Oleandomycin

Details

• Internal ID: e285a326-9199-4f3e-93c9-1502f7b6a921
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides
• IUPAC Name: (3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione
• SMILES (Canonical): CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
• InChI: InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1
• InChI Key: RZPAKFUAFGMUPI-QESOVKLGSA-N
• Popularity: 1,079 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₆₁NO₁₂
• Molecular Weight: 687.90 g/mol
• Exact Mass: 687.41937638 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.91
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• Amimycin
• Landomycin
• Matromycin
• Romicil
• 3922-90-5
• Oleandomycin [INN]
• Oleandomicina
• Oleandomycine
• Oleandomycinum
• Oleandomycin A
• Oleandomycin [INN:BAN]
• UNII-P8ZQ646136
• CHEBI:16869
• P8ZQ646136
• Antibiotic PA-105
• Oleandomycine [French]
• PA 775
• Oleandomycine [INN-French]
• Oleandomycinum [INN-Latin]
• Oleandomicina [INN-Spanish]
• HSDB 7442
• EINECS 223-495-7
• AI3-50163
• Oleandomycin (chloroform solvate)
• C35-H61-N-O12
• 12-((2,6-Didesoxy-3-O-methyl-alpha-K-arabino-hexopyranosyl)oxy)-8-hydroxy-5,7,8,11,13,15-hexamethyl-14-((3,4,6-tridesoxy-3-dimethylamino-beta-D-xylo-hexopyranosyl)oxy)-1,9-dioxaspiro(2.13)hexadecan-4,10-dion
• Prestwick3_000152
• OLEANDOMYCIN [MI]
• OLEANDOMYCIN [HSDB]
• SCHEMBL3717
• BSPBio_000284
• OLEANDOMYCIN [WHO-DD]
• BPBio1_000314
• CHEMBL606258
• OLEANDOMYCIN [GREEN BOOK]
• RZPAKFUAFGMUPI-QESOVKLGSA-N
• BDBM234401
• LMPK04000007
• DB11442
• NCGC00179617-01
• E704
• HY-116010
• AB00513809
• CS-0063452
• Oleandomycin 1000 microg/mL in Acetonitrile
• ,11-dioxaspiro[2.13]hexadecane-10,16-dione
• C01946
• (3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-6-hydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-14-[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyloxy]-1,9-dioxaspiro[2.13]hexadec-12-yl 2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranoside
• (3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7506	75.06%
Caco-2	-	0.8501	85.01%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Lysosomes	0.4323	43.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9137	91.37%
OATP1B3 inhibitior	-	0.3286	32.86%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5418	54.18%
P-glycoprotein inhibitior	+	0.6929	69.29%
P-glycoprotein substrate	+	0.7848	78.48%
CYP3A4 substrate	+	0.7413	74.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8629	86.29%
CYP3A4 inhibition	-	0.5537	55.37%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9291	92.91%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9464	94.64%
CYP inhibitory promiscuity	-	0.9629	96.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5365	53.65%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9131	91.31%
Skin irritation	-	0.7850	78.50%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.5283	52.83%
Human Ether-a-go-go-Related Gene inhibition	-	0.7261	72.61%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.8743	87.43%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.5705	57.05%
Acute Oral Toxicity (c)	IV	0.6828	68.28%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	-	0.7279	72.79%
Glucocorticoid receptor binding	+	0.6881	68.81%
Aromatase binding	+	0.6055	60.55%
PPAR gamma	+	0.6309	63.09%
Honey bee toxicity	-	0.5236	52.36%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.7190	71.90%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	1.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.54%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.99%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.83%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.69%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.23%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.69%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.56%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.09%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.95%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.73%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.53%	92.94%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.31%	94.33%
CHEMBL3572	P11597	Cholesteryl ester transfer protein	80.08%	92.67%

Plants that contains it

• Allium ampeloprasum
• Artemisia gmelinii
• Drimia altissima
• Helenium amarum
• Scutellaria viscidula
• Senecio retrorsus
• Taxus wallichiana

Cross-Links

• PubChem: 72493
• NPASS: NPC137453
• LOTUS: LTS0107627
• wikiData: Q1076248