doxycycline (CHEBI:50845)

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CHEBI:50845 - doxycycline

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ChEBI Name	doxycycline

ChEBI ID	CHEBI:50845

Definition	Tetracycline in which the 5β-hydrogen is replaced by a hydroxy group, while the 6α-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), and adult periodontitis.

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

Secondary ChEBI IDs	CHEBI:42135, CHEBI:4713

Supplier Information	ChemicalBook:CB1185500, eMolecules:984090, ZINC000000901157

Download	Molfile XML SDF

more structures >>

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8.4159 -2.3930 2.5633 C 0 0 0 0 0 0 0 0 0 0 0 0

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8.8166 -3.5938 1.7647 C 0 0 0 0 0 0 0 0 0 0 0 0

10.9914 -3.6000 0.8590 O 0 0 0 0 0 0 0 0 0 0 0 0

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9.2003 -3.2256 -0.5500 N 0 0 0 0 0 0 0 0 0 0 0 0

8.2997 -4.8017 2.0536 C 0 0 0 0 0 0 0 0 0 0 0 0

8.6716 -5.9278 1.3352 O 0 0 0 0 0 0 0 0 0 0 0 0

7.2640 -5.0490 3.1289 C 0 0 1 0 0 0 0 0 0 0 0 0

7.8939 -5.7275 4.2714 N 0 0 2 0 0 0 0 0 0 0 0 0

8.4575 -7.0059 3.8473 C 0 0 0 0 0 0 0 0 0 0 0 0

6.9189 -5.9198 5.3403 C 0 0 0 0 0 0 0 0 0 0 0 0

6.5246 -3.7477 3.5598 C 0 0 2 0 0 0 0 0 0 0 0 0

5.4299 -3.3534 2.5356 C 0 0 1 0 0 0 0 0 0 0 0 0

4.4688 -4.4187 2.5506 O 0 0 0 0 0 0 0 0 0 0 0 0

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4.2523 -1.2252 1.5909 C 0 0 1 0 0 0 0 0 0 0 0 0

3.4896 -2.1026 0.5837 C 0 0 0 0 0 0 0 0 0 0 0 0

3.4696 0.0242 2.0094 C 0 0 0 0 0 0 0 0 0 0 0 0

2.4843 0.5999 1.1870 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7879 1.7485 1.5738 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0695 2.3568 2.7894 C 0 0 0 0 0 0 0 0 0 0 0 0

3.0556 1.8250 3.6148 C 0 0 0 0 0 0 0 0 0 0 0 0

3.2889 2.4794 4.7890 O 0 0 0 0 0 0 0 0 0 0 0 0

3.7573 0.6718 3.2270 C 0 0 0 0 0 0 0 0 0 0 0 0

4.8260 0.1775 4.1258 C 0 0 0 0 0 0 0 0 0 0 0 0

5.1008 0.7731 5.1602 O 0 0 0 0 0 0 0 0 0 0 0 0

5.5233 -1.0760 3.7172 C 0 0 0 0 0 0 0 0 0 0 0 0

6.7895 -1.3089 4.1145 C 0 0 0 0 0 0 0 0 0 0 0 0

7.5483 -0.4193 4.8556 O 0 0 0 0 0 0 0 0 0 0 0 0

7.5120 -2.5915 3.7853 C 0 0 2 0 0 0 0 0 0 0 0 0

8.3893 -2.9371 4.8571 O 0 0 0 0 0 0 0 0 0 0 0 0

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6.9682 0.1427 5.3758 H 0 0 0 0 0 0 0 0 0 0 0 0

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8.6257 -5.7378 0.3960 H 0 0 0 0 0 0 0 0 0 0 0 0

6.5285 -5.7565 2.7295 H 0 0 0 0 0 0 0 0 0 0 0 0

9.1475 -6.8541 3.0139 H 0 0 0 0 0 0 0 0 0 0 0 0

7.6612 -7.6820 3.5268 H 0 0 0 0 0 0 0 0 0 0 0 0

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7.4314 -6.1516 6.2780 H 0 0 0 0 0 0 0 0 0 0 0 0

6.2457 -6.7453 5.0935 H 0 0 0 0 0 0 0 0 0 0 0 0

6.3258 -5.0125 5.4777 H 0 0 0 0 0 0 0 0 0 0 0 0

6.0162 -3.9792 4.5094 H 0 0 0 0 0 0 0 0 0 0 0 0

5.8501 -3.3154 1.5245 H 0 0 0 0 0 0 0 0 0 0 0 0

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3.8021 -2.2741 3.4373 H 0 0 0 0 0 0 0 0 0 0 0 0

5.1487 -0.8641 1.0669 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2444 0.1587 0.2222 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0270 2.1651 0.9207 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5311 3.2489 3.0949 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0348 -3.0324 0.3931 H 0 0 0 0 0 0 0 0 0 0 0 0

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M END): 25 ms

reading 56 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

56 atoms created

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

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Molfile expand

Wikipedia	License
Orsellinic acid, more specifically o-orsellinic acid, is a phenolic acid. It is of importance in the biochemistry of lichens, from which it can be extracted. It is a common subunit of depsides.
Read full article at Wikipedia

Formula

C22H24N2O8

Net Charge

Average Mass

444.43464

Monoisotopic Mass

444.15327

InChI

InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1

InChIKey

JBIWCJUYHHGXTC-AKNGSSGZSA-N

SMILES

[H][C@@]12[C@@H](C)c3cccc(O)c3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])[C@H]2O

Roles Classification
Biological Role(s):	antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. antibacterial drug A drug used to treat or prevent bacterial infections. immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via tetracyclines )

Application(s):	antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. antibacterial drug A drug used to treat or prevent bacterial infections. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. anti-inflammatory agent Any compound that has anti-inflammatory effects. immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	doxycycline (CHEBI:50845) has role anti-inflammatory agent (CHEBI:67079) doxycycline (CHEBI:50845) has role antibacterial drug (CHEBI:36047) doxycycline (CHEBI:50845) has role antimalarial (CHEBI:38068) doxycycline (CHEBI:50845) has role geroprotector (CHEBI:176497) doxycycline (CHEBI:50845) has role immunomodulator (CHEBI:50846) doxycycline (CHEBI:50845) is a tetracyclines (CHEBI:26895)

Incoming	doxycycline HCl (CHEBI:652992) has part doxycycline (CHEBI:50845) doxycycline monohydrate (CHEBI:60648) has part doxycycline (CHEBI:50845)

IUPAC Name

(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

INNs	Sources
doxiciclina	ChemIDplus
doxycycline	KEGG DRUG
doxycyclinum	ChemIDplus

Synonyms	Sources
(4S,4AR,5S,5AR,6R,12AS)-4-(DIMETHYLAMINO)-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE	PDBeChem
5-hydroxy-α-6-deoxytetracycline	ChemIDplus
6α-deoxy-5-oxytetracycline	ChemIDplus
Doxycyclin	ChEBI
Doxycycline	KEGG COMPOUND
doxycycline (anhydrous)	ChemIDplus

Brand Names	Sources
Jenacyclin	DrugBank
Supracyclin	DrugBank
Vibramycin	DrugBank

Manual Xrefs	Databases
10469369	ChemSpider
1840	VSDB
961	DrugCentral
C00017127	KNApSAcK
C06973	KEGG COMPOUND
CPD-19256	MetaCyc
D07876	KEGG DRUG
DB00254	DrugBank
Doxycycline	Wikipedia
DXT	PDBeChem
HMDB0014399	HMDB
LMPK07000001	LIPID MAPS
US3019260	Patent
US3200149	Patent
View more database links

Registry Numbers	Types	Sources
3041790	Reaxys Registry Number	Reaxys
564-25-0	CAS Registry Number	KEGG COMPOUND
564-25-0	CAS Registry Number	ChemIDplus

Citations	Types	Sources
11477376	PubMed citation	Europe PMC
11850258	PubMed citation	Europe PMC
11891205	PubMed citation	Europe PMC
1650428	PubMed citation	Europe PMC
16651635	PubMed citation	Europe PMC
19630297	PubMed citation	Europe PMC
23698443	PubMed citation	Europe PMC
24134630	PubMed citation	Europe PMC
34128838	PubMed citation	Europe PMC
34228348	PubMed citation	Europe PMC
34318509	PubMed citation	Europe PMC
34338231	PubMed citation	Europe PMC
34355683	PubMed citation	Europe PMC
34551605	PubMed citation	Europe PMC
34577552	PubMed citation	Europe PMC
PMC8464303	PubMed Central citation	Europe PMC
PMC8466018	PubMed Central citation	Europe PMC

Last Modified

29 September 2021

CHEBI:50845 - doxycycline

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