Insularine

Details

• Internal ID: fe8733ee-0f65-4f0c-82d7-fc32383f81f1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Ethers > Diarylethers
• IUPAC Name: (1R,16R)-9,10,26-trimethoxy-15,31-dimethyl-7,24,34-trioxa-15,31-diazaoctacyclo[19.10.3.23,6.18,12.118,22.025,33.028,32.016,36]octatriaconta-3(38),4,6(37),8(36),9,11,18(35),19,21,25,27,32-dodecaene
• SMILES (Canonical): CN1CCC2=CC(=C3C4=C2C1CC5=CC=C(C=C5)OC6=C7C(CC8=CC(=C(O4)C=C8)CO3)N(CCC7=CC(=C6OC)OC)C)OC
• SMILES (Isomeric): CN1CCC2=CC(=C3C4=C2[C@H]1CC5=CC=C(C=C5)OC6=C7[C@@H](CC8=CC(=C(O4)C=C8)CO3)N(CCC7=CC(=C6OC)OC)C)OC
• InChI: InChI=1S/C38H40N2O6/c1-39-14-13-25-20-32(42-4)36-38-34(25)28(39)17-22-6-9-27(10-7-22)45-37-33-24(19-31(41-3)35(37)43-5)12-15-40(2)29(33)18-23-8-11-30(46-38)26(16-23)21-44-36/h6-11,16,19-20,28-29H,12-15,17-18,21H2,1-5H3/t28-,29-/m1/s1
• InChI Key: DPLLCJFNXPKFPB-FQLXRVMXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₀N₂O₆
• Molecular Weight: 620.70 g/mol
• Exact Mass: 620.28863700 g/mol
• Topological Polar Surface Area (TPSA): 61.90 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 7.05
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• Insularine [MI]
• O-Methylinsulanoline
• UNII-60I96OKL0W
• 60I96OKL0W
• 549-07-5
• 6,9-(Epoxymethano)-8,11:20,23-dietheno-1H,12H-(1,10)dioxacyclooctadecino(2,3,4-ij:11,12,13-i'j')diisoquinoline, 2,3,12a,13,14,15,24,24a-octahydro-5,17,18-trimethoxy-1,13-dimethyl-, (12aR,24aR)-
• Q27263227

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9212	92.12%
Caco-2	+	0.5856	58.56%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.5053	50.53%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.9332	93.32%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9931	99.31%
P-glycoprotein inhibitior	+	0.9459	94.59%
P-glycoprotein substrate	+	0.6100	61.00%
CYP3A4 substrate	+	0.6491	64.91%
CYP2C9 substrate	+	0.7865	78.65%
CYP2D6 substrate	+	0.7650	76.50%
CYP3A4 inhibition	-	0.6195	61.95%
CYP2C9 inhibition	-	0.9207	92.07%
CYP2C19 inhibition	-	0.9058	90.58%
CYP2D6 inhibition	-	0.9061	90.61%
CYP1A2 inhibition	-	0.9118	91.18%
CYP2C8 inhibition	+	0.4585	45.85%
CYP inhibitory promiscuity	-	0.9294	92.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6200	62.00%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9468	94.68%
Skin irritation	-	0.7977	79.77%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9583	95.83%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8811	88.11%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7862	78.62%
Acute Oral Toxicity (c)	III	0.7571	75.71%
Estrogen receptor binding	+	0.5672	56.72%
Androgen receptor binding	+	0.7596	75.96%
Thyroid receptor binding	+	0.5482	54.82%
Glucocorticoid receptor binding	+	0.8310	83.10%
Aromatase binding	+	0.5914	59.14%
PPAR gamma	-	0.4943	49.43%
Honey bee toxicity	-	0.7261	72.61%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.8453	84.53%

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	99.09%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.89%	85.14%
CHEMBL2056	P21728	Dopamine D1 receptor	91.48%	91.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.35%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.34%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.01%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.70%	94.45%
CHEMBL217	P14416	Dopamine D2 receptor	87.77%	95.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	86.67%	90.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.66%	94.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.43%	82.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.59%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.11%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.99%	89.62%
CHEMBL5747	Q92793	CREB-binding protein	84.88%	95.12%
CHEMBL261	P00915	Carbonic anhydrase I	84.72%	96.76%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.01%	96.86%
CHEMBL4208	P20618	Proteasome component C5	83.85%	90.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.59%	82.67%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.18%	100.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.07%	95.78%
CHEMBL2535	P11166	Glucose transporter	82.04%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.83%	89.50%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.82%	92.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.71%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.71%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.12%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.19%	93.99%

Plants that contains it

• Aconitum carmichaelii
• Antizoma angustifolia
• Artemisia argyi
• Catharanthus roseus
• Cissampelos capensis
• Cissampelos pareira
• Cyclea racemosa
• Euphorbia humifusa
• Lonicera japonica
• Morus alba
• Myrica rubra
• Orthosiphon aristatus var. aristatus
• Papaver somniferum
• Viscum articulatum
• Zea mays

Cross-Links

• PubChem: 10348927
• NPASS: NPC160842
• LOTUS: LTS0105068
• wikiData: Q27263227