Methicillin

Details

• Internal ID: cc4b8365-f42d-4d8b-b6fe-5e2ae6e5c2fa
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Dipeptides
• IUPAC Name: (2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• SMILES (Canonical): CC1(C(N2C(S1)C(C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)O)C
• SMILES (Isomeric): CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)O)C
• InChI: InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
• InChI Key: RJQXTJLFIWVMTO-TYNCELHUSA-N
• Popularity: 18,476 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀N₂O₆S
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.10420754 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.95
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Meticillin
• Methycillin
• 61-32-5
• Methicillinum
• Meticilina
• Meticilline
• Meticillinum
• Staphcillin
• Metacillin
• Dimocillin
• Meticilina [INN-Spanish]
• Meticilline [INN-French]
• Meticillinum [INN-Latin]
• (2,6-Dimethoxyphenyl)penicillin
• 6-(2,6-Dimethoxybenzamido)penicillanic acid
• CHEBI:6827
• (2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• BRL 1241
• 6beta-(2,6-dimethoxybenzamido)penicillanic acid
• 2,6-dimethoxyphenyl penicillin
• Meticillina
• Q91FH1328A
• Celbenin
• (2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Meticillina [DCIT]
• Methcillin
• Meticillin [INN]
• Methicillin [USAN]
• HSDB 3121
• Meticillin [INN:BAN]
• EINECS 200-505-8
• Penicillin, (2,6-dimethoxyphenyl)-
• UNII-Q91FH1328A
• (2S,5R,6R)-6-(2,6-DIMETHOXYBENZAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((2,6-dimethoxybenzoyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
• Spectrum_000993
• Spectrum2_001965
• Spectrum3_000494
• Spectrum4_000878
• Spectrum5_001600
• METICILLIN [HSDB]
• CHEMBL575
• Epitope ID:139649
• METHICILLIN [VANDF]
• SCHEMBL4898
• METICILLIN [WHO-DD]
• BSPBio_001987
• KBioGR_001575
• KBioSS_001473
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-
• 6-(2,3-Dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• DivK1c_000100
• SPBio_002089
• DTXSID6023284
• GTPL12264
• KBio1_000100
• KBio2_001473
• KBio2_004041
• KBio2_006609
• KBio3_001487
• NINDS_000100
• RJQXTJLFIWVMTO-TYNCELHUSA-N
• BDBM50103523
• 6beta-(2,6-dimethoxybenzamido)-2,2-dimethylpenam-3alpha-carboxylic acid
• AKOS030530774
• DB01603
• IDI1_000100
• (2S,5R,6R)-6-{[(2,6-dimethoxyphenyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2,6-dimethoxybenzamido)-3,3,-dimethyl-7-oxo-
• MII
• SBI-0051440.P003
• HY-121544
• MRSA Selective Supplement, for microbiology
• CS-0082724
• C07177
• EN300-19748934
• Q409262
• BRD-K34388247-236-02-5
• (2S,5R,6R)-6-[(2,6-dimethoxybenzene)amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8534	85.34%
Caco-2	-	0.7386	73.86%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5285	52.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9456	94.56%
OATP1B3 inhibitior	+	0.9363	93.63%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4672	46.72%
P-glycoprotein inhibitior	-	0.7855	78.55%
P-glycoprotein substrate	-	0.7338	73.38%
CYP3A4 substrate	+	0.6090	60.90%
CYP2C9 substrate	-	0.6345	63.45%
CYP2D6 substrate	-	0.8718	87.18%
CYP3A4 inhibition	-	0.7747	77.47%
CYP2C9 inhibition	-	0.8793	87.93%
CYP2C19 inhibition	-	0.8738	87.38%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.8626	86.26%
CYP2C8 inhibition	-	0.9402	94.02%
CYP inhibitory promiscuity	-	0.9500	95.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5600	56.00%
Carcinogenicity (trinary)	Non-required	0.6828	68.28%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9554	95.54%
Skin irritation	-	0.7486	74.86%
Skin corrosion	-	0.9295	92.95%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7727	77.27%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.6766	67.66%
skin sensitisation	-	0.7829	78.29%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.7366	73.66%
Acute Oral Toxicity (c)	IV	0.4681	46.81%
Estrogen receptor binding	-	0.4853	48.53%
Androgen receptor binding	-	0.7249	72.49%
Thyroid receptor binding	-	0.5540	55.40%
Glucocorticoid receptor binding	+	0.6469	64.69%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.5249	52.49%
Honey bee toxicity	-	0.8869	88.69%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9324	93.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.18%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.68%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.91%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.11%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	88.79%	90.17%
CHEMBL2581	P07339	Cathepsin D	88.51%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	86.77%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.42%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.17%	81.11%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.89%	91.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	84.43%	87.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.24%	97.14%
CHEMBL2535	P11166	Glucose transporter	81.54%	98.75%
CHEMBL5028	O14672	ADAM10	81.10%	97.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.68%	82.69%

Plants that contains it

• Huperzia lucidula
• Lycopodium deuterodensum
• Tanacetum argenteum

Cross-Links

• PubChem: 6087
• LOTUS: LTS0167701
• wikiData: Q409262