7-Aminocephalosporanic acid

Details

• Internal ID: d5db8d53-dea3-4500-a90e-181844dcd469
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives
• IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• InChI: InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1
• InChI Key: HSHGZXNAXBPPDL-HZGVNTEJSA-N
• Popularity: 517 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂N₂O₅S
• Molecular Weight: 272.28 g/mol
• Exact Mass: 272.04669266 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: -4.00
• Atomic LogP (AlogP): -0.87
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 957-68-6
• 7-ACA
• 7-Aminocephalosporinic acid
• 7-ACS
• (7R)-7-aminocephalosporanic acid
• 7beta-Aminocephalosporanic acid
• Cephalosporanic acid, 7-amino
• CHEBI:2255
• (6R,7R)-3-(acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 7-amino cephalosporanic acid
• (7R)-7-Aminocephalosporanate
• (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• DTXSID9045342
• 9XI67897RG
• DTXCID7025342
• 3-(ACETOXYMETHYL)-7-AMINOCEPHEM-4-CARBOXYLIC ACID
• MFCD00005177
• (6R,7R)-3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (7-ACA)
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, (6R,7R)-
• CHEMBL1615585
• UNII-9XI67897RG
• NCGC00016552-01
• (6R,7R)-3-((ACETYLOXY)METHYL)-7-AMINO-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
• 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-AMINO-8-OXO-, (6R,7R)-
• CAS-957-68-6
• Prestwick_714
• EINECS 213-485-0
• (6R)-3-(acetoxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Prestwick0_000424
• Prestwick1_000424
• Prestwick2_000424
• Prestwick3_000424
• Epitope ID:120362
• 7-Aminocephalosporanic-acid
• EC 213-485-0
• SCHEMBL78638
• BSPBio_000408
• Aminocephalosporanic acid, 7-
• SPBio_002347
• BPBio1_000450
• 7beta-amino-cephalosporanic acid
• 7-Aminocephalosporanic Acid,(S)
• HSHGZXNAXBPPDL-HZGVNTEJSA-N
• 7-Aminocephalosporanic acid, 98%
• HMS1569E10
• HMS2096E10
• HMS3713E10
• (7R)-7-amino-cephalosporanic acid
• AMY24080
• BCP22888
• HY-B1434
• 7-AMINO-CEPHALOSPORANIC ACID
• Tox21_110490
• s2530
• AKOS015951379
• Tox21_110490_1
• CCG-220424
• CS-4823
• SMP2_000203
• 7-AMINOCEPHALOSPORANIC ACID [MI]
• 7.BETA.-AMINOCEPHALOSPORANIC ACID
• NCGC00179570-01
• NCGC00179570-03
• NCGC00263474-01
• AC-24181
• AS-15727
• CEFTRIAXONE SODIUM IMPURITY E [IP]
• (6R,7R)-3-(acetoxymethyl)-7-amino-8-
• 7-AMINOCEPHALOSPORANIC ACID [WHO-DD]
• oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-
• A-5300
• C07756
• EN300-130700
• CEFAZOLIN SODIUM IMPURITY H [EP IMPURITY]
• CEFOPERAZONE SODIUM IMPURITY E [EP IMPURITY]
• Q4642864
• BRD-K65377893-001-01-7
• 3-Acetoxymethyl-7beta-aminoceph-3-em-4-carboxylic acid
• 7beta-amino-3-acetoxymethyl-3-cephem-4-carboxylic acid
• Z1633053940
• 7.BETA.-AMINO-3-ACETOXYMETHYLCEPHEMCARBOXYLIC ACID
• (6R,7R)-3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid
• 3-ACETOXYMETHYL-7.BETA.-AMINOCEPH-3-EM-4-CARBOXYLIC ACID
• 3-acetoxymethyl-7beta-amino-3,4-didehydrocepham-4-carboxylic acid
• 7-Aminocephalosporanic acid, Antibiotic for Culture Media Use Only
• 3-Acetoxymethylen-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• (6R,7R)-3-(acetoxymethyl)-7-amino-8-keto-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-3-(acetyloxymethyl)-7-azanyl-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 4KR

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5117	51.17%
Caco-2	-	0.8812	88.12%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4371	43.71%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9254	92.54%
OATP1B3 inhibitior	+	0.9437	94.37%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9010	90.10%
P-glycoprotein inhibitior	-	0.9747	97.47%
P-glycoprotein substrate	-	0.8896	88.96%
CYP3A4 substrate	-	0.5369	53.69%
CYP2C9 substrate	+	0.5977	59.77%
CYP2D6 substrate	-	0.8679	86.79%
CYP3A4 inhibition	-	0.8568	85.68%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8943	89.43%
CYP inhibitory promiscuity	-	0.9053	90.53%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5925	59.25%
Eye corrosion	-	0.9868	98.68%
Eye irritation	+	0.6284	62.84%
Skin irritation	-	0.7423	74.23%
Skin corrosion	-	0.9228	92.28%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7487	74.87%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.7578	75.78%
skin sensitisation	-	0.8834	88.34%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.8430	84.30%
Acute Oral Toxicity (c)	IV	0.5918	59.18%
Estrogen receptor binding	-	0.6525	65.25%
Androgen receptor binding	-	0.7007	70.07%
Thyroid receptor binding	-	0.6682	66.82%
Glucocorticoid receptor binding	-	0.4884	48.84%
Aromatase binding	-	0.7580	75.80%
PPAR gamma	+	0.6080	60.80%
Honey bee toxicity	-	0.8942	89.42%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7750	77.50%
Fish aquatic toxicity	+	0.8527	85.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	316.2 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	98.92%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	94.78%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.87%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.32%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.17%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.12%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	83.21%	91.19%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.13%	94.42%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 441328
• LOTUS: LTS0003924
• wikiData: Q96621116