Doxycycline

Details

• Internal ID: 128d5b80-ee3a-49c2-afa0-4eb796a8093b
• Taxonomy: Phenylpropanoids and polyketides > Tetracyclines
• IUPAC Name: (4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• SMILES (Canonical): CC1C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
• SMILES (Isomeric): C[C@@H]1[C@H]2[C@@H]([C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
• 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/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
• InChI Key: SGKRLCUYIXIAHR-AKNGSSGZSA-N
• Popularity: 10,968 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄N₂O₈
• Molecular Weight: 444.40 g/mol
• Exact Mass: 444.15326573 g/mol
• Topological Polar Surface Area (TPSA): 182.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.50
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• 564-25-0
• Vibramycin
• Doxytetracycline
• Doxycycline (anhydrous)
• Doxiciclina
• Doxycyclinum
• Monodox
• Doxycycline anhydrous
• Doxycycline hyclate
• 6alpha-Deoxy-5-oxytetracycline
• 5-Hydroxy-alpha-6-deoxytetracycline
• Vibramycine
• Doxychel
• Anhydrous doxycycline
• 6-alpha-Deoxy-5-oxytetracycline
• Doxycyclin
• alpha-6-Deoxy-5-hydroxytetracycline
• BMY-28689
• Liviatin
• Doxycycline (INN)
• CHEBI:50845
• Doxy-Caps
• Doxycycline (hyclate)
• 6-Deoxytetracycline
• Deoxymykoin
• Dossiciclina
• Doxitard
• Doxivetin
• Doxycen
• Investin
• Doxy-Puren
• alpha-Doxycycline
• Doxy-Tabs
• alpha-6-Deoxyoxytetracycline
• MMV000011
• (4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• Doxysol
• Jenacyclin
• 6-Deoxyoxytetracycline
• Dossiciclina [DCIT]
• Doxiciclina [Italian]
• DOXYCYCLINE [INN]
• (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
• 2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aR,5S,5aR,6R,12aS)-
• Doxycyclinum [INN-Latin]
• Doxycycline (internal use)
• Doxiciclina [INN-Spanish]
• 334895S862
• BU-3839T
• Zenavod
• 24390-14-5
• DOXCYCLINE ANHYDROUS
• Oxytetracycline, 6-deoxy-
• Doxycycline (TN)
• Doxychel (TN)
• Vivox (*Hyclate)
• DMSC (*Fosfatex)
• NSC633557
• HSDB 3071
• Monodox (*monohydrate)
• BMY28689
• BU 3839T
• EINECS 209-271-1
• BMY 28689
• Vibramycin (*monohydrate)
• 4-Epioxytetracycline, 6-deoxy-
• GS-3065 (*monohydrate)
• Doxycycline [USAN:INN:BAN]
• SR-01000075844
• UNII-334895S862
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S-(4alpha,4aalpha,5alpha,5aalpha,6alpha,12aalpha))-
• AB08 (*Fosfatex)
• Spectrum_000807
• (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-carboxaMidehydrochloride
• Spectrum2_000143
• Spectrum3_000408
• Spectrum4_000527
• Spectrum5_000947
• DOXYCYCLINE [HSDB]
• UPCMLD-DP021
• Vibramycin, Doxytetracycline
• CHEMBL1433
• Doxycycline hydrochloride hemiethanolate hemihydrate;WC2031
• Lopac0_000405
• SCHEMBL40930
• SCHEMBL66828
• BSPBio_001936
• DOXYCYCLINE [WHO-DD]
• KBioGR_001133
• KBioSS_001287
• BIDD:GT0146
• DivK1c_000345
• SPBio_000246
• CHEMBL436921
• GTPL6464
• SCHEMBL1176275
• DTXSID0037653
• SCHEMBL17826665
• SCHEMBL19270298
• SCHEMBL21753474
• UPCMLD-DP021:001
• BCBcMAP01_000024
• KBio1_000345
• KBio2_001287
• KBio2_003855
• KBio2_006423
• KBio3_001156
• DTXSID80992212
• JBIWCJUYHHGXTC-AKNGSSGZSA-N
• NINDS_000345
• RPRXAHFLWOCXQL-AKNGSSGZSA-N
• SGKRLCUYIXIAHR-AKNGSSGZSA-N
• DOXYCYCLINE ANHYDROUS [MI]
• HMS2090E06
• DOXYTETRACYCLINE; DOXYCYCLINE
• HY-N0565
• BDBM50592896
• LMPK07000001
• s5159
• ANHYDROUS DOXYCYCLINE [MART.]
• AKOS015900372
• CCG-204498
• DB00254
• SDCCGSBI-0050391.P005
• IDI1_000345
• SMP1_000107
• NCGC00161602-01
• NCGC00161602-03
• NCGC00161602-04
• NCGC00161602-05
• NCGC00161602-07
• NCGC00161602-14
• NCGC00188979-01
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aR,5S,5aR,6R,12aS)
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aR,5S,5aR,6R,12aS)-
• 2-Naphthacenecarboxamide, 4-alpha-S-(dimethylamino)-1,4,4a-alpha-5,5a-alpha,6,11,12a-octahydro-3,5-alpha,10,12,12a-alpha-pentahydroxy-6-alpha-methyl-1,11-dioxo-
• AS-13499
• SBI-0050391.P004
• Doxycycline 1000 microg/mL in Acetonitrile
• CS-0009105
• EN300-58337
• C06973
• D07876
• AB00053465-03
• AB00053465_04
• AB00053465_05
• A817263
• Doxycycline, Antibiotic for Culture Media Use Only
• Q422442
• SR-01000075844-7
• Vibramycin;Doxytetracycline;Doxiciclina;Doxycyclinum
• W-105517
• SR-01000075844-18
• (4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• 2-NAPHTHACENECARBOXAMIDE, 4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-, (4S-(4.ALPHA.,4A.ALPHA.,5.ALPHA.,5A.ALPHA.,6.ALPHA.,12A.ALPHA.))-
• 4-(Dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid
• 7164-70-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9586	95.86%
Caco-2	-	0.9005	90.05%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	+	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7882	78.82%
OATP2B1 inhibitior	-	0.5260	52.60%
OATP1B1 inhibitior	+	0.9209	92.09%
OATP1B3 inhibitior	+	0.9454	94.54%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7978	79.78%
P-glycoprotein inhibitior	-	0.8704	87.04%
P-glycoprotein substrate	+	0.7165	71.65%
CYP3A4 substrate	+	0.6478	64.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8372	83.72%
CYP3A4 inhibition	-	0.8567	85.67%
CYP2C9 inhibition	-	0.9144	91.44%
CYP2C19 inhibition	-	0.9099	90.99%
CYP2D6 inhibition	-	0.9293	92.93%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.8086	80.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9311	93.11%
Carcinogenicity (trinary)	Non-required	0.7022	70.22%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9453	94.53%
Skin irritation	-	0.7972	79.72%
Skin corrosion	-	0.9279	92.79%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3636	36.36%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.8625	86.25%
skin sensitisation	-	0.8563	85.63%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.7686	76.86%
Acute Oral Toxicity (c)	III	0.7981	79.81%
Estrogen receptor binding	-	0.6837	68.37%
Androgen receptor binding	-	0.7799	77.99%
Thyroid receptor binding	-	0.6897	68.97%
Glucocorticoid receptor binding	-	0.6188	61.88%
Aromatase binding	-	0.5886	58.86%
PPAR gamma	+	0.5357	53.57%
Honey bee toxicity	-	0.8969	89.69%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9380	93.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.97%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.87%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.94%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.59%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.17%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.67%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.50%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	84.20%	90.17%
CHEMBL2535	P11166	Glucose transporter	83.40%	98.75%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.32%	100.00%
CHEMBL4422	O14842	Free fatty acid receptor 1	82.57%	93.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.59%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.77%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54671203
• LOTUS: LTS0124854
• wikiData: Q422442