Tetracycline

Details

• Internal ID: 21351984-ec09-4501-9a5e-d26b80b1cbd6
• Taxonomy: Phenylpropanoids and polyketides > Tetracyclines
• IUPAC Name: (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
• InChI: InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
• InChI Key: NWXMGUDVXFXRIG-WESIUVDSSA-N
• Popularity: 16,585 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: -2.00
• Atomic LogP (AlogP): -0.37
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• 60-54-8
• Deschlorobiomycin
• Tetracyclinum
• Achromycin
• Tetracyclin
• Sumycin
• Abramycin
• Tsiklomitsin
• Cyclopar
• Ambramycin
• Liquamycin
• Panmycin
• Tetracyn
• Tetrazyklin
• Achromycin V
• Hostacyclin
• Omegamycin
• Tetradecin
• Tetraverine
• Tsiklomistsin
• Vetacyclinum
• Tetrafil
• Tetra-Co
• Cefracycline
• Criseociclina
• Abricycline
• Agromicina
• Ambramicina
• Biocycline
• Ciclibion
• Copharlan
• Democracin
• Lexacycline
• Limecycline
• Mericycline
• Micycline
• Orlycycline
• Purocyclina
• Roviciclina
• Solvocin
• Tetrabon
• Tetracycl
• Amycin
• Veracin
• Tetracycline HCl
• SK-Tetracycline
• Tetracycline II
• Tetracyclinehydrate
• Cyclomycin
• Tetracycline I
• Bio-tetra
• Tetracycline base
• CHEBI:27902
• Piracaps (base)
• Centet (base)
• (4S,4aS,5aS,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
• (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• NSC-108579
• Cefracycline suspension
• Liquamycin (Veterinary)
• F8VB5M810T
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)-
• Tetraciclina
• DTXSID7023645
• Tetracycline (internal use)
• Supramycin
• Vetquamycin-324 (free base)
• 60-54-8 (FREE BASE)
• E701
• Achromycin (naphthacene derivative)
• T-125
• HSDB 3188
• 6-Methyl-1,11-dioxy-2-naphthacenecarboxamide
• Tetracyclinum [INN-Latin]
• Tetraciclina [INN-Spanish]
• (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
• Sumycin (TN)
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha))-
• UNII-F8VB5M810T
• Economycin
• Vetquamycin
• Brodspec
• Tetracycline (JAN/USP/INN)
• CCRIS 9483
• SR-01000000212
• NSC108579
• Tetrabid Organon
• Ala-Tet
• Tetracycline [USP:INN:BAN:JAN]
• 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-
• EINECS 200-481-9
• MFCD00151232
• Spectrum_001034
• Prestwick0_000140
• Prestwick1_000140
• Prestwick2_000140
• Prestwick3_000140
• Spectrum2_001329
• Spectrum3_000565
• Spectrum4_000352
• Spectrum5_001112
• TETRACYCLINE [MI]
• TETRACYCLINE [INN]
• TETRACYCLINE [JAN]
• EC 200-481-9
• TETRACYCLINE [HSDB]
• SCHEMBL3098
• TETRACYCLINE [VANDF]
• BSPBio_000220
• BSPBio_001950
• KBioGR_000783
• KBioSS_001514
• TETRACYCLINE [MART.]
• BIDD:GT0653
• DivK1c_000827
• SCHEMBL537050
• TETRACYCLINE [WHO-DD]
• SPBio_001457
• SPBio_002159
• BPBio1_000242
• DTXCID703645
• SCHEMBL2116649
• SCHEMBL2116661
• SCHEMBL21271987
• GTPL10927
• KBio1_000827
• KBio2_001514
• KBio2_004082
• KBio2_006650
• KBio3_001450
• TETRACYCLINE [GREEN BOOK]
• NINDS_000827
• NWXMGUDVXFXRIG-WESIUVDSSA-N
• OFVLGDICTFRJMM-WESIUVDSSA-N
• HMS2090B04
• TETRACYCLINE [ORANGE BOOK]
• Tetracycline, >=98.0% (NT)
• TETRACYCLINE [EP MONOGRAPH]
• TETRACYCLINE [USP IMPURITY]
• (4R,4AS,5AS,6S,12AS)-4-(DIMETHYLAMINO)-3,6,10,12,12A-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-3,6,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-, (4S-(4.ALPHA.,4A.ALPHA.,5A.ALPHA.,6.BETA.,12A.ALPHA.))-
• HY-A0107
• PYLERA COMPONENT TETRACYCLINE
• RKL10088
• TETRACYCLINE [USP MONOGRAPH]
• Tetracycline, >=88.0% (HPLC)
• Tox21_300150
• BDBM50237605
• s4490
• AKOS024277860
• AKOS026749977
• CS-8188
• DB00759
• TETRACYCLINE COMPONENT OF PYLERA
• Tetracycline dried down 2.5 microg/mL
• CAS-60-54-8
• IDI1_000827
• NCGC00017323-03
• NCGC00017323-04
• NCGC00017323-05
• NCGC00017323-07
• NCGC00017323-15
• NCGC00142507-02
• NCGC00254063-01
• 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,1 0,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
• BT166207
• SBI-0051530.P003
• LYMECYCLINE IMPURITY H [EP IMPURITY]
• T3971
• C06570
• D00201
• EN300-374118
• AB00053550-04
• AB00053550_05
• AB00053550_06
• Q193045
• SR-01000000212-3
• Z2144222809
• OXYTETRACYCLINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
• (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9465	94.65%
Caco-2	+	0.8145	81.45%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5756	57.56%
OATP2B1 inhibitior	+	0.5400	54.00%
OATP1B1 inhibitior	+	0.9270	92.70%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8216	82.16%
P-glycoprotein inhibitior	-	0.8691	86.91%
P-glycoprotein substrate	+	0.8484	84.84%
CYP3A4 substrate	+	0.6003	60.03%
CYP2C9 substrate	-	0.8536	85.36%
CYP2D6 substrate	-	0.8280	82.80%
CYP3A4 inhibition	-	0.8686	86.86%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9089	90.89%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.7810	78.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7140	71.40%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9606	96.06%
Skin irritation	-	0.7792	77.92%
Skin corrosion	-	0.9221	92.21%
Ames mutagenesis	-	0.5228	52.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.3965	39.65%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.8478	84.78%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.7701	77.01%
Acute Oral Toxicity (c)	III	0.7834	78.34%
Estrogen receptor binding	-	0.6370	63.70%
Androgen receptor binding	+	0.6158	61.58%
Thyroid receptor binding	-	0.6682	66.82%
Glucocorticoid receptor binding	-	0.6092	60.92%
Aromatase binding	-	0.5200	52.00%
PPAR gamma	+	0.5776	57.76%
Honey bee toxicity	-	0.8977	89.77%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9715	97.15%

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	98.43%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.35%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.61%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.66%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.97%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	88.32%	94.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.28%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	87.10%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.72%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.39%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.90%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.58%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.66%	86.33%
CHEMBL4208	P20618	Proteasome component C5	81.96%	90.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54675776
• LOTUS: LTS0227773
• wikiData: Q193045