonym	Source
Antibiotic 2233wp	ChemIDplus

Manual Xrefs	Databases
2468	DrugCentral
C02078	KEGG COMPOUND
D08526	KEGG DRUG
DB00919	DrugBank
HMDB0015055	HMDB
LSM-5298	LINCS
SCM	PDBeChem
Spectinomycin	Wikipedia
US4203903	Patent
WO2005041984	Patent
View more database links

Registry Numbers	Types	Sources
1695-77-8	CAS Registry Number	ChemIDplus
2171701	Reaxys Registry Number	Reaxys

Citations

Chen SC, Hu LH, Zhu XY, Yin YP (2020)
Gonococcal urethritis caused by a multidrug resistant Neisseria gonorrhoeae strain with high-level resistance to spectinomycin in China.
Emerging microbes & infections 9, 517-519 [PubMed:32116136]
[show Abstract]

Molognoni L, de Souza NC, de Sá Ploêncio LA, Micke GA, Daguer H (2018)
Simultaneous analysis of spectinomycin, halquinol, zilpaterol, and melamine in feedingstuffs by ion-pair liquid chromatography-tandem mass spectrometry.
Journal of chromatography. A 1569, 110-117 [PubMed:30033166]
[show Abstract]

Lamichhane J, Jha AK, Singh B, Pandey RP, Sohng JK (2014)
Heterologous production of spectinomycin in Streptomyces venezuelae by exploiting the dTDP-D-desosamine pathway.
Journal of biotechnology 174, 57-63 [PubMed:24503209]
[show Abstract]

Jamrozy DM, Coldham NG, Butaye P, Fielder MD (2014)
Identification of a novel plasmid-associated spectinomycin adenyltransferase gene spd in methicillin-resistant Staphylococcus aureus ST398 isolated from animal and human sources.
The Journal of antimicrobial chemotherapy 69, 1193-1196 [PubMed:24402501]
[show Abstract]

Unemo M, Golparian D, Skogen V, Olsen AO, Moi H, Syversen G, Hjelmevoll SO (2013)
Neisseria gonorrhoeae strain with high-level resistance to spectinomycin due to a novel resistance mechanism (mutated ribosomal protein S5) verified in Norway.
Antimicrobial agents and chemotherapy 57, 1057-1061 [PubMed:23183436]
[show Abstract]

Madhura DB, Lee R, Meibohm B (2013)
Pharmacokinetic profile of spectinomycin in rats.
Die Pharmazie 68, 675-676 [PubMed:24020122]
[show Abstract]

Ilina EN, Malakhova MV, Bodoev IN, Oparina NY, Filimonova AV, Govorun VM (2013)
Mutation in ribosomal protein S5 leads to spectinomycin resistance in Neisseria gonorrhoeae.
Frontiers in microbiology 4, 186 [PubMed:23847609]
[show Abstract]

Last Modified

10 March 2020

ChEBI

CHEBI:9215 - spectinomycin

Objectives

Methods

Results

Conclusions

ChEBI is part of the ELIXIR infrastructure