Maculine

Details

• Internal ID: c3689ceb-909a-40c8-b1d9-31e6dddc67fc
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Furanoquinolines
• IUPAC Name: 8-methoxy-4,12,14-trioxa-2-azatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),2,5,7,9,11(15)-hexaene
• SMILES (Canonical): COC1=C2C=COC2=NC3=CC4=C(C=C31)OCO4
• SMILES (Isomeric): COC1=C2C=COC2=NC3=CC4=C(C=C31)OCO4
• InChI: InChI=1S/C13H9NO4/c1-15-12-7-2-3-16-13(7)14-9-5-11-10(4-8(9)12)17-6-18-11/h2-5H,6H2,1H3
• InChI Key: VPNYHHBCMOYPCJ-UHFFFAOYSA-N
• Popularity: 42 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₉NO₄
• Molecular Weight: 243.21 g/mol
• Exact Mass: 243.05315777 g/mol
• Topological Polar Surface Area (TPSA): 53.70 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.72
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• Maculin
• 524-89-0
• Makulin
• CCRIS 3577
• 1,3-Dioxolo(4,5-g)furo(2,3-b)quinoline, 9-methoxy-
• BRN 0255599
• 67W5VPJ6AX
• CHEBI:6629
• 9-Methoxy-1,3-dioxolo(4,5-g)furo(2,3-b)quinoline
• NSC-94658
• 9-Methoxy-[1,3]dioxolo[4,5-g]furo[2,3-b]quinoline
• 4-27-00-06795 (Beilstein Handbook Reference)
• 1,3-Dioxolo[4,5-g]furo[2,3-b]quinoline, 9-methoxy-
• 8-methoxy-4,12,14-trioxa-2-azatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),2,5,7,9,11(15)-hexaene
• 9-Methoxy-1,3-dioxolo[4,5-g]furo[2,3-b]quinoline
• 9-Methoxy[1,3]dioxolo[4,5-g]furo[2,3-b]quinoline
• UNII-67W5VPJ6AX
• CHEMBL503675
• DTXSID90200416
• VPNYHHBCMOYPCJ-UHFFFAOYSA-N
• NSC94658
• NSC 94658
• LS-62689
• XM161788
• 1,5-g]furo[2,3-b]quinoline, 9-methoxy-
• Q27107282
• 9-Methoxy[1,3]dioxolo[4,5-g]furo[2,3-b]quinoline #
• 9-Methoxy-2H-1,3-dioxolano[4,5-g]furano[2,3-b]quinoline

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	+	0.6450	64.50%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6158	61.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9677	96.77%
OATP1B3 inhibitior	+	0.9637	96.37%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.4841	48.41%
P-glycoprotein inhibitior	-	0.8957	89.57%
P-glycoprotein substrate	-	0.9041	90.41%
CYP3A4 substrate	-	0.5760	57.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7250	72.50%
CYP3A4 inhibition	+	0.7452	74.52%
CYP2C9 inhibition	-	0.5693	56.93%
CYP2C19 inhibition	+	0.6164	61.64%
CYP2D6 inhibition	-	0.5264	52.64%
CYP1A2 inhibition	+	0.9407	94.07%
CYP2C8 inhibition	-	0.6451	64.51%
CYP inhibitory promiscuity	+	0.8248	82.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4504	45.04%
Eye corrosion	-	0.9845	98.45%
Eye irritation	+	0.6499	64.99%
Skin irritation	-	0.8042	80.42%
Skin corrosion	-	0.9601	96.01%
Ames mutagenesis	+	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7295	72.95%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.7600	76.00%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.5962	59.62%
Acute Oral Toxicity (c)	III	0.7162	71.62%
Estrogen receptor binding	+	0.7606	76.06%
Androgen receptor binding	+	0.6352	63.52%
Thyroid receptor binding	+	0.6477	64.77%
Glucocorticoid receptor binding	+	0.8724	87.24%
Aromatase binding	+	0.8674	86.74%
PPAR gamma	+	0.6463	64.63%
Honey bee toxicity	-	0.8842	88.42%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	-	0.6211	62.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.41%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.55%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.53%	94.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	91.49%	80.96%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.36%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.18%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.95%	96.00%
CHEMBL240	Q12809	HERG	89.36%	89.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.79%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.59%	94.80%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	87.63%	94.03%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	86.42%	85.49%
CHEMBL5747	Q92793	CREB-binding protein	86.02%	95.12%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.51%	82.67%
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	84.55%	95.39%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.20%	86.33%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	84.09%	89.44%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.12%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	82.98%	94.73%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.66%	85.30%

Plants that contains it

• Aconitum volubile
• Aeollanthus buchnerianus
• Cynoglossum viridiflorum
• Derris montana
• Echium plantagineum
• Esenbeckia berlandieri subsp. litoralis
• Esenbeckia grandiflora
• Esenbeckia leiocarpa
• Esenbeckia pilocarpoides
• Flindersia maculosa
• Flindersia xanthoxyla
• Helianthus niveus
• Hernandia sonora
• Leptospermum recurvum
• Ptelea aptera
• Vepris afzelii
• Vepris nobilis
• Vepris soyauxii
• Vepris suaveolens
• Vepris unifoliolata

Cross-Links

• PubChem: 68232
• NPASS: NPC168922
• ChEMBL: CHEMBL503675
• LOTUS: LTS0036915
• wikiData: Q27107282