Litebamine

Details

• Internal ID: 1aeb5b98-c945-48e1-9d36-f1eadac6ace6
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Phenanthrols
• IUPAC Name: 9,11-dimethoxy-2-methyl-3,4-dihydro-1H-naphtho[2,1-f]isoquinoline-8,12-diol
• SMILES (Canonical): CN1CCC2=C3C=CC4=CC(=C(C=C4C3=C(C(=C2C1)O)OC)OC)O
• SMILES (Isomeric): CN1CCC2=C3C=CC4=CC(=C(C=C4C3=C(C(=C2C1)O)OC)OC)O
• InChI: InChI=1S/C20H21NO4/c1-21-7-6-12-13-5-4-11-8-16(22)17(24-2)9-14(11)18(13)20(25-3)19(23)15(12)10-21/h4-5,8-9,22-23H,6-7,10H2,1-3H3
• InChI Key: QOWFEPGZJDCIKG-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.40 g/mol
• Exact Mass: 339.14705815 g/mol
• Topological Polar Surface Area (TPSA): 62.20 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 137031-56-2
• 9,11-dimethoxy-2-methyl-3,4-dihydro-1H-naphtho[2,1-f]isoquinoline-8,12-diol
• DTXSID30160040
• 9,11-dimethoxy-2-methyl-3,4-dihydro-1H-naphtho(2,1-f)isoquinoline-8,12-diol
• 9,13-dimethoxy-5-methyl-5-azatetracyclo(8.8.0.0^(2,7).0^(11,16))octadeca-1,7,9,11,13,15,17-heptaene-8,14-diol
• 9,13-dimethoxy-5-methyl-5-azatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-1,7,9,11,13,15,17-heptaene-8,14-diol
• RefChem:906627
• DTXCID4082531
• 1,2,3,4-Tetrahydro-9,11-dimethoxy-2-methylnaphth(2,1-f)isoquinoline-8,12-diol
• CHEMBL453173
• CHEBI:178482
• BDBM50250432
• 1,2,3,4-Tetrahydro-9,11-dimethoxy-2-methylnaphth[2,1-f]isoquinoline-8,12-diol, 9CI
• 9,11-dimethoxy-2-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]isoquinoline-8,12-diol
• 9,11-dimethoxy-2-methyl-3,4-dihydro-1H-naphtho[2,1-]isoquinoline-8,12-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8280	82.80%
Caco-2	+	0.8909	89.09%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6447	64.47%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9266	92.66%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.6033	60.33%
P-glycoprotein inhibitior	-	0.6843	68.43%
P-glycoprotein substrate	+	0.5178	51.78%
CYP3A4 substrate	+	0.5519	55.19%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8086	80.86%
CYP2C9 inhibition	-	0.8445	84.45%
CYP2C19 inhibition	-	0.7877	78.77%
CYP2D6 inhibition	+	0.6215	62.15%
CYP1A2 inhibition	+	0.7073	70.73%
CYP2C8 inhibition	+	0.5346	53.46%
CYP inhibitory promiscuity	-	0.9597	95.97%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6847	68.47%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8711	87.11%
Skin irritation	-	0.7383	73.83%
Skin corrosion	-	0.9336	93.36%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6647	66.47%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8872	88.72%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.9379	93.79%
Acute Oral Toxicity (c)	III	0.6436	64.36%
Estrogen receptor binding	+	0.7462	74.62%
Androgen receptor binding	+	0.5728	57.28%
Thyroid receptor binding	+	0.6394	63.94%
Glucocorticoid receptor binding	+	0.5808	58.08%
Aromatase binding	+	0.6976	69.76%
PPAR gamma	+	0.7143	71.43%
Honey bee toxicity	-	0.9423	94.23%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.8737	87.37%

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	98.69%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.04%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.42%	96.09%
CHEMBL2056	P21728	Dopamine D1 receptor	94.62%	91.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.51%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.31%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.06%	94.00%
CHEMBL4208	P20618	Proteasome component C5	92.79%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.41%	95.56%
CHEMBL2535	P11166	Glucose transporter	90.30%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.00%	89.62%
CHEMBL2581	P07339	Cathepsin D	89.13%	98.95%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	88.37%	93.65%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.80%	86.33%
CHEMBL5747	Q92793	CREB-binding protein	86.48%	95.12%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.55%	82.38%
CHEMBL217	P14416	Dopamine D2 receptor	84.50%	95.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.26%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.51%	95.89%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.76%	92.38%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.63%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.71%	89.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	81.30%	91.79%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.59%	100.00%

Plants that contains it

• Bursera simaruba
• Cephalaria leucantha
• Cissus quadrangularis
• Cleome trachysperma
• Delphinium denudatum
• Diplacus aurantiacus
• Ericameria laricifolia
• Litsea cubeba
• Loranthus longiflorus
• Melaleuca glauca
• Mentha longifolia subsp. longifolia
• Ormosia fordiana
• Orthosiphon wulfenioides
• Podocarpus elatus
• Polygala senega
• Solanum scabrum
• Stevia rebaudiana
• Vachellia karroo

Cross-Links

• PubChem: 196885
• NPASS: NPC60186
• ChEMBL: CHEMBL453173
• LOTUS: LTS0142332
• wikiData: Q83028419