Aporeine

Details

• Internal ID: f2a419e5-bc71-45e0-9447-cc17ddbdaec4
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (12S)-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene
• SMILES (Canonical): CN1CCC2=CC3=C(C4=C2C1CC5=CC=CC=C54)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=CC=CC=C54)OCO3
• InChI: InChI=1S/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3/t14-/m0/s1
• InChI Key: JCTYWRARKVGOBK-AWEZNQCLSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₇NO₂
• Molecular Weight: 279.30 g/mol
• Exact Mass: 279.125928785 g/mol
• Topological Polar Surface Area (TPSA): 21.70 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Aporrheine
• (+)-Roemerine
• D-Isoremerine
• Apo-rheine
• D-Remerine
• Aporeine [MI]
• (+)-Aporheine
• S-(+)-Roemerine
• 1,2-Methylenedioxyaporphine
• Aporheine
• 2030-53-7
• UNII-9C0X3XW6QA
• 9C0X3XW6QA
• (7aS)-6,7,7a,8-Tetrahydro-7-methyl-5H-benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline
• (12S)-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene
• (7aS)-6,7,7a,8-Tetrahydro-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline
• SCHEMBL678048
• CHEMBL2365576
• 7-Methyl-6,7,7a,8-tetrahydro-5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinoline #
• JCTYWRARKVGOBK-AWEZNQCLSA-N
• 6a.alpha.-Aporphine, 1,2-(methylenedioxy)-
• Q27272338
• 5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline, 6,7,7a,8-tetrahydro-7-methyl-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9873	98.73%
Caco-2	+	0.9409	94.09%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Lysosomes	0.3779	37.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9351	93.51%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7018	70.18%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.7372	73.72%
CYP3A4 substrate	+	0.5830	58.30%
CYP2C9 substrate	-	0.5820	58.20%
CYP2D6 substrate	+	0.6456	64.56%
CYP3A4 inhibition	-	0.6587	65.87%
CYP2C9 inhibition	-	0.9303	93.03%
CYP2C19 inhibition	-	0.7085	70.85%
CYP2D6 inhibition	+	0.8736	87.36%
CYP1A2 inhibition	+	0.6510	65.10%
CYP2C8 inhibition	-	0.8939	89.39%
CYP inhibitory promiscuity	-	0.6167	61.67%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6035	60.35%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9914	99.14%
Skin irritation	-	0.6945	69.45%
Skin corrosion	-	0.8763	87.63%
Ames mutagenesis	+	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7546	75.46%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8494	84.94%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7105	71.05%
Acute Oral Toxicity (c)	III	0.5875	58.75%
Estrogen receptor binding	+	0.5911	59.11%
Androgen receptor binding	+	0.6771	67.71%
Thyroid receptor binding	-	0.5734	57.34%
Glucocorticoid receptor binding	+	0.6106	61.06%
Aromatase binding	-	0.7105	71.05%
PPAR gamma	+	0.5714	57.14%
Honey bee toxicity	-	0.8725	87.25%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.7800	78.00%
Fish aquatic toxicity	+	0.8279	82.79%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL229	P35348	Alpha-1a adrenergic receptor	251.19 nM	Ki	via Super-PRED
CHEMBL223	P25100	Alpha-1d adrenergic receptor	630.96 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.19%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.75%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.34%	93.40%
CHEMBL1951	P21397	Monoamine oxidase A	94.24%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.03%	95.56%
CHEMBL2056	P21728	Dopamine D1 receptor	91.89%	91.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.97%	91.11%
CHEMBL217	P14416	Dopamine D2 receptor	89.06%	95.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.46%	86.33%
CHEMBL240	Q12809	HERG	85.79%	89.76%
CHEMBL5805	Q9NR97	Toll-like receptor 8	85.77%	96.25%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	83.90%	83.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.58%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	82.81%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.76%	100.00%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	81.45%	81.29%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.28%	82.67%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.65%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.54%	95.89%

Plants that contains it

• Magnolia obovata
• Magnolia officinalis
• Nelumbo nucifera
• Papaver cambricum
• Papaver dubium
• Papaver pilosum
• Papaver rhoeas

Cross-Links

• PubChem: 800239
• NPASS: NPC201636
• LOTUS: LTS0250679
• wikiData: Q27272338