3,4-Methylenedioxyphenanthrene-1-carboxylic acid

Details

• Internal ID: 0d1a656b-371e-4bae-ae7b-a8e0cbb70dc5
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: naphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
• InChI: InChI=1S/C16H10O4/c17-16(18)12-7-13-15(20-8-19-13)14-10-4-2-1-3-9(10)5-6-11(12)14/h1-7H,8H2,(H,17,18)
• InChI Key: QKUQFQPHGUCFMU-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₀O₄
• Molecular Weight: 266.25 g/mol
• Exact Mass: 266.05790880 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• RefChem:131737
• DEMETHYLARISTOFOLIN E
• CHEMBL512559
• Naphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9902	99.02%
Caco-2	+	0.6482	64.82%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7745	77.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9590	95.90%
OATP1B3 inhibitior	+	0.9070	90.70%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6533	65.33%
P-glycoprotein inhibitior	-	0.8491	84.91%
P-glycoprotein substrate	-	0.9588	95.88%
CYP3A4 substrate	-	0.6531	65.31%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8832	88.32%
CYP3A4 inhibition	+	0.5800	58.00%
CYP2C9 inhibition	-	0.5916	59.16%
CYP2C19 inhibition	-	0.7268	72.68%
CYP2D6 inhibition	-	0.7439	74.39%
CYP1A2 inhibition	+	0.9443	94.43%
CYP2C8 inhibition	-	0.7757	77.57%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8818	88.18%
Carcinogenicity (trinary)	Non-required	0.4537	45.37%
Eye corrosion	-	0.9733	97.33%
Eye irritation	+	0.9427	94.27%
Skin irritation	+	0.5859	58.59%
Skin corrosion	-	0.9340	93.40%
Ames mutagenesis	+	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8527	85.27%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.5382	53.82%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5099	50.99%
Acute Oral Toxicity (c)	III	0.7047	70.47%
Estrogen receptor binding	+	0.8396	83.96%
Androgen receptor binding	+	0.8332	83.32%
Thyroid receptor binding	+	0.5949	59.49%
Glucocorticoid receptor binding	+	0.8038	80.38%
Aromatase binding	+	0.7709	77.09%
PPAR gamma	+	0.8981	89.81%
Honey bee toxicity	-	0.9321	93.21%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9489	94.89%

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	98.11%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.53%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.11%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.25%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.14%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.90%	96.77%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	84.26%	87.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.67%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.12%	89.00%
CHEMBL2535	P11166	Glucose transporter	80.71%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.48%	94.45%

Plants that contains it

• Aristolochia manshuriensis

Cross-Links

• PubChem: 11780432
• NPASS: NPC44755
• LOTUS: LTS0276013
• wikiData: Q105223339