Methyl naphtho[2,1-g][1,3]benzodioxole-5-carboxylate

Details

• Internal ID: ec64ce2f-7baf-4216-b7a0-5d71e11a64e2
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: methyl naphtho[2,1-g][1,3]benzodioxole-5-carboxylate
• SMILES (Canonical): COC(=O)C1=CC2=C(C3=C1C=CC4=CC=CC=C43)OCO2
• SMILES (Isomeric): COC(=O)C1=CC2=C(C3=C1C=CC4=CC=CC=C43)OCO2
• InChI: InChI=1S/C17H12O4/c1-19-17(18)13-8-14-16(21-9-20-14)15-11-5-3-2-4-10(11)6-7-12(13)15/h2-8H,9H2,1H3
• InChI Key: GASGYTMJYGZAFG-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₄
• Molecular Weight: 280.27 g/mol
• Exact Mass: 280.07355886 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.9204	92.04%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7660	76.60%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.9421	94.21%
OATP1B3 inhibitior	+	0.9667	96.67%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8816	88.16%
P-glycoprotein inhibitior	-	0.6069	60.69%
P-glycoprotein substrate	-	0.8981	89.81%
CYP3A4 substrate	+	0.5241	52.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8317	83.17%
CYP3A4 inhibition	+	0.8954	89.54%
CYP2C9 inhibition	+	0.9139	91.39%
CYP2C19 inhibition	+	0.9315	93.15%
CYP2D6 inhibition	+	0.7218	72.18%
CYP1A2 inhibition	+	0.9361	93.61%
CYP2C8 inhibition	-	0.6078	60.78%
CYP inhibitory promiscuity	+	0.9344	93.44%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Warning	0.4991	49.91%
Eye corrosion	-	0.9479	94.79%
Eye irritation	+	0.7743	77.43%
Skin irritation	-	0.6402	64.02%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	+	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4942	49.42%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	+	0.5368	53.68%
skin sensitisation	+	0.5392	53.92%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6157	61.57%
Acute Oral Toxicity (c)	III	0.7597	75.97%
Estrogen receptor binding	+	0.9208	92.08%
Androgen receptor binding	+	0.8005	80.05%
Thyroid receptor binding	-	0.5115	51.15%
Glucocorticoid receptor binding	+	0.8958	89.58%
Aromatase binding	+	0.6149	61.49%
PPAR gamma	+	0.6641	66.41%
Honey bee toxicity	-	0.9043	90.43%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9409	94.09%

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	99.17%	91.11%
CHEMBL240	Q12809	HERG	98.63%	89.76%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.05%	92.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.52%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.63%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.49%	94.45%
CHEMBL2535	P11166	Glucose transporter	87.32%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.16%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.07%	96.77%
CHEMBL2581	P07339	Cathepsin D	86.42%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.06%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.85%	95.56%
CHEMBL4179	P45984	c-Jun N-terminal kinase 2	84.39%	90.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.29%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.12%	99.23%
CHEMBL5028	O14672	ADAM10	80.37%	97.50%

Plants that contains it

• Aristolochia kaempferi
• Aristolochia manshuriensis

Cross-Links

• PubChem: 85779428
• LOTUS: LTS0211571
• wikiData: Q105005605