2-[(13R)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]acetaldehyde

Details

• Internal ID: e8b6c8d2-8f6f-491e-b667-fd5f0c5b2712
• Taxonomy: Alkaloids and derivatives > Benzophenanthridine alkaloids > Dihydrobenzophenanthridine alkaloids
• IUPAC Name: 2-[(13R)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]acetaldehyde
• SMILES (Canonical): CN1C(C2=C(C=CC(=C2OC)OC)C3=C1C4=CC5=C(C=C4C=C3)OCO5)CC=O
• SMILES (Isomeric): CN1[C@@H](C2=C(C=CC(=C2OC)OC)C3=C1C4=CC5=C(C=C4C=C3)OCO5)CC=O
• InChI: InChI=1S/C23H21NO5/c1-24-17(8-9-25)21-14(6-7-18(26-2)23(21)27-3)15-5-4-13-10-19-20(29-12-28-19)11-16(13)22(15)24/h4-7,9-11,17H,8,12H2,1-3H3/t17-/m1/s1
• InChI Key: IINIJJSJDKBSBU-QGZVFWFLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₁NO₅
• Molecular Weight: 391.40 g/mol
• Exact Mass: 391.14197277 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.33
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9633	96.33%
Caco-2	+	0.8313	83.13%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.4000	40.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8959	89.59%
OATP1B3 inhibitior	+	0.9308	93.08%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9654	96.54%
P-glycoprotein inhibitior	+	0.9230	92.30%
P-glycoprotein substrate	+	0.6363	63.63%
CYP3A4 substrate	+	0.6116	61.16%
CYP2C9 substrate	-	0.6027	60.27%
CYP2D6 substrate	+	0.4492	44.92%
CYP3A4 inhibition	+	0.8656	86.56%
CYP2C9 inhibition	-	0.5984	59.84%
CYP2C19 inhibition	+	0.8802	88.02%
CYP2D6 inhibition	-	0.5430	54.30%
CYP1A2 inhibition	+	0.5878	58.78%
CYP2C8 inhibition	+	0.5125	51.25%
CYP inhibitory promiscuity	+	0.7930	79.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4864	48.64%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9674	96.74%
Skin irritation	-	0.8167	81.67%
Skin corrosion	-	0.9566	95.66%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7384	73.84%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.5284	52.84%
skin sensitisation	-	0.8699	86.99%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7776	77.76%
Acute Oral Toxicity (c)	III	0.7688	76.88%
Estrogen receptor binding	+	0.8811	88.11%
Androgen receptor binding	+	0.7994	79.94%
Thyroid receptor binding	+	0.6503	65.03%
Glucocorticoid receptor binding	+	0.9089	90.89%
Aromatase binding	-	0.5754	57.54%
PPAR gamma	+	0.7234	72.34%
Honey bee toxicity	-	0.8213	82.13%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8639	86.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.16%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.27%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	95.25%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.68%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.40%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.09%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.47%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.89%	98.95%
CHEMBL4208	P20618	Proteasome component C5	91.31%	90.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	90.72%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	90.05%	90.24%
CHEMBL5747	Q92793	CREB-binding protein	87.78%	95.12%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.72%	94.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.61%	80.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.02%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.86%	99.17%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	83.64%	92.38%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.28%	89.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.88%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	81.78%	94.75%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.28%	89.44%
CHEMBL2535	P11166	Glucose transporter	80.67%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.44%	100.00%

Plants that contains it

• Zanthoxylum tsihanimposa

Cross-Links

• PubChem: 163059312
• LOTUS: LTS0270365
• wikiData: Q105113634