Thaliporphine

Details

• Internal ID: e50fde86-a4d6-451f-8657-13df4095819d
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (6aS)-2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-1-ol
• SMILES (Canonical): CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC)O)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)OC)O)OC
• InChI: InChI=1S/C20H23NO4/c1-21-6-5-11-8-17(25-4)20(22)19-13-10-16(24-3)15(23-2)9-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3/t14-/m0/s1
• InChI Key: SAERKXUSZPTMCQ-AWEZNQCLSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.40 g/mol
• Exact Mass: 341.16270821 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• (+)-Thaliporphine
• 5083-88-5
• (6As)-2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-1-ol
• Oc1c(OC)cc2CCN(C)C3Cc4cc(OC)c(OC)cc4c1c23
• CHEMBL1397308
• SCHEMBL14029527
• DTXSID601345982
• NCGC00017380-02
• NCGC00142558-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9379	93.79%
Caco-2	+	0.8732	87.32%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5800	58.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8931	89.31%
OATP1B3 inhibitior	+	0.9525	95.25%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.6427	64.27%
P-glycoprotein inhibitior	-	0.7162	71.62%
P-glycoprotein substrate	-	0.6423	64.23%
CYP3A4 substrate	+	0.5995	59.95%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.7998	79.98%
CYP2C9 inhibition	-	0.9152	91.52%
CYP2C19 inhibition	-	0.8495	84.95%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.8522	85.22%
CYP2C8 inhibition	-	0.8047	80.47%
CYP inhibitory promiscuity	-	0.9463	94.63%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7057	70.57%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9690	96.90%
Skin irritation	-	0.7512	75.12%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3955	39.55%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.8199	81.99%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8974	89.74%
Acute Oral Toxicity (c)	III	0.8040	80.40%
Estrogen receptor binding	+	0.7147	71.47%
Androgen receptor binding	-	0.5984	59.84%
Thyroid receptor binding	+	0.7127	71.27%
Glucocorticoid receptor binding	+	0.8168	81.68%
Aromatase binding	+	0.5952	59.52%
PPAR gamma	+	0.7389	73.89%
Honey bee toxicity	-	0.9093	90.93%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.8720	87.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	5011.9 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	39810.7 nM	Potency	via CMAUP
CHEMBL4801	P29466	Caspase-1	25118.9 nM	Potency	via CMAUP
CHEMBL3468	P55210	Caspase-7	31622.8 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	34435.5 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	31622.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	44668.4 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.00%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	96.71%	95.62%
CHEMBL2056	P21728	Dopamine D1 receptor	95.05%	91.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.77%	91.79%
CHEMBL2581	P07339	Cathepsin D	93.61%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.18%	92.94%
CHEMBL1951	P21397	Monoamine oxidase A	91.56%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.88%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.64%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.25%	95.89%
CHEMBL4208	P20618	Proteasome component C5	88.99%	90.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.66%	91.03%
CHEMBL3438	Q05513	Protein kinase C zeta	87.65%	88.48%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.15%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.04%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.83%	86.33%
CHEMBL5747	Q92793	CREB-binding protein	85.64%	95.12%
CHEMBL2535	P11166	Glucose transporter	83.31%	98.75%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	82.70%	95.34%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	82.32%	96.86%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.14%	89.62%
CHEMBL3474	P14555	Phospholipase A2 group IIA	81.72%	94.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.48%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.39%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.04%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.32%	89.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.00%	92.38%

Plants that contains it

• Annona purpurea
• Berberis cretica
• Berberis integerrima
• Berberis oblonga
• Berberis thunbergii
• Coleostephus myconis
• Corydalis gortschakovii
• Corydalis yanhusuo
• Croton lechleri
• Glaucium fimbrilligerum
• Glaucium flavum
• Glaucium grandiflorum
• Ligularia nelumbifolia
• Liriodendron tulipifera
• Plectranthus ernstii
• Thalictrum alpinum
• Thalictrum foetidum
• Thalictrum isopyroides
• Thalictrum minus
• Thalictrum simplex

Cross-Links

• PubChem: 6992288
• NPASS: NPC78222
• ChEMBL: CHEMBL1397308
• LOTUS: LTS0131877
• wikiData: Q105248814