(4R,5R)-5-hydroxy-10,10,16,16-tetramethyl-4-phenyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),8(13),11,17-pentaen-6-one

Details

• Internal ID: eca07d6f-aea4-4896-9fc7-1a38a6a72158
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Pyranoflavonoids
• IUPAC Name: (4R,5R)-5-hydroxy-10,10,16,16-tetramethyl-4-phenyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),8(13),11,17-pentaen-6-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C3=C(C4=C2OC(C(C4=O)O)C5=CC=CC=C5)OC(C=C3)(C)C)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C3=C(C4=C2O[C@@H]([C@H](C4=O)O)C5=CC=CC=C5)OC(C=C3)(C)C)C
• InChI: InChI=1S/C25H24O5/c1-24(2)12-10-15-21(29-24)16-11-13-25(3,4)30-23(16)17-18(26)19(27)20(28-22(15)17)14-8-6-5-7-9-14/h5-13,19-20,27H,1-4H3/t19-,20+/m0/s1
• InChI Key: ZZNMWGVMOBOREI-VQTJNVASSA-N
• Popularity: 197 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₅
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.16237386 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.73
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• CHEMBL464952

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	+	0.5743	57.43%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8013	80.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8883	88.83%
OATP1B3 inhibitior	+	0.9777	97.77%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9060	90.60%
P-glycoprotein inhibitior	+	0.7972	79.72%
P-glycoprotein substrate	-	0.8708	87.08%
CYP3A4 substrate	+	0.5428	54.28%
CYP2C9 substrate	-	0.6029	60.29%
CYP2D6 substrate	-	0.7722	77.22%
CYP3A4 inhibition	+	0.5982	59.82%
CYP2C9 inhibition	-	0.5293	52.93%
CYP2C19 inhibition	+	0.6309	63.09%
CYP2D6 inhibition	-	0.9096	90.96%
CYP1A2 inhibition	-	0.5445	54.45%
CYP2C8 inhibition	-	0.7076	70.76%
CYP inhibitory promiscuity	+	0.5508	55.08%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4503	45.03%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.6528	65.28%
Skin irritation	-	0.7000	70.00%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7349	73.49%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	+	0.6301	63.01%
skin sensitisation	-	0.7965	79.65%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6884	68.84%
Acute Oral Toxicity (c)	III	0.6106	61.06%
Estrogen receptor binding	+	0.8730	87.30%
Androgen receptor binding	+	0.6131	61.31%
Thyroid receptor binding	+	0.7704	77.04%
Glucocorticoid receptor binding	+	0.8535	85.35%
Aromatase binding	+	0.6034	60.34%
PPAR gamma	+	0.7951	79.51%
Honey bee toxicity	-	0.9153	91.53%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9777	97.77%

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	95.12%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	93.08%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.37%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.75%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.32%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.98%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.70%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.24%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.87%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.74%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	83.61%	91.49%
CHEMBL5028	O14672	ADAM10	80.12%	97.50%

Plants that contains it

• Patrinia scabra

Cross-Links

• PubChem: 15426600
• NPASS: NPC88983