Adicillin

Details

• Internal ID: 9dfde8f7-5f74-4019-8856-038a5fd65f1f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > N-acyl-alpha amino acids and derivatives
• IUPAC Name: (2S,5R,6R)-6-[[(5R)-5-amino-5-carboxypentanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• SMILES (Canonical): CC1(C(N2C(S1)C(C2=O)NC(=O)CCCC(C(=O)O)N)C(=O)O)C
• SMILES (Isomeric): CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CCC[C@H](C(=O)O)N)C(=O)O)C
• InChI: InChI=1S/C14H21N3O6S/c1-14(2)9(13(22)23)17-10(19)8(11(17)24-14)16-7(18)5-3-4-6(15)12(20)21/h6,8-9,11H,3-5,15H2,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t6-,8-,9+,11-/m1/s1
• InChI Key: MIFYHUACUWQUKT-GPUHXXMPSA-N
• Popularity: 123 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₁N₃O₆S
• Molecular Weight: 359.40 g/mol
• Exact Mass: 359.11510657 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -0.80
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• Penicillin N
• Cephalosporin N
• Salmotin
• Adicillinum
• 525-94-0
• Synnematin N
• Cephalosphorin R
• (4-Amino-4-carboxybutyl)penicillin
• Adicilline
• Adicilina
• Adicillin [INN:BAN]
• Adicilina [INN-Spanish]
• Adicilline [INN-French]
• Adicillinum [INN-Latin]
• SYNNEMATIN B
• UNII-NOF9U9EYQ4
• NOF9U9EYQ4
• NSC 113137
• (D-4-Amino-4-carboxybutyl) penicillinic acid
• C14H21N3O6S
• CHEBI:18203
• NSC-113137
• 6-N-((5-Amino-5-carboxy)pentanoyl)aminopenicillansaeure
• (2S,5R,6R)-6-(5-Amino-5-carboxyvaleramido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure
• 6-(5-Amino-5-carboxyvaleramido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• 6beta-[(5R)-5-amino-5-carboxypentanamido]-2,2-dimethylpenam-3alpha-carboxylic acid
• Penicillin N;Adicillin
• (2S,5R,6R)-6-[(5R)-5-amino-5-carboxypentanamido]-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-((5-amino-5-carboxy-1-oxopentyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-
• PenicillinN
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(5-amino-5-carboxyvaleramido)-3,3-dimethyl-7-oxo-, D-
• 6-(5-Amino-5-carboxyvaleramido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Adicillin [BAN:INN]
• ADICILLIN [INN]
• ADICILLIN [MART.]
• PENICILLIN N [MI]
• ADICILLIN [WHO-DD]
• SCHEMBL34373
• CHEMBL2023705
• MIFYHUACUWQUKT-GPUHXXMPSA-N
• DTXSID301023757
• LS-149716
• C06564
• Q27102898
• (2S,5R,6R)-6-[[(5R)-5-amino-5-carboxypentanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9392	93.92%
Caco-2	-	0.9400	94.00%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Lysosomes	0.5684	56.84%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.9218	92.18%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9072	90.72%
BSEP inhibitior	-	0.8532	85.32%
P-glycoprotein inhibitior	-	0.8865	88.65%
P-glycoprotein substrate	-	0.7373	73.73%
CYP3A4 substrate	+	0.5626	56.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8317	83.17%
CYP3A4 inhibition	-	0.8408	84.08%
CYP2C9 inhibition	-	0.9069	90.69%
CYP2C19 inhibition	-	0.8939	89.39%
CYP2D6 inhibition	-	0.9253	92.53%
CYP1A2 inhibition	-	0.8868	88.68%
CYP2C8 inhibition	-	0.9755	97.55%
CYP inhibitory promiscuity	-	0.9860	98.60%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7300	73.00%
Carcinogenicity (trinary)	Non-required	0.6422	64.22%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9952	99.52%
Skin irritation	-	0.7535	75.35%
Skin corrosion	-	0.9048	90.48%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7538	75.38%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.5851	58.51%
skin sensitisation	-	0.6415	64.15%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8869	88.69%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6430	64.30%
Acute Oral Toxicity (c)	IV	0.4954	49.54%
Estrogen receptor binding	-	0.6337	63.37%
Androgen receptor binding	-	0.8365	83.65%
Thyroid receptor binding	-	0.5846	58.46%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6404	64.04%
PPAR gamma	-	0.4942	49.42%
Honey bee toxicity	-	0.9233	92.33%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8300	83.00%
Fish aquatic toxicity	-	0.4808	48.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.75%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	95.61%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.76%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.72%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.14%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.80%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.11%	82.69%
CHEMBL340	P08684	Cytochrome P450 3A4	87.05%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.57%	99.23%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.72%	93.10%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.45%	94.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.22%	85.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.89%	96.47%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	83.88%	92.29%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.75%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.38%	89.50%
CHEMBL233	P35372	Mu opioid receptor	80.36%	97.93%

Plants that contains it

• Inula helenium
• Pinellia pedatisecta

Cross-Links

• PubChem: 71724
• NPASS: NPC117829
• LOTUS: LTS0153320
• wikiData: Q27102898