Oxopurpureine

Details

• Internal ID: dafac6c4-fa93-4568-b9ed-66a40623ad01
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: 4,5,14,15,16-pentamethoxy-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C3=C(C(=C(C4=C3C(=NC=C4)C2=O)OC)OC)OC)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C3=C(C(=C(C4=C3C(=NC=C4)C2=O)OC)OC)OC)OC
• InChI: InChI=1S/C21H19NO6/c1-24-13-8-11-12(9-14(13)25-2)18(23)17-15-10(6-7-22-17)19(26-3)21(28-5)20(27-4)16(11)15/h6-9H,1-5H3
• InChI Key: AZTLZBDEFBJZQG-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₉NO₆
• Molecular Weight: 381.40 g/mol
• Exact Mass: 381.12123733 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.49
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 32845-27-5
• MLS000574936
• NSC 141544
• SMR000156318
• 4,5,14,15,16-pentamethoxy-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one
• HMS2220I24
• CHEMBL456295
• cid_284998
• BDBM52490
• DTXSID00301165
• CHEBI:188967
• NSC141544
• 1,2,3,9,10-Pentamethoxyoxoaporphine
• NSC-141544
• 1,2,3,9,10-Pentamethoxy-7H-dibenzo[de,g]quinolin-7-one, 9CI
• 4,5,14,15,16-pentamethoxy-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(16),2,4,6,9(17),10,12,14-octaen-8-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.8349	83.49%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5338	53.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9523	95.23%
OATP1B3 inhibitior	+	0.9817	98.17%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.5985	59.85%
P-glycoprotein inhibitior	-	0.4392	43.92%
P-glycoprotein substrate	-	0.7811	78.11%
CYP3A4 substrate	+	0.5685	56.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7304	73.04%
CYP3A4 inhibition	+	0.7138	71.38%
CYP2C9 inhibition	-	0.9701	97.01%
CYP2C19 inhibition	-	0.5222	52.22%
CYP2D6 inhibition	-	0.8747	87.47%
CYP1A2 inhibition	+	0.9331	93.31%
CYP2C8 inhibition	+	0.6089	60.89%
CYP inhibitory promiscuity	+	0.7213	72.13%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6378	63.78%
Eye corrosion	-	0.9900	99.00%
Eye irritation	+	0.5717	57.17%
Skin irritation	-	0.8346	83.46%
Skin corrosion	-	0.9809	98.09%
Ames mutagenesis	+	0.7536	75.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.5355	53.55%
Micronuclear	+	0.7059	70.59%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.9503	95.03%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6911	69.11%
Acute Oral Toxicity (c)	II	0.5437	54.37%
Estrogen receptor binding	+	0.8795	87.95%
Androgen receptor binding	-	0.5119	51.19%
Thyroid receptor binding	+	0.8434	84.34%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.7398	73.98%
PPAR gamma	+	0.7305	73.05%
Honey bee toxicity	-	0.8678	86.78%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	-	0.5201	52.01%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	12589.3 nM	Potency	via CMAUP
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	11220.2 nM	Potency	via CMAUP
CHEMBL5514	P42858	Huntingtin	11220.2 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	19952.6 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	10000 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	11220.2 nM	Potency	via CMAUP
CHEMBL1741200	Q2TB90	Putative hexokinase HKDC1	12100 nM; 10100 nM	IC50; IC50	via CMAUP; via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	31622.8 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.88%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.83%	94.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	92.74%	96.67%
CHEMBL2535	P11166	Glucose transporter	91.95%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.31%	86.33%
CHEMBL5014	O43353	Serine/threonine-protein kinase RIPK2	90.93%	86.79%
CHEMBL5747	Q92793	CREB-binding protein	89.84%	95.12%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	89.70%	94.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.33%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.48%	96.00%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	88.44%	96.47%
CHEMBL2581	P07339	Cathepsin D	88.07%	98.95%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	85.02%	96.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.99%	92.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.39%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.23%	85.14%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.79%	100.00%
CHEMBL4302	P08183	P-glycoprotein 1	83.16%	92.98%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.14%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.40%	99.23%

Plants that contains it

• Annona mucosa
• Annona purpurea
• Annona squamosa
• Thalictrum microgynum

Cross-Links

• PubChem: 284998
• NPASS: NPC90875
• ChEMBL: CHEMBL456295
• LOTUS: LTS0179104
• wikiData: Q82044802