N-methyl-N-[(10S,12S,16R)-3,5,14-trimethoxy-13-oxo-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10-tetracyclo[9.5.0.02,7.012,16]hexadeca-1(11),2,4,6,14-pentaenyl]acetamide

Details

• Internal ID: 6adb6460-795b-4f9f-a070-2270877bfb83
• Taxonomy: Alkaloids and derivatives > Lumicolchicine alkaloids
• IUPAC Name: N-methyl-N-[(10S,12S,16R)-3,5,14-trimethoxy-13-oxo-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10-tetracyclo[9.5.0.02,7.012,16]hexadeca-1(11),2,4,6,14-pentaenyl]acetamide
• SMILES (Canonical): CC(=O)N(C)C1CCC2=CC(=C(C(=C2C3=C1C4C3C=C(C4=O)OC)OC)OC5C(C(C(C(O5)CO)O)O)O)OC
• SMILES (Isomeric): CC(=O)N(C)[C@H]1CCC2=CC(=C(C(=C2C3=C1[C@@H]4[C@H]3C=C(C4=O)OC)OC)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC
• InChI: InChI=1S/C28H35NO11/c1-11(31)29(2)14-7-6-12-8-16(37-4)26(40-28-25(35)24(34)23(33)17(10-30)39-28)27(38-5)18(12)19-13-9-15(36-3)22(32)20(13)21(14)19/h8-9,13-14,17,20,23-25,28,30,33-35H,6-7,10H2,1-5H3/t13-,14-,17+,20-,23+,24-,25+,28-/m0/s1
• InChI Key: USTNADWJYOCTQA-VSOSOMBCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₅NO₁₁
• Molecular Weight: 561.60 g/mol
• Exact Mass: 561.22101093 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.21
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5907	59.07%
Caco-2	-	0.7838	78.38%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Nucleus	0.5761	57.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8652	86.52%
OATP1B3 inhibitior	+	0.9290	92.90%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9348	93.48%
P-glycoprotein inhibitior	+	0.5877	58.77%
P-glycoprotein substrate	-	0.5249	52.49%
CYP3A4 substrate	+	0.7004	70.04%
CYP2C9 substrate	-	0.6043	60.43%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	-	0.8390	83.90%
CYP2C9 inhibition	-	0.7795	77.95%
CYP2C19 inhibition	-	0.7981	79.81%
CYP2D6 inhibition	-	0.8791	87.91%
CYP1A2 inhibition	-	0.7950	79.50%
CYP2C8 inhibition	+	0.6046	60.46%
CYP inhibitory promiscuity	-	0.7596	75.96%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6088	60.88%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9414	94.14%
Skin irritation	-	0.7593	75.93%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4249	42.49%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.5592	55.92%
skin sensitisation	-	0.8568	85.68%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.5541	55.41%
Acute Oral Toxicity (c)	III	0.6141	61.41%
Estrogen receptor binding	+	0.7960	79.60%
Androgen receptor binding	+	0.6793	67.93%
Thyroid receptor binding	-	0.5257	52.57%
Glucocorticoid receptor binding	+	0.6134	61.34%
Aromatase binding	-	0.5051	50.51%
PPAR gamma	+	0.6441	64.41%
Honey bee toxicity	-	0.7582	75.82%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6849	68.49%
Fish aquatic toxicity	+	0.8758	87.58%

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	98.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.16%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.50%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.22%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	93.50%	95.89%
CHEMBL2581	P07339	Cathepsin D	93.39%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.68%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.48%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.31%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.99%	96.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.14%	94.00%
CHEMBL2535	P11166	Glucose transporter	86.79%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.28%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.20%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.73%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.60%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.46%	92.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.90%	92.94%
CHEMBL4208	P20618	Proteasome component C5	81.05%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.96%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	80.21%	91.19%

Plants that contains it

• Colchicum autumnale

Cross-Links

• PubChem: 162877239
• LOTUS: LTS0255588
• wikiData: Q105278509