Pyranochromene

Details

• Internal ID: 65dde250-a7b4-4904-9c57-7ec741c7dd35
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: (2R,3R,8R,10S)-2-(3,4-dihydroxyphenyl)-10-methyl-2,3,4,8,9,10-hexahydropyrano[2,3-f]chromene-3,5,8-triol
• SMILES (Canonical): CC1CC(OC2=C1C3=C(CC(C(O3)C4=CC(=C(C=C4)O)O)O)C(=C2)O)O
• SMILES (Isomeric): C[C@H]1C[C@@H](OC2=C1C3=C(C[C@H]([C@H](O3)C4=CC(=C(C=C4)O)O)O)C(=C2)O)O
• InChI: InChI=1S/C19H20O7/c1-8-4-16(24)25-15-7-12(21)10-6-14(23)18(26-19(10)17(8)15)9-2-3-11(20)13(22)5-9/h2-3,5,7-8,14,16,18,20-24H,4,6H2,1H3/t8-,14+,16+,18+/m0/s1
• InChI Key: KLFQXCVGEVYPOF-PCPPRTPOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₇
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.12090297 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• CHEBI:193263
• LMPK12020088
• (2R,3R,8R,10S)-2-(3,4-dihydroxyphenyl)-10-methyl-2,3,4,8,9,10-hexahydropyrano[2,3-]chromene-3,5,8-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9271	92.71%
Caco-2	-	0.5705	57.05%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6649	66.49%
OATP2B1 inhibitior	-	0.5780	57.80%
OATP1B1 inhibitior	+	0.9211	92.11%
OATP1B3 inhibitior	+	0.9403	94.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6853	68.53%
P-glycoprotein inhibitior	-	0.8097	80.97%
P-glycoprotein substrate	-	0.7308	73.08%
CYP3A4 substrate	+	0.5658	56.58%
CYP2C9 substrate	+	0.6104	61.04%
CYP2D6 substrate	+	0.3798	37.98%
CYP3A4 inhibition	-	0.9716	97.16%
CYP2C9 inhibition	-	0.8707	87.07%
CYP2C19 inhibition	-	0.8785	87.85%
CYP2D6 inhibition	-	0.9420	94.20%
CYP1A2 inhibition	-	0.8526	85.26%
CYP2C8 inhibition	-	0.6174	61.74%
CYP inhibitory promiscuity	-	0.9550	95.50%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5355	53.55%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8487	84.87%
Skin irritation	-	0.6776	67.76%
Skin corrosion	-	0.9299	92.99%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3736	37.36%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8482	84.82%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8126	81.26%
Acute Oral Toxicity (c)	III	0.4412	44.12%
Estrogen receptor binding	+	0.5839	58.39%
Androgen receptor binding	+	0.7000	70.00%
Thyroid receptor binding	+	0.6810	68.10%
Glucocorticoid receptor binding	+	0.6681	66.81%
Aromatase binding	-	0.5393	53.93%
PPAR gamma	-	0.5487	54.87%
Honey bee toxicity	-	0.8292	82.92%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9156	91.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.23%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.86%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.00%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	91.84%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.95%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.54%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.59%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.97%	86.33%
CHEMBL2581	P07339	Cathepsin D	83.76%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.81%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	80.75%	94.73%

Plants that contains it

• Lupinus angustifolius

Cross-Links

• PubChem: 44257104
• LOTUS: LTS0018559
• wikiData: Q105142589