Non-peptidic Macrocycle Database

MC-0088

Name
Unique ID		MC-0088
Original ID		azithromycin (Nožinić et al., 2010)
Common Name		Azithromycin
Structure Representations
InchiKey		MQTOSJVFKKJCRP-BICOPXKESA-N
Isomeric SMILES		CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
SMILES (Ring)		C1CCCCNCCCCOCCCC1
Permeability
Assay		Caco-2
Endpoint		P_app AB
Value		2.2 ± 1.3
Unit		nm/s
Standardized Value		-6.66
Molecule Descriptors
MW (Da)	749.00	NRotB	7
HBA	14	Kier Index (Φ)	15.58
HBD	5	AR	0.00
cLogP	1.90	Fsp³	0.97
TPSA (Å²)	180.08	MRS	15
Unique ID: ID for each unique molecule in this dataset; Original ID: The name or ID in original source; Standaridized value: Logarithmic values for permeability values (unit 10^-6 cm/s), original data with sign '<' or '>' were removed during data standardization
Abbreviations: MW (Da): Molecular Weight; HBA: Hydrogen bond acceptor; HBD: Hydrogen bond donor; cLogP: Calculated lipophilicity; TPSA: Topological polar surface area; NRotB: Number of rotatable bonds; Φ: Kier flexibility Index: Fsp³: fraction of sp³ carbon atoms; MRS: macrocyclic ring size; AR: Amide ratio;

Name	MW(Da)	HBA	HBD	cLogP	TPSA(Å²)	Kier Index (Φ)
MC-0088	749.00	14	5	1.90	180.08	15.58
MC-3815	749.00	14	5	1.90	180.08	15.58
MC-3816	1258.54	23	6	4.52	294.67	22.70
MC-3817	1286.59	23	6	5.30	294.67	23.84
MC-3818	1314.65	23	6	6.08	294.67	25.00
MC-3819	1370.75	23	6	7.64	294.67	27.36
MC-3820	1128.40	20	6	4.02	266.98	20.86
MC-3821	1142.42	20	6	4.41	266.98	21.43
MC-3822	791.03	15	4	2.47	186.15	16.58
MC-3823	699.93	12	5	2.12	170.49	16.26
MC-3824	830.07	15	5	2.27	198.18	17.85
MC-3825	858.12	15	5	3.05	198.18	19.12
MC-3826	900.16	16	4	3.62	204.25	20.15

Name	Assay	Endpoint	Value	Unit	Standardized Value	Source
MC-0088	Caco-2	ER	75		75.00	(Nožinić et al., 2010)
MC-0088	Caco-2	ER	11		11.00	(Rossi Sebastiano et al., 2018)
MC-0088	Caco-2	ER+Inh.	7.9		7.90	(Rossi Sebastiano et al., 2018)
MC-0088	MDCK	ER	4.2		4.20	(Nožinić et al., 2010)
MC-0088	MDCK	ER+Inh.	1.3		1.30	(Nožinić et al., 2010)
MC-0088	Caco-2	ER+Inh.	1		1.00	(Nožinić et al., 2010)
MC-0088	Caco-2	Papp BA+Inh.	22.5	10^-6 cm/s	-4.65	(Rossi Sebastiano et al., 2018)
MC-0088	Caco-2	Papp BA	19.8	10^-6 cm/s	-4.70	(Rossi Sebastiano et al., 2018)
MC-0088	Caco-2	Papp BA	166.4 ± 13.1	nm/s	-4.78	(Nožinić et al., 2010)
MC-0088	MDCK	Papp BA	109.7 ± 18.7	nm/s	-4.96	(Nožinić et al., 2010)
MC-0088	MDCK	Papp BA+Inh.	48.2±9.9	nm/s	-5.32	(Nožinić et al., 2010)
MC-0088	MDCK	Papp AB+Inh.	35.9±0.1	nm/s	-5.44	(Nožinić et al., 2010)
MC-0088	Caco-2	Papp AB+Inh.	2.8	10^-6 cm/s	-5.55	(Rossi Sebastiano et al., 2018)
MC-0088	MDCK	Papp AB	25.9 ± 4.3	nm/s	-5.59	(Nožinić et al., 2010)
MC-0088	Caco-2	Papp AB	1.8	10^-6 cm/s	-5.74	(Rossi Sebastiano et al., 2018)
MC-0088	Caco-2	Papp AB+Inh.	16.8±4.3	nm/s	-5.78	(Nožinić et al., 2010)
MC-0088	Caco-2	Papp BA+Inh.	16.5±3.3	nm/s	-5.78	(Nožinić et al., 2010)
MC-0088	PAMPA	Papp	10.1±0.9	nm/s	-6.00	(Nožinić et al., 2010)
MC-0088	Caco-2	Papp	1	10^-6 cm/s	-6.00	(Naylor et al., 2018)

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