6-Aminopenicillanic acid

Details

• Internal ID: 31f85ea3-5f81-4795-974c-e311b873c281
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Dipeptides
• IUPAC Name: (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 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
• InChI Key: NGHVIOIJCVXTGV-ALEPSDHESA-N
• Popularity: 1,118 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₂N₂O₃S
• Molecular Weight: 216.26 g/mol
• Exact Mass: 216.05686342 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 551-16-6
• 6-Apa
• Penicin
• Penin
• 6-Aps
• Aminopenicillanic acid
• (+)-6-Aminopenicillanic acid
• (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Phenacyl 6-aminopenicillinate
• 6-Aminopenicillamine acid
• 6-aminopenicillanate
• QR0C4R7XVN
• DTXSID7046097
• CHEBI:16705
• NSC-50071
• 6-amino-2,2-dimethylpenam-3alpha-carboxylic acid
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• DTXCID5026097
• CHEBI:30938
• (2S,5R,6R)-6-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-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• 6-APA cpd
• RefChem:913830
• 208-993-4
• MFCD00005176
• AI3-52557
• 6-amino-penicillanic acid
• 6beta-aminopenicillanic acid
• (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure
• CHEMBL1236749
• SR-01000640154-1
• (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)
• EINECS 208-993-4
• UNII-QR0C4R7XVN
• NSC 50071
• Aminopenicillanic
• NCGC00160198-01
• amino penicillanic acid
• 6-aminopenicillanic-acid
• 6-aminopenici llanic acid
• bmse000312
• Epitope ID:117703
• EC 208-993-4
• SCHEMBL66332
• Flucloxacillin impurity C CRS
• SCHEMBL11586624
• 09070_FLUKA
• 6-aminopenicillinic acid (6-APA)
• HY-W013549R
• STR03060
• 6-Aminopenicillanic acid (Standard)
• Tox21_111749
• BDBM50420257
• CCG-50809
• EBC-03888
• s5035
• (+)-6-Aminopenicillanic acid, 96%
• 6-AMINOPENICILLANIC ACID [MI]
• AKOS015907713
• CS-W014265
• FA36389
• HY-W013549
• KS-5277
• s12351
• AC-11282
• CAS-551-16-6
• PD014430
• SY020533
• AMPICILLIN IMPURITY A [EP IMPURITY]
• PIPERACILLIN SODIUM IMPURITY H [EP]
• A0800
• NS00011463
• C02954
• EN300-114057
• (+)-6-Aminopenicillanic acid, analytical standard
• F057763
• SULBACTAM SODIUM IMPURITY B [EP IMPURITY]
• Amoxicillin EP Impurity A(Sulbactam EP Impurity B)
• AMOXICILLIN SODIUM IMPURITY A [EP IMPURITY]
• CLOXACILLIN SODIUM IMPURITY C [EP IMPURITY]
• Q2823234
• 6beta-amino-2,2-dimethylpenam-3alpha-carboxylic acid
• AMOXICILLIN TRIHYDRATE IMPURITY A [EP IMPURITY]
• AMPICILLIN TRIHYDRATE IMPURITY A [EP IMPURITY]
• BRD-K30284967-001-01-8
• DICLOXACILLIN SODIUM IMPURITY C [EP IMPURITY]
• BENZYLPENICILLIN SODIUM IMPURITY A [EP IMPURITY]
• PHENOXYMETHYLPENICILLIN IMPURITY C [EP IMPURITY]
• Z1269203097
• (3S,5R,6R)-6-amino-2,2-dimethylpenam-3-carboxylic acid
• BENZYLPENICILLIN POTASSIUM IMPURITY A [EP IMPURITY]
• (3S, 5R, 6R)-6-amino-2,2-dimethylpenam-3-carboxylic acid
• OXACILLIN SODIUM MONOHYDRATE IMPURITY A [EP IMPURITY]
• FLUCLOXACILLIN MAGNESIUM OCTAHYDRATE IMPURITY C [EP IMPURITY]
• FLUCLOXACILLIN SODIUM MONOHYDRATE IMPURITY C [EP IMPURITY]
• PHENOXYMETHYLPENICILLIN POTASSIUM IMPURITY C [EP IMPURITY]
• Flucloxacillin impurity C, European Pharmacopoeia (EP) Reference Standard
• PHENOXYMETHYLPENICILLIN (BENZATHINE) TETRAHYDRATE IMPURITY C [EP IMPURITY]
• (2S,5R,6R)-(+)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
• [2S-(2alpha,5alpha,6beta)]-6-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-amino-3,3-dimethyl-7-oxo-, (2S,6R)-
• 6-APA (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Penicin Penin
• rel-(2R,6S)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• X1E

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8319	83.19%
Caco-2	-	0.8773	87.73%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Lysosomes	0.5866	58.66%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9503	95.03%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9619	96.19%
P-glycoprotein inhibitior	-	0.9531	95.31%
P-glycoprotein substrate	-	0.9355	93.55%
CYP3A4 substrate	-	0.5768	57.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8375	83.75%
CYP3A4 inhibition	-	0.9093	90.93%
CYP2C9 inhibition	-	0.9137	91.37%
CYP2C19 inhibition	-	0.9056	90.56%
CYP2D6 inhibition	-	0.9314	93.14%
CYP1A2 inhibition	-	0.8906	89.06%
CYP2C8 inhibition	-	0.9877	98.77%
CYP inhibitory promiscuity	-	0.9900	99.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5100	51.00%
Carcinogenicity (trinary)	Non-required	0.6387	63.87%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.8014	80.14%
Skin irritation	-	0.7271	72.71%
Skin corrosion	-	0.9098	90.98%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7844	78.44%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.7676	76.76%
skin sensitisation	-	0.9435	94.35%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.4836	48.36%
Acute Oral Toxicity (c)	IV	0.5553	55.53%
Estrogen receptor binding	-	0.8036	80.36%
Androgen receptor binding	-	0.7088	70.88%
Thyroid receptor binding	-	0.7432	74.32%
Glucocorticoid receptor binding	-	0.7863	78.63%
Aromatase binding	-	0.8059	80.59%
PPAR gamma	-	0.5826	58.26%
Honey bee toxicity	-	0.9296	92.96%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.6978	69.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	0.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.83%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.85%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.66%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.64%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.54%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.41%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.23%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.89%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	82.70%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11082
• LOTUS: LTS0247465
• wikiData: Q2823234