minocycline (CHEBI:50694)

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CHEBI:50694 - minocycline

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ChEBI Name	minocycline

ChEBI ID	CHEBI:50694

Definition	A tetracycline analogue having a dimethylamino group at position 7 and lacking the methyl and hydroxy groups at position 5.

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

Secondary ChEBI IDs	CHEBI:44053, CHEBI:6939

Supplier Information	ZINC000014879992

Download	Molfile XML SDF

more structures >>

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5.0560 0.1540 -2.5640 O 0 0 0 0 0 0 0 0 0 0 0 0

4.1590 -0.6070 -2.2530 C 0 0 0 0 0 0 0 0 0 0 0 0

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3.6320 -1.0900 0.0980 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5850 -2.0320 0.0590 O 0 0 0 0 0 0 0 0 0 0 0 0

2.9010 -0.8580 1.3870 C 0 0 1 0 0 0 0 0 0 0 0 0

3.7380 -0.0320 2.2670 N 0 0 0 0 0 0 0 0 0 0 0 0

3.0950 -0.0360 3.5880 C 0 0 0 0 0 0 0 0 0 0 0 0

5.0180 -0.7380 2.4180 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5720 -0.1600 1.1740 C 0 0 1 0 0 0 0 0 0 0 0 0

1.7200 1.0800 0.2920 C 0 0 1 0 0 0 0 0 0 0 0 0

2.5470 2.0480 0.9410 O 0 0 0 0 0 0 0 0 0 0 0 0

0.3570 1.6570 0.0090 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2890 2.9300 -0.4270 O 0 0 0 0 0 0 0 0 0 0 0 0

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0.5340 -1.0860 0.5460 C 0 0 0 0 0 0 0 0 0 0 0 0

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-5.6070 -0.6050 -0.0660 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.3750 -1.2500 -0.0810 C 0 0 0 0 0 0 0 0 0 0 0 0

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-4.9940 -3.1050 1.1340 C 0 0 0 0 0 0 0 0 0 0 0 0

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4.8290 -1.7850 2.6540 H 0 0 0 0 0 0 0 0 0 0 0 0

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2 3 1 0 0 0 0

2 4 1 0 0 0 0

3 45 1 0 0 0 0

3 46 1 0 0 0 0

4 5 1 0 0 0 0

4 7 2 0 0 0 0

5 6 2 0 0 0 0

5 14 1 0 0 0 0

7 8 1 0 0 0 0

7 9 1 0 0 0 0

8 47 1 0 0 0 0

9 10 1 0 0 0 0

9 13 1 0 0 0 0

9 48 1 0 0 0 0

10 11 1 0 0 0 0

10 12 1 0 0 0 0

11 49 1 0 0 0 0

11 50 1 0 0 0 0

11 51 1 0 0 0 0

12 52 1 0 0 0 0

12 53 1 0 0 0 0

12 54 1 0 0 0 0

13 14 1 0 0 0 0

13 20 1 0 0 0 0

13 55 1 0 0 0 0

14 15 1 0 0 0 0

14 16 1 0 0 0 0

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16 17 1 0 0 0 0

16 18 2 0 0 0 0

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23 26 4 0 0 0 0

24 25 1 0 0 0 0

24 30 4 0 0 0 0

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25 60 1 0 0 0 0

26 27 1 0 0 0 0

26 28 4 0 0 0 0

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28 35 1 0 0 0 0

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29 36 1 0 0 0 0

30 31 1 0 0 0 0

31 32 1 0 0 0 0

31 33 1 0 0 0 0

32 37 1 0 0 0 0

32 38 1 0 0 0 0

32 39 1 0 0 0 0

33 40 1 0 0 0 0

33 41 1 0 0 0 0

33 42 1 0 0 0 0

M END): 19 ms

reading 60 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

60 atoms created

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

Script completed

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Molfile expand

Formula

C23H27N3O7

Net Charge

Average Mass

457.47650

Monoisotopic Mass

457.18490

InChI

InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1

InChIKey

DYKFCLLONBREIL-KVUCHLLUSA-N

SMILES

[H][C@@]12Cc3c(ccc(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])C2)N(C)C

Metabolite of Species	Details
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	antibacterial drug A drug used to treat or prevent bacterial infections. Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via tetracyclines ) (via tetracenomycin ) antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via tetracenomycin )

Application(s):	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.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	minocycline (CHEBI:50694) has role Escherichia coli metabolite (CHEBI:76971) minocycline (CHEBI:50694) has role antibacterial drug (CHEBI:36047) minocycline (CHEBI:50694) has role geroprotector (CHEBI:176497) minocycline (CHEBI:50694) is a tertiary α-hydroxy ketone (CHEBI:139592) minocycline (CHEBI:50694) is a tetracenomycin (CHEBI:48132) minocycline (CHEBI:50694) is a tetracyclines (CHEBI:26895) minocycline (CHEBI:50694) is conjugate acid of minocycline(1−) (CHEBI:71337) minocycline (CHEBI:50694) is tautomer of minocycline zwitterion (CHEBI:77906)

Incoming	minocycline hydrochloride (CHEBI:50697) has part minocycline (CHEBI:50694) minocycline(1−) (CHEBI:71337) is conjugate base of minocycline (CHEBI:50694) minocycline zwitterion (CHEBI:77906) is tautomer of minocycline (CHEBI:50694)

IUPAC Name

(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

INNs	Sources
minociclina	DrugBank
minociclinum	DrugBank
minocycline	ChemIDplus

Synonyms	Sources
(4S,4AS,5AR,12AS)-4,7-BIS(DIMETHYLAMINO)-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE	PDBeChem
7-Dimethylamino-6-demethyl-6-deoxytetracycline	ChemIDplus
Minocycline	KEGG COMPOUND
minomycin	ChEBI

Manual Xrefs	Databases
16735907	ChemSpider
1813	DrugCentral
C00018686	KNApSAcK
C07225	KEGG COMPOUND
D05045	KEGG DRUG
DB01017	DrugBank
HMDB0015152	HMDB
LMPK07000002	LIPID MAPS
MIY	PDBeChem
US3226436	Patent
WO2008104734	Patent
View more database links

Registry Numbers	Types	Sources
10118-90-8	CAS Registry Number	KEGG COMPOUND
10118-90-8	CAS Registry Number	ChemIDplus
3077644	Reaxys Registry Number	Reaxys

Citations

Singh S, Khanna D, Kalra S (2021)
Minocycline and Doxycycline: More Than Antibiotics.
Current molecular pharmacology 14, 1046-1065 [PubMed:33568043]
[show Abstract]

Wang P, Farmer JP, Rullo J (2021)
Minocycline-Induced Hyperpigmentation.
JAMA dermatology 157, 992 [PubMed:34232283]

Baldwin HE, Ward DB (2021)
Fifty Years of Minocycline and Its Evolution: A Dermatological Perspective.
Journal of drugs in dermatology : JDD 20, 1031-1036 [PubMed:34636517]
[show Abstract]

Zhou C, Sun R, Sun C, Gu M, Guo C, Zhang J, Du Y, Gu H, Liu Q (2020)
Minocycline protects neurons against glial cells-mediated bilirubin neurotoxicity.
Brain research bulletin 154, 102-105 [PubMed:31733348]
[show Abstract]

Naderi Y, Panahi Y, Barreto GE, Sahebkar A (2020)
Neuroprotective effects of minocycline on focal cerebral ischemia injury: a systematic review.
Neural regeneration research 15, 773-782 [PubMed:31719236]
[show Abstract]

Arezoomandan R, Aliaghaei A, Khodagholi F, Haghparast A (2019)
Minocycline induces the expression of intra-accumbal glutamate transporter-1 in the morphine-dependent rats.
Asian journal of psychiatry 46, 70-73 [PubMed:31630007]
[show Abstract]

Oviedo Briones M, Rico A, Grados M (2017)
[Minocycline induced hyperpigmentation].
Revista espanola de geriatria y gerontologia 52, 353-354 [PubMed:28709717]

Bonilla E, Contreras R, Medina-Leendertz S, Mora M, Villalobos V, Bravo Y (2012)
Minocycline increases the life span and motor activity and decreases lipid peroxidation in manganese treated Drosophila melanogaster.
Toxicology 294, 50-53 [PubMed:22330257]
[show Abstract]

Last Modified

27 October 2021

CHEBI:50694 - minocycline

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