Gusanlung A

Details

• Internal ID: aa822bd8-9bc5-4cd6-a315-02dd2f8bf78c
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (1S)-16-hydroxy-17-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-14-one
• SMILES (Canonical): COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2=O)OCO5)C=C1)O
• SMILES (Isomeric): COC1=C(C2=C(C[C@H]3C4=CC5=C(C=C4CCN3C2=O)OCO5)C=C1)O
• InChI: InChI=1S/C19H17NO5/c1-23-14-3-2-11-6-13-12-8-16-15(24-9-25-16)7-10(12)4-5-20(13)19(22)17(11)18(14)21/h2-3,7-8,13,21H,4-6,9H2,1H3/t13-/m0/s1
• InChI Key: XUOSVBINVLAZQP-ZDUSSCGKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₇NO₅
• Molecular Weight: 339.30 g/mol
• Exact Mass: 339.11067264 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.43
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 139220-06-7
• DTXSID40930397
• (1S)-16-hydroxy-17-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-14-one
• 8H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizin-8-one, 5,6,13,13a-tetrahydro-9-hydroxy-10-methoxy-, (S)-
• 9-Hydroxy-10-methoxy-5,6,13,13a-tetrahydro-2H,8H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-8-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8967	89.67%
Caco-2	+	0.8317	83.17%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7056	70.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8962	89.62%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8725	87.25%
P-glycoprotein inhibitior	-	0.7174	71.74%
P-glycoprotein substrate	-	0.7487	74.87%
CYP3A4 substrate	+	0.6268	62.68%
CYP2C9 substrate	-	0.5868	58.68%
CYP2D6 substrate	-	0.8202	82.02%
CYP3A4 inhibition	+	0.6793	67.93%
CYP2C9 inhibition	-	0.8626	86.26%
CYP2C19 inhibition	+	0.5152	51.52%
CYP2D6 inhibition	+	0.5441	54.41%
CYP1A2 inhibition	+	0.5562	55.62%
CYP2C8 inhibition	-	0.7316	73.16%
CYP inhibitory promiscuity	+	0.5643	56.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5573	55.73%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.8960	89.60%
Skin irritation	-	0.7882	78.82%
Skin corrosion	-	0.9476	94.76%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6568	65.68%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8710	87.10%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.4612	46.12%
Acute Oral Toxicity (c)	III	0.6356	63.56%
Estrogen receptor binding	+	0.8174	81.74%
Androgen receptor binding	+	0.5585	55.85%
Thyroid receptor binding	-	0.4937	49.37%
Glucocorticoid receptor binding	+	0.7888	78.88%
Aromatase binding	-	0.6507	65.07%
PPAR gamma	+	0.6551	65.51%
Honey bee toxicity	-	0.8847	88.47%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.7694	76.94%

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	98.37%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.10%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.49%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.13%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.98%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.10%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.16%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.00%	91.49%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.82%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.53%	93.40%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.35%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.23%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.02%	89.00%
CHEMBL1902	P62942	FK506-binding protein 1A	88.61%	97.05%
CHEMBL2056	P21728	Dopamine D1 receptor	88.49%	91.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.73%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.25%	92.62%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.82%	82.67%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	85.47%	96.86%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.11%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.64%	93.99%
CHEMBL217	P14416	Dopamine D2 receptor	84.60%	95.62%
CHEMBL4208	P20618	Proteasome component C5	83.84%	90.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.81%	82.38%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.19%	89.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.55%	100.00%
CHEMBL261	P00915	Carbonic anhydrase I	82.24%	96.76%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.21%	90.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.78%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.09%	95.78%

Plants that contains it

• Arcangelisia gusanlung

Cross-Links

• PubChem: 71450
• LOTUS: LTS0100014
• wikiData: Q82905741