(9R)-9,12-dihydroxy-5-methoxy-2,2,9-trimethyl-8,10-dihydronaphtho[6,7-h]chromen-11-one

Details

• Internal ID: 1687291a-33ac-4faf-830e-c35863ffbba1
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (9R)-9,12-dihydroxy-5-methoxy-2,2,9-trimethyl-8,10-dihydronaphtho[6,7-h]chromen-11-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C3=C(C4=C(CC(CC4=O)(C)O)C=C3C=C2OC)O)C
• SMILES (Isomeric): C[C@]1(CC2=C(C(=O)C1)C(=C3C(=C2)C=C(C4=C3OC(C=C4)(C)C)OC)O)O
• InChI: InChI=1S/C21H22O5/c1-20(2)6-5-13-15(25-4)8-11-7-12-9-21(3,24)10-14(22)16(12)18(23)17(11)19(13)26-20/h5-8,23-24H,9-10H2,1-4H3/t21-/m1/s1
• InChI Key: RUKXXSDGTORZFO-OAQYLSRUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.14672380 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.62
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9854	98.54%
Caco-2	+	0.7841	78.41%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7271	72.71%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.8609	86.09%
OATP1B3 inhibitior	+	0.9788	97.88%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7294	72.94%
P-glycoprotein inhibitior	-	0.6559	65.59%
P-glycoprotein substrate	-	0.5791	57.91%
CYP3A4 substrate	+	0.6283	62.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8230	82.30%
CYP3A4 inhibition	-	0.6859	68.59%
CYP2C9 inhibition	-	0.7666	76.66%
CYP2C19 inhibition	+	0.5829	58.29%
CYP2D6 inhibition	-	0.6525	65.25%
CYP1A2 inhibition	+	0.6481	64.81%
CYP2C8 inhibition	-	0.6096	60.96%
CYP inhibitory promiscuity	-	0.6580	65.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.5629	56.29%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.6504	65.04%
Skin irritation	-	0.7981	79.81%
Skin corrosion	-	0.9554	95.54%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4069	40.69%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5574	55.74%
skin sensitisation	-	0.8366	83.66%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5330	53.30%
Acute Oral Toxicity (c)	III	0.4903	49.03%
Estrogen receptor binding	+	0.8331	83.31%
Androgen receptor binding	+	0.5310	53.10%
Thyroid receptor binding	+	0.6536	65.36%
Glucocorticoid receptor binding	+	0.7341	73.41%
Aromatase binding	+	0.8612	86.12%
PPAR gamma	+	0.8979	89.79%
Honey bee toxicity	-	0.8105	81.05%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	+	0.9599	95.99%

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	99.65%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.07%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.39%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.14%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.71%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.75%	86.33%
CHEMBL4208	P20618	Proteasome component C5	89.85%	90.00%
CHEMBL2581	P07339	Cathepsin D	89.66%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.60%	93.99%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	86.69%	80.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.68%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.50%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.48%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.46%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.33%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.21%	99.23%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	83.12%	98.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.33%	94.42%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.78%	89.50%
CHEMBL2535	P11166	Glucose transporter	81.47%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.04%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.89%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.44%	99.17%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.21%	100.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.12%	99.15%

Plants that contains it

• Cratoxylum cochinchinense
• Cratoxylum sumatranum
• Vismia baccifera
• Vismia japurensis

Cross-Links

• PubChem: 154497676
• LOTUS: LTS0144937
• wikiData: Q105245676