(2R,3R)-Lespedezaflavanone C

Details

• Internal ID: afc0536a-bb3d-4e75-ba27-0ff38fd5eafe
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2R,3R)-3,5,7-trihydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1)C2C(C(=O)C3=C(C=C(C(=C3O2)CC=C(C)C)O)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1)[C@@H]2[C@H](C(=O)C3=C(C=C(C(=C3O2)CC=C(C)C)O)O)O)O)C
• InChI: InChI=1S/C25H28O6/c1-13(2)5-7-15-11-16(8-10-18(15)26)24-23(30)22(29)21-20(28)12-19(27)17(25(21)31-24)9-6-14(3)4/h5-6,8,10-12,23-24,26-28,30H,7,9H2,1-4H3/t23-,24+/m0/s1
• InChI Key: WFHBGCVPESHDKZ-BJKOFHAPSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₆
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.18858861 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 4.50
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• (2R,3R)-lespedezaflavanone C
• CHEMBL463256
• SCHEMBL7052282

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9877	98.77%
Caco-2	+	0.5901	59.01%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5872	58.72%
OATP2B1 inhibitior	-	0.7090	70.90%
OATP1B1 inhibitior	+	0.9039	90.39%
OATP1B3 inhibitior	+	0.9063	90.63%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8859	88.59%
P-glycoprotein inhibitior	+	0.6927	69.27%
P-glycoprotein substrate	-	0.8510	85.10%
CYP3A4 substrate	+	0.5291	52.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7858	78.58%
CYP3A4 inhibition	-	0.7076	70.76%
CYP2C9 inhibition	+	0.9149	91.49%
CYP2C19 inhibition	+	0.8913	89.13%
CYP2D6 inhibition	-	0.7176	71.76%
CYP1A2 inhibition	+	0.8226	82.26%
CYP2C8 inhibition	-	0.7069	70.69%
CYP inhibitory promiscuity	+	0.9161	91.61%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6851	68.51%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.6294	62.94%
Skin irritation	-	0.7171	71.71%
Skin corrosion	-	0.9318	93.18%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7271	72.71%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.7344	73.44%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5582	55.82%
Acute Oral Toxicity (c)	III	0.6443	64.43%
Estrogen receptor binding	+	0.9257	92.57%
Androgen receptor binding	+	0.7472	74.72%
Thyroid receptor binding	+	0.6741	67.41%
Glucocorticoid receptor binding	+	0.8420	84.20%
Aromatase binding	+	0.6005	60.05%
PPAR gamma	+	0.8421	84.21%
Honey bee toxicity	-	0.8743	87.43%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9925	99.25%

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	99.07%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.57%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	95.76%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.91%	85.14%
CHEMBL2581	P07339	Cathepsin D	91.22%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.75%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.83%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.83%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.38%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.27%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.61%	99.15%

Plants that contains it

• Broussonetia papyrifera
• Euchresta japonica
• Lespedeza davidii

Cross-Links

• PubChem: 14542252
• NPASS: NPC278476
• LOTUS: LTS0206386
• wikiData: Q104401972