Lespecyrtin B2

Details

• Internal ID: 3a9ea2a6-9438-4604-ae11-46bc6e86507d
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: (E)-1-(5-hydroxy-2,2-dimethylchromen-8-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): CC1(C=CC2=C(C=CC(=C2O1)C(=O)C=CC3=CC=C(C=C3)O)O)C
• SMILES (Isomeric): CC1(C=CC2=C(C=CC(=C2O1)C(=O)/C=C/C3=CC=C(C=C3)O)O)C
• InChI: InChI=1S/C20H18O4/c1-20(2)12-11-16-18(23)10-8-15(19(16)24-20)17(22)9-5-13-3-6-14(21)7-4-13/h3-12,21,23H,1-2H3/b9-5+
• InChI Key: YXOJEXDPGBEHQJ-WEVVVXLNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₄
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.18
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• CHEMBL559972

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	+	0.6466	64.66%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7916	79.16%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.9021	90.21%
OATP1B3 inhibitior	+	0.9883	98.83%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.7847	78.47%
P-glycoprotein inhibitior	-	0.5652	56.52%
P-glycoprotein substrate	-	0.8014	80.14%
CYP3A4 substrate	+	0.5356	53.56%
CYP2C9 substrate	-	0.7895	78.95%
CYP2D6 substrate	-	0.8143	81.43%
CYP3A4 inhibition	+	0.5216	52.16%
CYP2C9 inhibition	+	0.7765	77.65%
CYP2C19 inhibition	+	0.6474	64.74%
CYP2D6 inhibition	-	0.7660	76.60%
CYP1A2 inhibition	+	0.7890	78.90%
CYP2C8 inhibition	+	0.6261	62.61%
CYP inhibitory promiscuity	+	0.6395	63.95%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9713	97.13%
Carcinogenicity (trinary)	Non-required	0.6007	60.07%
Eye corrosion	-	0.9854	98.54%
Eye irritation	+	0.6672	66.72%
Skin irritation	-	0.6891	68.91%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4915	49.15%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.7509	75.09%
skin sensitisation	-	0.7468	74.68%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.6425	64.25%
Acute Oral Toxicity (c)	III	0.7412	74.12%
Estrogen receptor binding	+	0.9713	97.13%
Androgen receptor binding	+	0.8456	84.56%
Thyroid receptor binding	+	0.8499	84.99%
Glucocorticoid receptor binding	+	0.8836	88.36%
Aromatase binding	+	0.8219	82.19%
PPAR gamma	+	0.7944	79.44%
Honey bee toxicity	-	0.8837	88.37%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9699	96.99%

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	98.05%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.64%	94.45%
CHEMBL242	Q92731	Estrogen receptor beta	89.16%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.91%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.56%	95.56%
CHEMBL3194	P02766	Transthyretin	87.03%	90.71%
CHEMBL4208	P20618	Proteasome component C5	87.01%	90.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.68%	93.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.56%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.30%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	84.38%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.04%	95.50%
CHEMBL1951	P21397	Monoamine oxidase A	80.78%	91.49%

Plants that contains it

• Lespedeza cyrtobotrya
• Teucrium betonicum

Cross-Links

• PubChem: 25208602
• NPASS: NPC64908
• ChEMBL: CHEMBL559972
• LOTUS: LTS0263080
• wikiData: Q105367995