Demeclocycline (CED0007706)

Record Information

Version

1.0

Creation Date

2014-08-28 19:27:37 UTC

Update Date

2026-05-14 16:44:14 UTC

SynCED ID

CED0007706

Secondary Accession Numbers

CHEM002911
T3D3951

Identification

Common Name

Demeclocycline

Class

Small Molecule

Description

Demeclocycline belongs to the tetracyclines, a class of phenylpropanoids and polyketides within the organic compounds. This exogenous compound has the formula C21H21ClN2O8 and an average molecular weight of 464.85 g/mol. At room temperature, it exists as a solid. Demeclocycline is utilized as an antibacterial drug and is found in healthcare, pharmaceuticals, and veterinary products specifically among antibiotics and tetracyclines. The recorded exposure route for this compound is oral. Within the body, it has been detected in the heart, liver, and bone marrow. In terms of its biological activity, it acts as an inhibitor of the Vasopressin V2 receptor (AVPR2).

Contaminant Type

Anti-Bacterial Agent
Drug
Metabolite
Organic Compound
Synthetic Compound
Tetracycline

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-Demethyl-7-chlorotetracycline	ChEBI
7-Chloro-6-demethyltetracycline	ChEBI
[4S-(4alpha,4Aalpha,5aalpha,6beta,12aalpha)]-7-chloro-4-(dimethylamino)1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide	ChEBI
Demeclociclina	ChEBI
Demeclocyclinum	ChEBI
Demethylchlortetracycline	ChEBI
DMCT	ChEBI
DMCTC	ChEBI
[4S-(4a,4Aalpha,5aalpha,6b,12aalpha)]-7-chloro-4-(dimethylamino)1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide	Generator
[4S-(4Α,4aalpha,5aalpha,6β,12aalpha)]-7-chloro-4-(dimethylamino)1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide	Generator
6-Demethylchlorotetracycline	HMDB
Demethylchlorotetracycline	HMDB
Demethylchlortetracyclin	HMDB
Demethylchlortetracyclinum	HMDB
Methylchlorotetracycline	HMDB
Tri-demethylchlortetracycline	HMDB

Chemical Formula

C₂₁H₂₁ClN₂O₈

Average Molecular Mass

464.853 g/mol

Monoisotopic Mass

464.099 g/mol

CAS Registry Number

127-33-3

IUPAC Name

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

Traditional Name

demeclocycline

SMILES

[H][C@]12C[C@@]3([H])[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C(=O)C1=C([C@H]2O)C(Cl)=CC=C1O

InChI Identifier

InChI=1S/C21H21ClN2O8/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1

InChI Key

FMTDIUIBLCQGJB-SEYHBJAFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tetracyclines

Sub Class

Not Available

Direct Parent

Tetracyclines

Alternative Parents

Substituents

Tetracycline
Tetracene
Naphthacene
Anthracene carboxylic acid or derivatives
Tetralin
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Aralkylamine
Aryl chloride
Aryl halide
Benzenoid
Tertiary alcohol
Vinylogous acid
Carboxamide group
Amino acid or derivatives
Tertiary amine
Secondary alcohol
Primary carboxylic acid amide
Tertiary aliphatic amine
Ketone
Carboxylic acid derivative
Enol
Polyol
Organooxygen compound
Organic nitrogen compound
Amine
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organohalogen compound
Organochloride
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

tetracyclines (CHEBI:4392 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Bone Marrow
Heart
Liver

Applications

antibacterial drug

Biological Roles

antibacterial drug ?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	220-223°C
Boiling Point	Not Available
Solubility	1520 mg/L (at 21°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.53 g/L	ALOGPS
logP	-0.4	ALOGPS
logP	-3.2	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	-2.6	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	114.35 m³·mol⁻¹	ChemAxon
Polarizability	43.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-9378400000-329aa1208117aab0f5e4	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-1000-4010091000-c8e0c401309a9457563b	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kb-0000900000-8c58dc160e3ba638d92d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000t-0000900000-a779de3a79a402d35f64	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0040-2169800000-5312c1175cabffae7003	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0000900000-b1c5caf8c7a1c0f220c5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0w91-0002900000-215d2308de52f38ae15c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9166000000-d2735acbcbfa1a93efd2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kb-0000900000-34564ceb210387de33e4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0000900000-fde2bfb10ade341c4143	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052u-4619400000-d50ccc394c468f134b28	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0001900000-313f2690b1b4b1750c3a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-7039800000-fa843a609f56e5c2ae51	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001l-7059700000-3fa3ce3dfc5f6d5a7187	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2176.0 Log mg/kg [1200:3900]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Tetracyclines target the 28S small subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result tetracyclines are cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. (2). The likely target of most tetracyclines is the 12S rRNA molecule in the mitochondrial ribosome, which is analogous to the 16S rRNA in bacterial ribosomes. Oral, rat: LD50 = 2372 mg/kg

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Drug therapy is discontinued immediately; exchange transfusion may be required to remove the drug. Sometimes, phenobarbital (UGT induction) is used.

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000306	Antibiotics?Antibiotics are synthetic or semi-synthetic compounds used to treat bacterial infections in humans and animals.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000338	Tetracyclines?Tetracyclines are a class of broad-spectrum antibiotics that are widely used in both human and veterinary medicine.	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

4 pathwaysPathway Source: PathBank

Demeclocycline Action Pathway

Demeclocycline Drug Metabolism Action Pathway

Demeclocycline Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Multidrug transporter MdfA	P0AEY8	Escherichia coli K-12	Predicted (SEA)	Prediction Confidence Score 0.4 Applicability Domain 0.481 Statistical Significance 6.00e-05 Supporting Reference Compounds 2 E-value 0.467095
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	Prediction Confidence Score 0.319 Applicability Domain 0.589 Statistical Significance 0.0118 Supporting Reference Compounds 425 E-value 91.7064
Click to view 3D structure	P2Y purinoceptor 12	Q9H244	Humans	Predicted (SEA)	Prediction Confidence Score 0.251 Applicability Domain 0.583 Statistical Significance 0.0066 Supporting Reference Compounds 49 E-value 51.7697
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.589 Statistical Significance 0.1019 Supporting Reference Compounds 343 E-value 793.128
Click to view 3D structure	Protein Tat	P04608	Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1)	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.589 Statistical Significance 0.0221 Supporting Reference Compounds 108 E-value 172.047
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 7	P35236	Humans	Predicted (SEA)	Prediction Confidence Score 0.231 Applicability Domain 0.583 Statistical Significance 0.0959 Supporting Reference Compounds 130 E-value 746.808
Click to view 3D structure	Alpha-synuclein	P37840	Humans	Predicted (SEA)	Prediction Confidence Score 0.22 Applicability Domain 0.583 Statistical Significance 0.0143 Supporting Reference Compounds 38 E-value 111.48
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	O75469	Humans	Predicted (SEA)	Prediction Confidence Score 0.218 Applicability Domain 0.474 Statistical Significance 0.1475 Supporting Reference Compounds 146 E-value 1148.28
Click to view 3D structure	DNA repair protein RAD52 homolog	P43351	Humans	Predicted (SEA)	Prediction Confidence Score 0.207 Applicability Domain 0.474 Statistical Significance 0.005 Supporting Reference Compounds 17 E-value 39.236
Click to view 3D structure	NAD-dependent protein deacylase sirtuin-5, mitochondrial	Q9NXA8	Humans	Predicted (SEA)	Prediction Confidence Score 0.2 Applicability Domain 0.481 Statistical Significance 0.0056 Supporting Reference Compounds 14 E-value 43.5177
Click to view 3D structure	DNA topoisomerase 2-alpha	P11388	Humans	Predicted (SEA)	Prediction Confidence Score 0.195 Applicability Domain 0.204 Low confidence Statistical Significance 0.0514 Supporting Reference Compounds 27 E-value 399.989
Click to view 3D structure	Isoleucyl-tRNA synthetase	O35880	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.194 Applicability Domain 0.204 Low confidence Statistical Significance 5.80e-04 Supporting Reference Compounds 3 E-value 4.51525
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.19 Applicability Domain 0.214 Low confidence Statistical Significance 0.4035 Supporting Reference Compounds 199 E-value 3141.06
Click to view 3D structure	Protein kinase C-like 1	P43057	Candida albicans	Predicted (SEA)	Prediction Confidence Score 0.188 Applicability Domain 0.188 Low confidence Statistical Significance 5.00e-04 Supporting Reference Compounds 1 E-value 3.89246
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	Prediction Confidence Score 0.188 Applicability Domain 0.205 Low confidence Statistical Significance 0.9447 Supporting Reference Compounds 1301 E-value 7354.57
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	Prediction Confidence Score 0.187 Applicability Domain 0.198 Low confidence Statistical Significance 0.5924 Supporting Reference Compounds 215 E-value 4612.18
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.186 Applicability Domain 0.194 Low confidence Statistical Significance 0.9652 Supporting Reference Compounds 1130 E-value 7514.24
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.191 Low confidence Statistical Significance 0.7608 Supporting Reference Compounds 472 E-value 5922.92
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.205 Low confidence Statistical Significance 0.9553 Supporting Reference Compounds 1660 E-value 7436.94
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.194 Low confidence Statistical Significance 0.9807 Supporting Reference Compounds 1538 E-value 7634.75
Click to view 3D structure	Aurora kinase A	O14965	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.194 Low confidence Statistical Significance 0.9332 Supporting Reference Compounds 996 E-value 7265.04
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.194 Low confidence Statistical Significance 0.9361 Supporting Reference Compounds 1017 E-value 7287.23
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.194 Low confidence Statistical Significance 0.9756 Supporting Reference Compounds 1245 E-value 7594.66
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	Prediction Confidence Score 0.182 Applicability Domain 0.194 Low confidence Statistical Significance 0.9558 Supporting Reference Compounds 793 E-value 7441.06
Click to view 3D structure	Tyrosine-protein kinase Fyn	P06241	Humans	Predicted (SEA)	Prediction Confidence Score 0.182 Applicability Domain 0.194 Low confidence Statistical Significance 0.9301 Supporting Reference Compounds 707 E-value 7240.52

Concentrations

Not Available

External Links

DrugBank ID

DB00618

HMDB ID

HMDB0014756

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Demeclocycline

Chemspider ID

10482117

ChEBI ID

4392

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

McCormick, J.R.D., Hirsch, U., Jensen, E.R. and Sjolander, N.O.; U.S. Patent 2,878,289; March 17, 1959; assigned to American Cyanamid Company.
Szumski, S.A.; U.S. Patent 3,012,946; December 12,1961; assigned to American Cyanamid Company.
Goodman, J.J. and Matrishin, M.; U.S. Patent 3,019,172; assigned to American Cyanamid Company.
Goodman, J.J.; U.S. Patent 3,050,446; August 21, 1962; assigned to American Cyanamid Company.
Neidleman, S. L.; US. Patent 3,154,476; October 27,1964; assigned to Olin Mathieson Chemical Corporation.

MSDS

Link

General References

De Troyer A, Demanet JC: Correction of antidiuresis by demeclocycline. N Engl J Med. 1975 Oct 30;293(18):915-8. [PubMed: 170519]
McKee EE, Ferguson M, Bentley AT, Marks TA: Inhibition of mammalian mitochondrial protein synthesis by oxazolidinones. Antimicrob Agents Chemother. 2006 Jun;50(6):2042-9. [PubMed: 16723564]
Wikipedia. Demeclocycline. Last updated on 20 May 2014. - http://en.wikipedia.org/wiki/Demeclocycline

Demeclocycline (CED0007706)

Structure for CHEM002911: Demeclocycline

Structure