Molecule

Adicillin

AlkaPlorer ID: AK018292

Synonym: None

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

Structure

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

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

InChIKey: MIFYHUACUWQUKT-GPUHXXMPSA-N

Reference

Purification and properties of isopenicillin N epimerase from Streptomyces clavuligerus

PubChem CID: 71724

CAS: 525-94-0

LOTUS: LTS0153320

SuperNatural Ⅲ: SN0226398-05

NPASS: NPC117829

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Teucrium kotschyanum	Teucrium	Lamiaceae	Lamiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Phyla canescens	Phyla	Verbenaceae	Lamiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Bauhinia forficata	Bauhinia	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Pinellia pedatisecta	Pinellia	Araceae	Alismatales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Polyporus arcularius	Polyporus	Polyporaceae	Polyporales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Acipenser sturio	Acipenser	Acipenseridae	Acipenseriformes	Actinopteri	Chordata	Metazoa	Eukaryota
Senecio leptolobus	Senecio	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Inula helenium	Inula	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Pterogorgia citrina	Pterogorgia	Pterogorgiidae	Malacalcyonacea	Anthozoa	Cnidaria	Metazoa	Eukaryota
Nymania capensis	Nymania	Meliaceae	Sapindales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Prunus nipponica	Prunus	Rosaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Abies grandis	Abies	Pinaceae	Pinales	Pinopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 359.40400000000005

TPSA？: 153.52

MolLogP？: 0.040600000000002

Number of H-Donors: 4

Number of H-Acceptors: 6

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Escherichia coli	Escherichia coli	MIC	8.0	ug.mL-1	10.1016/j.ejmech.2012.03.008
Homo sapiens	A498	GI50	44668.36	nM	None
Homo sapiens	A549	GI50	50003.45	nM	None
Homo sapiens	CAKI-1	GI50	50003.45	nM	None
Homo sapiens	CCRF-CEM	GI50	50003.45	nM	None
Homo sapiens	COLO 205	GI50	50003.45	nM	None
Homo sapiens	DLD-1	GI50	50003.45	nM	None
Homo sapiens	DMS-114	GI50	50003.45	nM	None
Homo sapiens	DMS-273	GI50	50003.45	nM	None
Homo sapiens	EKVX	GI50	50003.45	nM	None
Homo sapiens	HCC 2998	GI50	50003.45	nM	None
Homo sapiens	HCT-116	GI50	50003.45	nM	None
Homo sapiens	HCT-15	GI50	50003.45	nM	None
Homo sapiens	HL-60	GI50	50003.45	nM	None
Homo sapiens	HOP-18	GI50	50003.45	nM	None
Homo sapiens	HOP-62	GI50	50003.45	nM	None
Homo sapiens	HOP-92	GI50	50003.45	nM	None
Homo sapiens	HT-29	GI50	50003.45	nM	None
Homo sapiens	IGROV-1	GI50	50003.45	nM	None
Homo sapiens	K562	GI50	50003.45	nM	None
Homo sapiens	KM12	GI50	50003.45	nM	None
Homo sapiens	KM-20L2	GI50	24774.22	nM	None
Homo sapiens	LOX IMVI	GI50	50003.45	nM	None
Homo sapiens	M19-MEL	GI50	50003.45	nM	None
Homo sapiens	Malme-3M	GI50	50003.45	nM	None
Homo sapiens	MCF7	GI50	50003.45	nM	None
Homo sapiens	MOLT-4	GI50	50003.45	nM	None
Homo sapiens	NCI/ADR-RES	GI50	31550.05	nM	None
Homo sapiens	NCI-H226	GI50	50003.45	nM	None
Homo sapiens	NCI-H23	GI50	50003.45	nM	None
Homo sapiens	NCI-H322M	GI50	50003.45	nM	None
Homo sapiens	NCI-H460	GI50	50003.45	nM	None
Homo sapiens	NCI-H522	GI50	50003.45	nM	None
Homo sapiens	OVCAR-3	GI50	50003.45	nM	None
Homo sapiens	OVCAR-4	GI50	50003.45	nM	None
Homo sapiens	OVCAR-5	GI50	23280.91	nM	None
Homo sapiens	OVCAR-8	GI50	19906.73	nM	None
Homo sapiens	RPMI-8226	GI50	50003.45	nM	None
Homo sapiens	RXF 393	GI50	50003.45	nM	None
Homo sapiens	SF-268	GI50	50003.45	nM	None
Homo sapiens	SF-295	GI50	50003.45	nM	None
Homo sapiens	SF-539	GI50	50003.45	nM	None
Homo sapiens	SK-MEL-2	GI50	50003.45	nM	None
Homo sapiens	SK-MEL-28	GI50	50003.45	nM	None
Homo sapiens	SK-MEL-5	GI50	15031.42	nM	None
Homo sapiens	SK-OV-3	GI50	41020.41	nM	None
Homo sapiens	SN12C	GI50	50003.45	nM	None
Homo sapiens	SN12K1	GI50	50003.45	nM	None
Homo sapiens	SNB-19	GI50	50003.45	nM	None
Homo sapiens	SNB-75	GI50	50003.45	nM	None
Homo sapiens	SNB-78	GI50	50003.45	nM	None
Homo sapiens	SW-620	GI50	31550.05	nM	None
Homo sapiens	U-251	GI50	25585.86	nM	None
Homo sapiens	UACC-257	GI50	50003.45	nM	None
Homo sapiens	UACC-62	GI50	50003.45	nM	None
Homo sapiens	UO-31	GI50	50003.45	nM	None
Homo sapiens	XF498	GI50	24099.05	nM	None
Mus musculus	P388	GI50	50003.45	nM	None
Mus musculus	P388/ADR	GI50	50003.45	nM	None
Salmonella enterica subsp. enterica serovar Typhimurium	Salmonella typhimurium	Ratio	1.0	None	10.1016/j.ejmech.2012.03.008
None	Unchecked	k cat	0.442	s-1	10.1016/S0960-894X(96)00278-8
None	Unchecked	Km	10340000.0	nM	10.1016/S0960-894X(96)00278-8

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT006870	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.O=C(O)CCC(=O)C(=O)O>>CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1.O=C(O)CCC(=O)O.O=C=O	None
AKRT006871	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]([C@H](NC(=O)CCC[C@@H](N)C(=O)O)C(=O)O)N[C@H]1C(=O)O	enzymemap_78677
AKRT006872	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(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1	1.14.20.1-RXN
AKRT006877	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](NC(=O)CCC[C@@H](N)C(=O)O)C(=O)N2[C@H]1C(=O)O	5.1.1.17-RXN
AKRT020256	N[C@H](CCCC(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CO)CS[C@H]12)C(=O)O>>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	MNXR134529