Rhinacanthone

Details

• Internal ID: d40d8a76-9ef3-4980-a12d-d417b04d4635
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: 3,3-dimethyl-2,4-dihydrobenzo[h]chromene-5,6-dione
• InChI: InChI=1S/C15H14O3/c1-15(2)7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-8-15/h3-6H,7-8H2,1-2H3
• InChI Key: GAQRLJKQPBBUSK-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27 g/mol
• Exact Mass: 242.094294304 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.61
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 171522-36-4
• 3,3-dimethyl-2,4-dihydrobenzo[h]chromene-5,6-dione
• DTXSID60169127
• 3,4-dihydro-3,3-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione
• 3,3-dimethyl-2,4-dihydrobenzo(h)chromene-5,6-dione
• RefChem:179163
• DTXCID3091618
• CHEMBL512946

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9965	99.65%
Caco-2	+	0.8268	82.68%
Blood Brain Barrier	+	0.5428	54.28%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8481	84.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9498	94.98%
OATP1B3 inhibitior	+	0.9757	97.57%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7048	70.48%
P-glycoprotein inhibitior	-	0.9116	91.16%
P-glycoprotein substrate	-	0.9360	93.60%
CYP3A4 substrate	-	0.5173	51.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7930	79.30%
CYP3A4 inhibition	-	0.7387	73.87%
CYP2C9 inhibition	+	0.8534	85.34%
CYP2C19 inhibition	+	0.8682	86.82%
CYP2D6 inhibition	-	0.5392	53.92%
CYP1A2 inhibition	+	0.7804	78.04%
CYP2C8 inhibition	-	0.9549	95.49%
CYP inhibitory promiscuity	+	0.7295	72.95%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9418	94.18%
Carcinogenicity (trinary)	Non-required	0.6296	62.96%
Eye corrosion	-	0.9789	97.89%
Eye irritation	+	0.8072	80.72%
Skin irritation	-	0.7216	72.16%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6049	60.49%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.5794	57.94%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.8707	87.07%
Acute Oral Toxicity (c)	III	0.5858	58.58%
Estrogen receptor binding	+	0.8342	83.42%
Androgen receptor binding	+	0.7374	73.74%
Thyroid receptor binding	-	0.5612	56.12%
Glucocorticoid receptor binding	-	0.6634	66.34%
Aromatase binding	+	0.5632	56.32%
PPAR gamma	+	0.7061	70.61%
Honey bee toxicity	-	0.8498	84.98%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9895	98.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.52%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.11%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.54%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.27%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	88.13%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.03%	99.23%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.59%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.52%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.55%	96.77%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.51%	96.38%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.05%	97.14%

Plants that contains it

• Aeonium cuneatum
• Lithospermum canescens
• Rhinacanthus nasutus
• Rhinacanthus nasutus

Cross-Links

• PubChem: 196964
• NPASS: NPC196075
• LOTUS: LTS0097113
• wikiData: Q83038780