Lespecyrtin A1

Details

• Internal ID: 0b58d7f6-5e38-4fb4-8b7d-35bfe1f688a6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2R,3R)-3,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC2=C1OC(C(C2=O)O)C3=CC=C(C=C3)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC2=C1O[C@@H]([C@H](C2=O)O)C3=CC=C(C=C3)O)O)C
• InChI: InChI=1S/C20H20O5/c1-11(2)3-8-14-16(22)10-9-15-17(23)18(24)19(25-20(14)15)12-4-6-13(21)7-5-12/h3-7,9-10,18-19,21-22,24H,8H2,1-2H3/t18-,19+/m0/s1
• InChI Key: KZFZDYGSHDBMJU-RBUKOAKNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• CHEMBL556682

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	+	0.6200	62.00%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7724	77.24%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.7610	76.10%
OATP1B3 inhibitior	+	0.9450	94.50%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7995	79.95%
P-glycoprotein inhibitior	-	0.5681	56.81%
P-glycoprotein substrate	-	0.8370	83.70%
CYP3A4 substrate	+	0.5525	55.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7126	71.26%
CYP3A4 inhibition	-	0.7662	76.62%
CYP2C9 inhibition	+	0.9706	97.06%
CYP2C19 inhibition	+	0.9321	93.21%
CYP2D6 inhibition	-	0.6989	69.89%
CYP1A2 inhibition	+	0.7947	79.47%
CYP2C8 inhibition	-	0.6486	64.86%
CYP inhibitory promiscuity	+	0.9093	90.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6933	69.33%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.5708	57.08%
Skin irritation	-	0.7099	70.99%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6048	60.48%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.7156	71.56%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7463	74.63%
Acute Oral Toxicity (c)	III	0.6445	64.45%
Estrogen receptor binding	+	0.8216	82.16%
Androgen receptor binding	+	0.6889	68.89%
Thyroid receptor binding	+	0.6495	64.95%
Glucocorticoid receptor binding	+	0.7734	77.34%
Aromatase binding	+	0.5433	54.33%
PPAR gamma	+	0.7893	78.93%
Honey bee toxicity	-	0.8530	85.30%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	99.53%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.49%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.60%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.00%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.54%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.78%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.59%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.12%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.70%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.81%	86.33%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.10%	91.38%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.42%	93.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.12%	99.17%

Plants that contains it

• Lespedeza cyrtobotrya
• Teucrium betonicum

Cross-Links

• PubChem: 25208280
• NPASS: NPC112158
• LOTUS: LTS0201189
• wikiData: Q105148128