Glaziovine

Details

• Internal ID: fd8cab47-c6af-4552-9781-961f246c6604
• Taxonomy: Alkaloids and derivatives > Proaporphines
• IUPAC Name: 11-hydroxy-10-methoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
• SMILES (Canonical): CN1CCC2=CC(=C(C3=C2C1CC34C=CC(=O)C=C4)O)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C3=C2C1CC34C=CC(=O)C=C4)O)OC
• InChI: InChI=1S/C18H19NO3/c1-19-8-5-11-9-14(22-2)17(21)16-15(11)13(19)10-18(16)6-3-12(20)4-7-18/h3-4,6-7,9,13,21H,5,8,10H2,1-2H3
• InChI Key: PNJUPRNTSWJWAX-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.30 g/mol
• Exact Mass: 297.13649347 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.27
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 17127-48-9
• Glaziovine [INN]
• (+/-)-Glaziovine
• 6'-Hydroxy-5'-methoxy-1'-methyl-2',3',8',8a'-tetrahydro-1'H-spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[ij]isoquinolin]-4-one
• NSC-146052
• Suavedol
• KE7J8A65P6
• Glaziovine, L-
• N-Methylcrotsparine
• NSC141545
• Glaziovinum
• Crotsparine, 6-methyl-
• P.M. 297
• (+/-)-2',3',8',8a'-Tetrahydro-6'-hydroxy-5'-methoxy-1'-methylspiro[2,5-cyclohexadiene-1,7'(1'H)-cyclopent[ij]isoquinolin]-4-one
• (+-)-Glaziovine
• Glaziovinum [INN-Latin]
• Glaziovina [INN-Spanish]
• glaziovinae
• UNII-KE7J8A65P6
• NSC 146052
• C09457
• (.+-.)-Glaziovine
• AI3-34588
• AC1L9CHE
• Glaziovine, (.+-.)-
• SCHEMBL554440
• CHEMBL1980854
• DTXSID90864739
• NSC146052
• AKOS022181549
• NSC-141545
• NCI60_000910
• 2,3,4,6-TETRA-O-BENZOYL-ALPHA-D-GLUCOPYRANOSYLBROMIDE
• 11-hydroxy-10-methoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
• Spiro(2,5-cyclohexadiene-1,7'(1'H)-cyclopent(ij)isoquinolin)-4-one, 2',3',8',8'a-tetrahydro-6'-hydroxy-5'-methoxy-1'-methyl-, (+-)-
• Spiro[2,7'(1'H)-cyclopent[ij]isoquinolin]-4-one, 2',3',8',8'a-tetrahydro-6'-hydroxy-5'-methoxy-1'-methyl-, (.+-.)-
• Spiro[2,7'(1'H)-cyclopent[ij]isoquinolin]-4-one, 2',3',8',8'a-tetrahydro-6'-hydroxy-5'-methoxy-1'-methyl-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9816	98.16%
Caco-2	+	0.6976	69.76%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7124	71.24%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.9366	93.66%
OATP1B3 inhibitior	+	0.9537	95.37%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	-	0.5194	51.94%
P-glycoprotein inhibitior	-	0.8725	87.25%
P-glycoprotein substrate	+	0.5249	52.49%
CYP3A4 substrate	+	0.6898	68.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4065	40.65%
CYP3A4 inhibition	-	0.8112	81.12%
CYP2C9 inhibition	-	0.8121	81.21%
CYP2C19 inhibition	-	0.8446	84.46%
CYP2D6 inhibition	+	0.7022	70.22%
CYP1A2 inhibition	-	0.5408	54.08%
CYP2C8 inhibition	-	0.8621	86.21%
CYP inhibitory promiscuity	-	0.7755	77.55%
UGT catelyzed	+	0.7362	73.62%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6768	67.68%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9842	98.42%
Skin irritation	-	0.7413	74.13%
Skin corrosion	-	0.9352	93.52%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4406	44.06%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.7529	75.29%
skin sensitisation	-	0.8577	85.77%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.9143	91.43%
Acute Oral Toxicity (c)	III	0.8030	80.30%
Estrogen receptor binding	+	0.5398	53.98%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5776	57.76%
Glucocorticoid receptor binding	-	0.6049	60.49%
Aromatase binding	+	0.5239	52.39%
PPAR gamma	+	0.5343	53.43%
Honey bee toxicity	-	0.8733	87.33%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9381	93.81%

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	98.96%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.26%	95.56%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	95.04%	91.03%
CHEMBL2056	P21728	Dopamine D1 receptor	94.49%	91.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.40%	93.40%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.45%	91.11%
CHEMBL217	P14416	Dopamine D2 receptor	92.09%	95.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.61%	95.89%
CHEMBL2581	P07339	Cathepsin D	89.13%	98.95%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	88.04%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.66%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.24%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.99%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.91%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.63%	93.99%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.56%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.21%	96.77%
CHEMBL4208	P20618	Proteasome component C5	84.16%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.46%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.28%	89.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.09%	82.38%
CHEMBL2535	P11166	Glucose transporter	80.99%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.94%	100.00%

Plants that contains it

• Annona purpurea
• Cissampelos capensis
• Croton bonplandianus
• Hypserpa nitida
• Litsea cubeba
• Neolitsea konishii
• Ocotea lancifolia
• Xylopia parviflora

Cross-Links

• PubChem: 65631
• LOTUS: LTS0040406
• wikiData: Q81986394