3-Hydroxy-4-methoxy-10-nitrophenanthrene-1-carboxylic acid

Details

• Internal ID: 3a4f4087-1ad5-42d4-9837-bddcef6bb405
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Aristolochic acids and derivatives
• IUPAC Name: 3-hydroxy-4-methoxy-10-nitrophenanthrene-1-carboxylic acid
• SMILES (Canonical): COC1=C(C=C(C2=C1C3=CC=CC=C3C=C2[N+](=O)[O-])C(=O)O)O
• SMILES (Isomeric): COC1=C(C=C(C2=C1C3=CC=CC=C3C=C2[N+](=O)[O-])C(=O)O)O
• InChI: InChI=1S/C16H11NO6/c1-23-15-12(18)7-10(16(19)20)13-11(17(21)22)6-8-4-2-3-5-9(8)14(13)15/h2-7,18H,1H3,(H,19,20)
• InChI Key: WOPNYAPWPGRNTF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₁NO₆
• Molecular Weight: 313.26 g/mol
• Exact Mass: 313.05863707 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9197	91.97%
Caco-2	-	0.6307	63.07%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5594	55.94%
OATP2B1 inhibitior	-	0.7175	71.75%
OATP1B1 inhibitior	+	0.8925	89.25%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6140	61.40%
P-glycoprotein inhibitior	-	0.8473	84.73%
P-glycoprotein substrate	-	0.9419	94.19%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7861	78.61%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.8818	88.18%
CYP2C9 inhibition	-	0.6062	60.62%
CYP2C19 inhibition	-	0.8050	80.50%
CYP2D6 inhibition	-	0.9436	94.36%
CYP1A2 inhibition	-	0.7412	74.12%
CYP2C8 inhibition	+	0.6243	62.43%
CYP inhibitory promiscuity	-	0.7126	71.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.5458	54.58%
Carcinogenicity (trinary)	Warning	0.4269	42.69%
Eye corrosion	-	0.9791	97.91%
Eye irritation	+	0.5985	59.85%
Skin irritation	-	0.7396	73.96%
Skin corrosion	-	0.9633	96.33%
Ames mutagenesis	+	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8907	89.07%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.9136	91.36%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.6800	68.00%
Nephrotoxicity	-	0.5783	57.83%
Acute Oral Toxicity (c)	III	0.6784	67.84%
Estrogen receptor binding	+	0.8281	82.81%
Androgen receptor binding	+	0.5715	57.15%
Thyroid receptor binding	-	0.5151	51.51%
Glucocorticoid receptor binding	+	0.9138	91.38%
Aromatase binding	+	0.6254	62.54%
PPAR gamma	+	0.7480	74.80%
Honey bee toxicity	-	0.9459	94.59%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9889	98.89%

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	95.05%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.94%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.92%	86.33%
CHEMBL2535	P11166	Glucose transporter	91.73%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.36%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.79%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.41%	99.23%
CHEMBL1255126	O15151	Protein Mdm4	87.90%	90.20%
CHEMBL3902	P09211	Glutathione S-transferase Pi	86.89%	93.81%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.33%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.76%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.60%	94.62%

Plants that contains it

• Aristolochia liukiuensis
• Aristolochia zollingeriana

Cross-Links

• PubChem: 163192830
• LOTUS: LTS0096553
• wikiData: Q105309632