AIC

(2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID

Created:	2001-02-17
Last modified:	2020-06-05

Find Related PDB Entry
9 entries where AIC is found as a standalone ligand

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	43
Chiral Atom Count	4
Bond Count	45
Aromatic Bond Count	6

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	(2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
Synonyms	AMPICILLIN; D(-)-ALPHA-AMINOBENZYLPENICILLIN; 6-[D(-)-ALPHA-AMINOPHENYLLACETAMIDO]PENICILLANIC ACID
Systematic Name (OpenEye OEToolkits)	(2S,5R,6R)-6-[[(2R)-2-amino-2-phenyl-ethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Formula	C₁₆ H₁₉ N₃ O₄ S
Molecular Weight	349.405
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C2N3C(=O)C(NC(=O)C(c1ccccc1)N)C3SC2(C)C
SMILES	CACTVS	3.341	CC1(C)S[CH]2[CH](NC(=O)[CH](N)c3ccccc3)C(=O)N2[CH]1C(O)=O
SMILES	OpenEye OEToolkits	1.5.0	CC1(C(N2C(S1)C(C2=O)NC(=O)C(c3ccccc3)N)C(=O)O)C
Canonical SMILES	CACTVS	3.341	CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c3ccccc3)N)C(=O)O)C
InChI	InChI	1.03	InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChIKey	InChI	1.03	AVKUERGKIZMTKX-NJBDSQKTSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB00415 ?
Name	Ampicillin
Groups	approved vet_approved
Description	Ampicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.
Synonyms	Ampicillin sodium Anhydrous ampicillin Aminobenzylpenicillin Ampicillin, anhydrous D-(?)-6-(α-aminophenylacetamido)penicillanic acid Ampicillin AP Ampicilline Ampicillin acid Ampicilina Ampicillin anhydrous Ampicillin (anhydrous) Ampicillin trihydrate ABPC D-(?)-ampicillin Ampicillinum
Brand Names	Nu-ampi Capsules 250mg Ampicillin for Injection Novo-ampicillin Pws 500mg/5ml Penbritin Inj 1000mg Pro Biosan Kit Ampicillin Sodium Ampicin Inj 2000mg Penbritin Cap 250mg Penbritin Pws 250mg/5ml Ampicillin Trihydrate Apo Ampi Liq 250mg/5ml Nu-ampi Capsules 500mg Nu-ampi Suspension 250mg/5ml Novo-ampicillin Sus 125mg/5ml Ampicillin and Sulbactam Ampicillin Sodium for Injection, BP Apo Ampi Liq 125mg/5ml Penbritin-125 Pws 125mg/vial Sterile Ampicillin Sodium 250mg USP Ampicillin sodium Nu-ampi Sus 125mg/5ml Pro Ampi 500 Cap 500mg Apo Ampi Capsules 250mg Pro Ampi 250 Cap 250mg Unasyn Ampicin Inj 500mg Taro-ampicillin Cap 250mg Ampicin Inj 1gm Penbritin Inj 500mg Penbritin Cap 500mg Ampicillin Sodium and Sulbactam Sodium Jaa Amp Tab 125mg Teva-ampicillin Penbritin-250 Pws Im/iv 250mg/vial Ampicin Inj 125mg/vial Penbritin Inj 250mg Ampicillin Sodium for Injection, USP Novo-ampicillin Sus 250mg/5ml Ampicin for Injection 250mg Penbritin Inj 2000mg Apo Ampi Capsules 500mg Taro-ampicillin Cap 500mg AMPICILLIN and SULBACTAM Ampicillin for Injection, USP Ampicillin Sodium for Injection BP Ampicillin Penbritin-1000 Pws 1000mg/vial
Indication	For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc
Categories	Amides Aminopenicillins Anti-Bacterial Agents Anti-Infective Agents Antibacterials for Systemic Use Antiinfectives for Systemic Use Beta-Lactam Antibacterials beta-Lactams Drugs that are Mainly Renally Excreted Heterocyclic Compounds, Fused-Ring Lactams Ophthalmologicals Penicillin G Penicillins Penicillins With Extended Spectrum Sensory Organs Sulfur Compounds
ATC-Code	J01CR50 J01CA51 J01CA01 S01AA19
CAS number	69-53-4

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Penicillin-binding protein 2a	MKLDKLFEKFLSLFKKETSELEDSDSTILRRSRSDRKKLAQVGPIRKFWR...	unknown	inhibitor
Penicillin-binding protein 1b	MQNQLNELKRKMLEFFQQKQKNKKSARPGKKGSSTKKSKTLDKSAIFPAI...	unknown	inhibitor
Penicillin-binding protein 3	MKKIFLTLLTVSLLGGASTAVAQDFTIAAKHAIAVEANTGKILYEKDATQ...	unknown	inhibitor
Penicillin-binding protein 1A	MNKPTILRLIKYLSISFLSLVIAAIVLGGGVFFYYVSKAPSLSESKLVAT...	unknown	inhibitor
Penicillin-binding protein 2B	MRKFNSHSIPIRLNLLFSIVILLFMTIIGRLLYMQVLNKDFYEKKLASAS...	unknown	inhibitor
Solute carrier family 15 member 1	MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...	unknown
Solute carrier family 15 member 2	MNPFQKNESKETLFSPVSIEEVPPRPPSPPKKPSPTICGSNYPLSIAFIV...	unknown
Angiopoietin-1 receptor	MDSLASLVLCGVSLLLSGTVEGAMDLILINSLPLVSDAETSLTCIASGWR...	unknown
Albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	other/unknown
Organic cation/carnitine transporter 2	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	inhibitor
Solute carrier family 15 member 1	MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...	unknown	inhibitor
Solute carrier family 15 member 2	MNPFQKNESKETLFSPVSIEEVPPRPPSPPKKPSPTICGSNYPLSIAFIV...	unknown	inhibitor
Monocarboxylate transporter 1	MPPAVGGPVGYTPPDGGWGWAVVIGAFISIGFSYAFPKSITVFFKEIEGI...	unknown
View More

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682