Limacine

Details

• Internal ID: 26220c50-ddc6-43e0-9ca7-e28cbd96e63a
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (1R,14R)-9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaen-21-ol
• SMILES (Canonical): CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)O)OC)OC
• SMILES (Isomeric): CN1CCC2=CC(=C3C=C2[C@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@@H]6C7=C(O3)C(=C(C=C7CCN6C)OC)O)OC)OC
• InChI: InChI=1S/C37H40N2O6/c1-38-14-12-24-19-31(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)41-3)17-29-35-25(13-15-39(29)2)20-34(43-5)36(40)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29-/m1/s1
• InChI Key: IIQSJHUEZBTSAT-FQLXRVMXSA-N
• Popularity: 103 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₀N₂O₆
• Molecular Weight: 608.70 g/mol
• Exact Mass: 608.28863700 g/mol
• Topological Polar Surface Area (TPSA): 72.90 Ų
• XlogP: 6.10
• Atomic LogP (AlogP): 6.86
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• CHEMBL509803
• (1R,14R)-9,20,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaen-21-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8474	84.74%
Caco-2	+	0.6626	66.26%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4795	47.95%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9264	92.64%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9950	99.50%
P-glycoprotein inhibitior	+	0.9326	93.26%
P-glycoprotein substrate	+	0.6478	64.78%
CYP3A4 substrate	+	0.6726	67.26%
CYP2C9 substrate	+	0.7890	78.90%
CYP2D6 substrate	+	0.7253	72.53%
CYP3A4 inhibition	-	0.8481	84.81%
CYP2C9 inhibition	-	0.9517	95.17%
CYP2C19 inhibition	-	0.9248	92.48%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9157	91.57%
CYP2C8 inhibition	+	0.5764	57.64%
CYP inhibitory promiscuity	-	0.9706	97.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6360	63.60%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9395	93.95%
Skin irritation	-	0.7831	78.31%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8946	89.46%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.9500	95.00%
skin sensitisation	-	0.8898	88.98%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8937	89.37%
Acute Oral Toxicity (c)	III	0.7616	76.16%
Estrogen receptor binding	+	0.7502	75.02%
Androgen receptor binding	+	0.7261	72.61%
Thyroid receptor binding	+	0.6818	68.18%
Glucocorticoid receptor binding	+	0.8691	86.91%
Aromatase binding	+	0.6301	63.01%
PPAR gamma	+	0.6050	60.50%
Honey bee toxicity	-	0.7623	76.23%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.7947	79.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.54%	96.09%
CHEMBL2056	P21728	Dopamine D1 receptor	95.15%	91.00%
CHEMBL217	P14416	Dopamine D2 receptor	95.07%	95.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.39%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.96%	93.99%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.21%	89.62%
CHEMBL2581	P07339	Cathepsin D	90.80%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.34%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.30%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.95%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.81%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.50%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.04%	82.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.65%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.19%	93.40%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.06%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.94%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.44%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.25%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.95%	94.00%
CHEMBL4208	P20618	Proteasome component C5	83.56%	90.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.38%	90.95%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.31%	100.00%
CHEMBL2535	P11166	Glucose transporter	83.07%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.89%	89.50%

Plants that contains it

• Abuta grandifolia
• Anisocycla jollyana
• Arcangelisia flava
• Caryomene olivascens
• Cyclea barbata
• Gyrocarpus americanus
• Hypserpa nitida
• Magnolia ovata
• Pycnarrhena longifolia
• Spirospermum penduliflorum

Cross-Links

• PubChem: 7656034
• NPASS: NPC182052
• ChEMBL: CHEMBL509803
• LOTUS: LTS0146090
• wikiData: Q104403741