Lincomycin

Details

• Internal ID: ecb47bd9-44e6-426f-ac71-33f3f368c5e8
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Proline and derivatives
• IUPAC Name: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
• SMILES (Canonical): CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)O
• SMILES (Isomeric): CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@@H](C)O
• InChI: InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
• InChI Key: OJMMVQQUTAEWLP-KIDUDLJLSA-N
• Popularity: 6,341 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₄N₂O₆S
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.21375798 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.86
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• 154-21-2
• Cillimycin
• Lincolnensin
• Lincomicina
• Lincomycinum
• Jiemycin
• Lincomycin A
• Lincolcina
• BOD072YW0F
• U-10149
• U 10,149A
• U-10,149
• CHEBI:6472
• DTXSID3023215
• (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
• Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-alpha-D-galacto-octopyranoside
• (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide
• D-erythro-alpha-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-(((1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-, (2S-trans)-
• (2S,4R)-N-((1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl)propyl)-1-methyl-4-propyl-pyrrolidine-2-carboxamide
• (2S,4R)-N-((1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide
• METHYL 6,8-DIDEOXY-6-((((2S,4R)-1-METHYL-4-PROPYLPYRROLIDIN-2-YL)CARBONYL)AMINO)-1-THIO-D-ERYTHRO-alpha-D-GALACTO-OCTOPYRANOSIDE
• methyl 6,8-dideoxy-6-({[(2S,4R)-1-methyl-4-propylpyrrolidin-2-yl]carbonyl}amino)-1-thio-D-erythro-alpha-D-galacto-octopyranoside
• LincoMed 300
• RefChem:55509
• Lincomycin Injectable 30%
• Lincomycin Injectable, USP
• DTXCID003215
• J01FF02
• LINCOMIX 20, LINCOMIX 50
• Hemihydrate Lincomycin Monohydrochloride
• LINCOMYCIN 100, LINCOMYCIN 25, LINCOMYCIN 300
• 205-824-6
• Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-D-galacto-octopyranoside (alpha-
• Lincocin
• Lincomycin (USAN/INN)
• CHEMBL1447
• Frademicina
• (2S,4R)-N-((1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide
• Lincomycin (hydrochloride)
• C18H34N2O6S
• LCM
• Lincomycine [French]
• NSC 70731
• U10149A
• AC1MHD7X
• Lincomycine [INN-French]
• Lincomycinum [INN-Latin]
• UNII-BOD072YW0F
• Lincomicina [INN-Spanish]
• Bactramycin
• Lincorex
• Lincomycin [USAN:INN:BAN]
• Lincomycin, (2S-cis)-Isomer
• HSDB 3109
• L-Mycin
• 3QB
• methyl 6,8-dideoxy-6-{[(4R)-1-methyl-4-propyl-L-prolyl]amino}-1-thio-D-erythro-alpha-D-galacto-octopyranoside
• EINECS 205-824-6
• BRN 0707677
• LINCOMYCIN [MI]
• LINCOMYCIN [INN]
• LINCOMYCIN [HSDB]
• LINCOMYCIN [USAN]
• Clindamycin EP Impurity A
• LINCOMYCIN [VANDF]
• LINCOMYCIN [MART.]
• SCHEMBL4010
• LINCOMYCIN [WHO-DD]
• (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
• orb1708945
• LINCOMYCIN [GREEN BOOK]
• LINCOMYCIN [ORANGE BOOK]
• GTPL10941
• LINCOMYCIN [USP IMPURITY]
• HMS2089A13
• Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-.alpha.-D-galacto-octopyranoside
• BDBM50335522
• EBC-13871
• MFCD00135816
• T1235L
• AKOS015951392
• AL76787
• CCG-208231
• DB01627
• SMP1_000178
• NCGC00159326-11
• D-erythro-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-, trans-alpha-
• Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-D-galacto-octopyranoside (alpha-form)
• HY-117660
• CS-0066775
• NS00000025
• C06812
• D00223
• EN300-118720
• AB01275426-01
• CLINDAMYCIN HYDROCHLORIDE IMPURITY A [IP]
• F608586
• Q423428
• BRD-K49384696-003-01-9
• CLINDAMYCIN PHOSPHATE IMPURITY A [EP IMPURITY]
• Z1515385088
• CLINDAMYCIN HYDROCHLORIDE IMPURITY A [EP IMPURITY]
• (2S,4R)-N-((1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)-tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide
• (2S,4R)-N-((1S)-2-hydroxy-1-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)-tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide
• (2S-TRANS)-METHYL 6,8-DIDEOXY-6-(((1-METHYL-4-PROPYL-2-PYRROLIDINYL)CARBONYL)AMINO)-1-THIO-D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE
• 1-Methyl-4-propyl-pyrrolidine-2-carboxylic acid [2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide
• Clindamycin Phosphate EP Impurity A; Lincomycin(Base); Clindamycin Hydrochloride EP Impurity A
• D-Erythro-.alpha.-D-gluco-octopyranoside, methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-
• D-erythro-alpha-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-((((2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-
• Methyl (5r)-5-[(1r,2r)-2-Hydroxy-1-{[(4r)-1-Methyl-4-Propyl-L-Prolyl]amino}propyl]-1-Thio-Beta-L-Arabinopyranoside
• METHYL 6,8-DIDEOXY-6-((((2S,4R)-1-METHYL-4-PROPYLPYRROLIDIN-2-YL)CARBONYL)AMINO)-1-THIO-D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9658	96.58%
Caco-2	-	0.7523	75.23%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Lysosomes	0.5026	50.26%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.9393	93.93%
OATP1B3 inhibitior	+	0.9289	92.89%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8621	86.21%
P-glycoprotein inhibitior	-	0.8547	85.47%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.7160	71.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7952	79.52%
CYP3A4 inhibition	-	0.9342	93.42%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9203	92.03%
CYP2D6 inhibition	-	0.9269	92.69%
CYP1A2 inhibition	-	0.9222	92.22%
CYP2C8 inhibition	-	0.9844	98.44%
CYP inhibitory promiscuity	-	0.9563	95.63%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6495	64.95%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9902	99.02%
Skin irritation	-	0.7575	75.75%
Skin corrosion	-	0.9137	91.37%
Ames mutagenesis	-	0.7337	73.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.7971	79.71%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.8580	85.80%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.6324	63.24%
Acute Oral Toxicity (c)	III	0.7675	76.75%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	+	0.5669	56.69%
Glucocorticoid receptor binding	-	0.8661	86.61%
Aromatase binding	+	0.5519	55.19%
PPAR gamma	-	0.6326	63.26%
Honey bee toxicity	-	0.7634	76.34%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	-	0.4904	49.04%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	63.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.40%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.59%	97.25%
CHEMBL2581	P07339	Cathepsin D	97.23%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.87%	90.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	94.24%	97.21%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	94.05%	95.58%
CHEMBL321	P14780	Matrix metalloproteinase 9	93.51%	92.12%
CHEMBL3359	P21462	Formyl peptide receptor 1	93.20%	93.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	92.49%	98.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.42%	90.71%
CHEMBL4588	P22894	Matrix metalloproteinase 8	92.39%	94.66%
CHEMBL332	P03956	Matrix metalloproteinase-1	91.05%	94.50%
CHEMBL230	P35354	Cyclooxygenase-2	90.70%	89.63%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.50%	95.17%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	90.44%	97.50%
CHEMBL240	Q12809	HERG	89.97%	89.76%
CHEMBL220	P22303	Acetylcholinesterase	89.90%	94.45%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	89.77%	95.71%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	89.54%	92.86%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	89.32%	92.29%
CHEMBL4040	P28482	MAP kinase ERK2	89.01%	83.82%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.52%	96.95%
CHEMBL2094135	Q96BI3	Gamma-secretase	88.48%	98.05%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.44%	96.47%
CHEMBL4073	P09237	Matrix metalloproteinase 7	88.22%	97.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.61%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.56%	95.89%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	87.47%	98.46%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.31%	99.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.08%	100.00%
CHEMBL274	P51681	C-C chemokine receptor type 5	86.67%	98.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.55%	89.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.95%	89.34%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.88%	96.61%
CHEMBL4208	P20618	Proteasome component C5	85.86%	90.00%
CHEMBL2514	O95665	Neurotensin receptor 2	85.28%	100.00%
CHEMBL255	P29275	Adenosine A2b receptor	85.12%	98.59%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.12%	96.38%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	83.10%	99.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.07%	92.50%
CHEMBL333	P08253	Matrix metalloproteinase-2	82.98%	96.31%
CHEMBL256	P0DMS8	Adenosine A3 receptor	82.38%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.29%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.95%	91.19%
CHEMBL283	P08254	Matrix metalloproteinase 3	80.55%	97.29%
CHEMBL1075317	P61964	WD repeat-containing protein 5	80.02%	96.33%

Plants that contains it

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Cross-Links

• PubChem: 3000540
• LOTUS: LTS0199247
• wikiData: Q423428