17-Methylenespiramycin

Details

• Internal ID: 4cfd95d6-7463-4b0d-b045-be8976bdd141
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides
• IUPAC Name: 2-[(5S,6S,7R,9R,11Z,13Z,16R)-6-[5-(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]prop-2-enal
• SMILES (Canonical): CC1CC=CC=CC(C(CC(C(C(C(CC(=O)O1)O)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)C(=C)C=O)C)OC4CCC(C(O4)C)N(C)C
• SMILES (Isomeric): C[C@@H]1C/C=C\C=C/C([C@@H](C[C@@H]([C@@H]([C@H](C(CC(=O)O1)O)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)C(=C)C=O)C)OC4CCC(C(O4)C)N(C)C
• InChI: InChI=1S/C44H74N2O14/c1-24-20-30(25(2)23-47)40(60-43-38(50)37(46(10)11)39(28(5)57-43)59-36-22-44(7,52)42(51)29(6)56-36)41(53-12)32(48)21-34(49)54-26(3)16-14-13-15-17-33(24)58-35-19-18-31(45(8)9)27(4)55-35/h13-15,17,23-24,26-33,35-43,48,50-52H,2,16,18-22H2,1,3-12H3/b14-13-,17-15-/t24-,26-,27?,28?,29?,30-,31?,32?,33?,35?,36?,37?,38?,39?,40+,41+,42?,43?,44?/m1/s1
• InChI Key: SPUCVXIQVCUVAK-BUOLHCRLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₄N₂O₁₄
• Molecular Weight: 855.10 g/mol
• Exact Mass: 854.51400504 g/mol
• Topological Polar Surface Area (TPSA): 195.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.49
• H-Bond Acceptor: 16
• H-Bond Donor: 4
• Rotatable Bonds: 11

Synonyms

• 2-[(5S,6S,7R,9R,11Z,13Z,16R)-6-[5-(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]prop-2-enal
• 2-((5S,6S,7R,9R,11Z,13Z,16R)-6-(5-(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy-10-(5-(dimethylamino)-6-methyloxan-2-yl)oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl)prop-2-enal
• RefChem:79241
• CHEBI:220633

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6648	66.48%
Caco-2	-	0.8646	86.46%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.5909	59.09%
OATP2B1 inhibitior	-	0.8666	86.66%
OATP1B1 inhibitior	+	0.8990	89.90%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9479	94.79%
P-glycoprotein inhibitior	+	0.7472	74.72%
P-glycoprotein substrate	+	0.7716	77.16%
CYP3A4 substrate	+	0.7105	71.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8841	88.41%
CYP3A4 inhibition	-	0.8373	83.73%
CYP2C9 inhibition	-	0.8654	86.54%
CYP2C19 inhibition	-	0.8481	84.81%
CYP2D6 inhibition	-	0.9225	92.25%
CYP1A2 inhibition	-	0.8796	87.96%
CYP2C8 inhibition	+	0.6105	61.05%
CYP inhibitory promiscuity	-	0.9854	98.54%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5092	50.92%
Eye corrosion	-	0.9828	98.28%
Eye irritation	-	0.9118	91.18%
Skin irritation	-	0.7334	73.34%
Skin corrosion	-	0.9096	90.96%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7077	70.77%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.6497	64.97%
skin sensitisation	-	0.8423	84.23%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7490	74.90%
Acute Oral Toxicity (c)	III	0.5061	50.61%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.6847	68.47%
Thyroid receptor binding	+	0.5648	56.48%
Glucocorticoid receptor binding	+	0.7300	73.00%
Aromatase binding	-	0.6187	61.87%
PPAR gamma	+	0.7861	78.61%
Honey bee toxicity	-	0.5307	53.07%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.7800	78.00%
Fish aquatic toxicity	+	0.8668	86.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.79%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.62%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.86%	96.09%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	94.66%	91.83%
CHEMBL2581	P07339	Cathepsin D	93.47%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.31%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.03%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	89.65%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.22%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.87%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.21%	95.89%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	88.12%	86.00%
CHEMBL1902	P62942	FK506-binding protein 1A	87.84%	97.05%
CHEMBL4208	P20618	Proteasome component C5	87.57%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.70%	99.23%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	85.84%	98.99%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.72%	92.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.56%	93.56%
CHEMBL1951	P21397	Monoamine oxidase A	85.35%	91.49%
CHEMBL2664	P23526	Adenosylhomocysteinase	84.79%	86.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.29%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.18%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.96%	97.36%
CHEMBL1871	P10275	Androgen Receptor	81.47%	96.43%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.45%	91.24%

Plants that contains it

• Ajuga decumbens

Cross-Links

• PubChem: 139586349
• LOTUS: LTS0159236
• wikiData: Q105364943