(2S)-5-hydroxy-2-(7-methoxy-2,2-dimethylchromen-6-yl)-6,8,8-trimethyl-2,3-dihydropyrano[2,3-h]chromen-4-one

Details

• Internal ID: 0aad3269-18e2-4a3f-b611-a8e0f6aca90f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Pyranoflavonoids
• IUPAC Name: (2S)-5-hydroxy-2-(7-methoxy-2,2-dimethylchromen-6-yl)-6,8,8-trimethyl-2,3-dihydropyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC1=C(C2=C(C3=C1OC(C=C3)(C)C)OC(CC2=O)C4=C(C=C5C(=C4)C=CC(O5)(C)C)OC)O
• SMILES (Isomeric): CC1=C(C2=C(C3=C1OC(C=C3)(C)C)O[C@@H](CC2=O)C4=C(C=C5C(=C4)C=CC(O5)(C)C)OC)O
• InChI: InChI=1S/C27H28O6/c1-14-23(29)22-18(28)12-21(31-25(22)16-8-10-27(4,5)33-24(14)16)17-11-15-7-9-26(2,3)32-19(15)13-20(17)30-6/h7-11,13,21,29H,12H2,1-6H3/t21-/m0/s1
• InChI Key: KGHCSILZCRZWKU-NRFANRHFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₆
• Molecular Weight: 448.50 g/mol
• Exact Mass: 448.18858861 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.78
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9845	98.45%
Caco-2	+	0.5880	58.80%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8348	83.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8539	85.39%
OATP1B3 inhibitior	+	0.9824	98.24%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9740	97.40%
P-glycoprotein inhibitior	+	0.8523	85.23%
P-glycoprotein substrate	+	0.5294	52.94%
CYP3A4 substrate	+	0.6659	66.59%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8063	80.63%
CYP3A4 inhibition	+	0.7039	70.39%
CYP2C9 inhibition	-	0.5660	56.60%
CYP2C19 inhibition	+	0.8398	83.98%
CYP2D6 inhibition	-	0.7063	70.63%
CYP1A2 inhibition	-	0.5810	58.10%
CYP2C8 inhibition	+	0.6624	66.24%
CYP inhibitory promiscuity	+	0.6660	66.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Danger	0.5034	50.34%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.7474	74.74%
Skin irritation	-	0.7859	78.59%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4219	42.19%
Micronuclear	+	0.5959	59.59%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8803	88.03%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6982	69.82%
Acute Oral Toxicity (c)	III	0.4392	43.92%
Estrogen receptor binding	+	0.9105	91.05%
Androgen receptor binding	+	0.6154	61.54%
Thyroid receptor binding	+	0.7146	71.46%
Glucocorticoid receptor binding	+	0.7745	77.45%
Aromatase binding	+	0.5506	55.06%
PPAR gamma	+	0.8384	83.84%
Honey bee toxicity	-	0.7647	76.47%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9457	94.57%

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	98.61%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.77%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.55%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.29%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.27%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.37%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.97%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.56%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.37%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.17%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.55%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.43%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.71%	95.89%
CHEMBL4208	P20618	Proteasome component C5	84.55%	90.00%
CHEMBL2535	P11166	Glucose transporter	84.42%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.27%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.01%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.23%	96.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.13%	89.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.04%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	81.81%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.40%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.14%	92.94%

Plants that contains it

• Lespedeza virgata

Cross-Links

• PubChem: 44444183
• LOTUS: LTS0187977
• wikiData: Q105140774