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6-aminopenicillanic acid

AlkaPlorer ID: AK027760

Synonym: None

IUPAC Name: (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Structure

SMILES: CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O

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InChI: InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1

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InChIKey: NGHVIOIJCVXTGV-ALEPSDHESA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Emericellopsis minima Emericellopsis None Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 216.262

TPSA？: 83.63000000000001

MolLogP？: -0.5393999999999992

Number of H-Donors: 2

Number of H-Acceptors: 4

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 14125.4 nM None
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 14091.9 nM None
Homo sapiens Histone deacetylase 6 Inhibition -5.79 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -3.16 % 10.6019/CHEMBL4808148
Homo sapiens Oligopeptide transporter small intestine isoform Ki 30000000.0 nM 10.1016/j.ejpb.2004.07.008
Homo sapiens Solute carrier family 22 member 8 Inhibition nan % 10.1124/dmd.112.049569
Klebsiella pneumoniae Klebsiella pneumoniae Activity 68.9 % 10.1016/j.ejmech.2017.06.065
Klebsiella pneumoniae Klebsiella pneumoniae MBIC 35.0 ug ml-1 10.1016/j.ejmech.2017.06.065
Klebsiella pneumoniae Klebsiella pneumoniae MIC 35.0 ug.mL-1 10.1016/j.ejmech.2017.06.065
Mus musculus Solute carrier family 22 member 6 Inhibition nan % 10.1124/dmd.112.049569
Mus musculus Solute carrier family 22 member 8 Inhibition nan % 10.1124/dmd.112.049569
Mus musculus Solute carrier family 22 member 8 PPB nan % 10.1124/dmd.112.049569
Plasmodium falciparum Plasmodium falciparum Potency 510.3 nM None
Proteus mirabilis Proteus mirabilis Activity 89.2 % 10.1016/j.ejmech.2017.06.065
Proteus mirabilis Proteus mirabilis MBIC 35.0 ug ml-1 10.1016/j.ejmech.2017.06.065
Proteus mirabilis Proteus mirabilis MIC 35.0 ug.mL-1 10.1016/j.ejmech.2017.06.065
Rattus norvegicus Oligopeptide transporter, kidney isoform Ki 19000000.0 nM 10.1016/j.ejpb.2004.07.008
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 5.813 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -4.43 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.0 % 10.6019/CHEMBL4495565
Staphylococcus aureus MecA IC50 7000000.0 nM 10.1016/j.ejmech.2020.112312
Staphylococcus aureus Staphylococcus aureus Activity 60.46 % 10.1016/j.ejmech.2017.06.065
Staphylococcus aureus Staphylococcus aureus MBIC 150.0 ug ml-1 10.1016/j.ejmech.2017.06.065
Staphylococcus aureus Staphylococcus aureus MIC 135.0 ug.mL-1 10.1016/j.ejmech.2017.06.065
Streptococcus mutans Streptococcus mutans Activity 29.31 % 10.1016/j.ejmech.2017.06.065
Streptococcus mutans Streptococcus mutans MBIC 7.0 ug ml-1 10.1016/j.ejmech.2017.06.065
Streptococcus mutans Streptococcus mutans MIC 70.0 ug.mL-1 10.1016/j.ejmech.2017.06.065
None NON-PROTEIN TARGET Activity nan None 10.1016/j.bmc.2019.04.002
None No relevant target Activity nan None 10.1016/j.bmc.2019.04.002
None No relevant target pKa 2.3 None 10.1007/s11095-013-1232-z

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000267 *C(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O R02170
AKRT000268 *C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O PENICILLIN-AMIDASE-RXN
AKRT006676 CC/C=C/CC(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O enzymemap_76068
AKRT006677 CC/C=C/CC(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O>>CC/C=C/CC(=O)O.CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O None
AKRT006856 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.COC(=O)C(N)c1ccccc1>>CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O.CO None
AKRT006857 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.NC(=O)[C@H](N)c1ccc(O)cc1>>CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O enzymemap_76181
AKRT006858 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.NC(=O)[C@H](N)c1ccccc1>>CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O enzymemap_76182
AKRT006859 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.N[C@@H](C(=O)O)c1ccccc1>>CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O enzymemap_76063
AKRT006860 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.O=C(O)CNC(=O)Cc1ccccc1>>CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O enzymemap_76133
AKRT006861 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.O=C(O)COc1ccccc1>>CC1(C)S[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N2[C@H]1C(=O)O enzymemap_76099
AKRT006862 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.O=C(O)Cc1ccccc1>>CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O enzymemap_76104
AKRT006863 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.O=C([CoA])Cc1ccccc1>>CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O RXN-17062
AKRT006864 CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.O=CO>>*C(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12 MNXR102482
AKRT006865 CC1(C)S[C@@H]2[C@H](NC(=O)C(C(=O)O)c3ccccc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O enzymemap_76117
AKRT006866 CC1(C)S[C@@H]2[C@H](NC(=O)C(C(=O)O)c3ccccc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.O=C(O)C(C(=O)O)c1ccccc1 None
AKRT006868 CC1(C)S[C@@H]2[C@H](NC(=O)CCCCC(=O)O)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O enzymemap_78202
AKRT006869 CC1(C)S[C@@H]2[C@H](NC(=O)CCCCC(=O)O)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.O=C(O)CCCCC(=O)O None
AKRT006876 CC1(C)S[C@@H]2[C@H](NC(=O)CCC[C@H](N)C(=O)O)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O RXN-17061
AKRT006879 CC1(C)S[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O enzymemap_76053
AKRT006880 CC1(C)S[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.O=C(O)COc1ccccc1 None
AKRT006882 CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O enzymemap_76125
AKRT006886 CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O MNXR145936
AKRT006887 CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.O=C(O)Cc1ccccc1 None
AKRT006891 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O MNXR133717
AKRT006892 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.NC(=O)[C@H](N)c1ccc(O)cc1 None
AKRT006898 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O MNXR129390
AKRT006899 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.NC(=O)[C@H](N)c1ccccc1 None
AKRT006900 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.N[C@@H](C(=O)O)c1ccccc1 None
AKRT007897 CCCCCC(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O enzymemap_76067
AKRT007898 CCCCCC(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.CCCCCC(=O)O None
AKRT007910 CCCCCC(=O)OC.CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O>>CCCCCC(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12 enzymemap_76097
AKRT008089 CCCCCCCC(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O enzymemap_76057
AKRT008090 CCCCCCCC(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O>>CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O.CCCCCCCC(=O)O None
AKRT008107 CCCCCCCC(=O)OC.CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O>>CCCCCCCC(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12 enzymemap_76098
AKRT010985 COC(=O)C(N)c1ccc(O)cc1.CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O enzymemap_76172
AKRT010986 COC(=O)C(N)c1ccccc1.CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O enzymemap_76107
AKRT011131 COC(=O)[C@H](N)c1ccccc1.CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O>>CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O enzymemap_76136