Norisoboldine

Details

• Internal ID: 864b53db-9e50-4dde-86db-e2ec7b393189
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (6aS)-2,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,9-diol
• SMILES (Canonical): COC1=C(C2=C3C(CC4=CC(=C(C=C42)OC)O)NCCC3=C1)O
• SMILES (Isomeric): COC1=C(C2=C3[C@H](CC4=CC(=C(C=C42)OC)O)NCCC3=C1)O
• InChI: InChI=1S/C18H19NO4/c1-22-14-8-11-10(6-13(14)20)5-12-16-9(3-4-19-12)7-15(23-2)18(21)17(11)16/h6-8,12,19-21H,3-5H2,1-2H3/t12-/m0/s1
• InChI Key: HORZNQYQXBFWNZ-LBPRGKRZSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.30 g/mol
• Exact Mass: 313.13140809 g/mol
• Topological Polar Surface Area (TPSA): 71.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 23599-69-1
• (+)-Laurelliptine
• (6aS)-2,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,9-diol
• (+)-Norisoboldine
• D05GLT
• CHEMBL375902
• DTXSID801316226
• BCP18952
• HY-N0586
• MFCD09953815
• s9092
• AKOS030530135
• CCG-267616
• CS-6003
• AC-34581
• BS-42172
• Q-100304
• 4H-Dibenzo[de,g]quinoline-1,9-diol, 5,6,6a,7-tetrahydro-2,10-dimethoxy-, (6aS)-
• 4H-Dibenzo[de,g]quinoline-1,9-diol, 5,6,6a,7-tetrahydro-2,10-dimethoxy-, (S)-
• 5,6,6aalpha,7-Tetrahydro-2,10-dimethoxy-4H-dibenzo[de,g]quinoline-1,9-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9664	96.64%
Caco-2	+	0.6176	61.76%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6245	62.45%
OATP2B1 inhibitior	-	0.8493	84.93%
OATP1B1 inhibitior	+	0.8891	88.91%
OATP1B3 inhibitior	+	0.9574	95.74%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.4640	46.40%
P-glycoprotein inhibitior	-	0.8654	86.54%
P-glycoprotein substrate	-	0.6021	60.21%
CYP3A4 substrate	+	0.5703	57.03%
CYP2C9 substrate	-	0.6360	63.60%
CYP2D6 substrate	+	0.7728	77.28%
CYP3A4 inhibition	-	0.8529	85.29%
CYP2C9 inhibition	-	0.9327	93.27%
CYP2C19 inhibition	-	0.8031	80.31%
CYP2D6 inhibition	+	0.5852	58.52%
CYP1A2 inhibition	-	0.5238	52.38%
CYP2C8 inhibition	+	0.5860	58.60%
CYP inhibitory promiscuity	-	0.8538	85.38%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7423	74.23%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9046	90.46%
Skin irritation	-	0.6813	68.13%
Skin corrosion	-	0.9192	91.92%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8787	87.87%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8497	84.97%
Acute Oral Toxicity (c)	III	0.5164	51.64%
Estrogen receptor binding	+	0.7281	72.81%
Androgen receptor binding	-	0.5376	53.76%
Thyroid receptor binding	+	0.7990	79.90%
Glucocorticoid receptor binding	+	0.7738	77.38%
Aromatase binding	-	0.5315	53.15%
PPAR gamma	+	0.7920	79.20%
Honey bee toxicity	-	0.8681	86.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	-	0.5662	56.62%

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	98.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.02%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.67%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.86%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.86%	97.09%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	92.31%	91.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.85%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	90.80%	88.48%
CHEMBL4208	P20618	Proteasome component C5	90.30%	90.00%
CHEMBL2581	P07339	Cathepsin D	89.75%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.59%	86.33%
CHEMBL217	P14416	Dopamine D2 receptor	89.56%	95.62%
CHEMBL213	P08588	Beta-1 adrenergic receptor	88.10%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.70%	93.99%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.60%	96.21%
CHEMBL2056	P21728	Dopamine D1 receptor	86.07%	91.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	85.84%	98.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.37%	99.17%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.82%	93.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.57%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.89%	92.62%
CHEMBL2535	P11166	Glucose transporter	83.84%	98.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.46%	91.03%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	82.32%	95.55%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	82.27%	92.68%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.62%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.15%	95.56%
CHEMBL3194	P02766	Transthyretin	80.07%	90.71%

Plants that contains it

• Annona squamosa
• Beilschmiedia elliptica
• Cassytha pubescens
• Cocculus laurifolius
• Corydalis cava
• Corydalis stricta
• Croton lechleri
• Cryptocarya chinensis
• Fissistigma oldhamii
• Illigera pentaphylla
• Lindera aggregata
• Monanthotaxis cauliflora
• Ocotea caesia
• Pachygone ovata
• Platycladus orientalis
• Stephania cephalantha

Cross-Links

• PubChem: 14539911
• NPASS: NPC249033
• LOTUS: LTS0266234
• wikiData: Q105031498