8-[(1S,2R,3S,4R)-2,3-diacetyl-4-(7-methoxy-2-oxochromen-8-yl)cyclobutyl]-7-methoxychromen-2-one

Details

• Internal ID: 6d129267-6cf5-431c-927e-5de3d20f4965
• Taxonomy: Lignans, neolignans and related compounds > Cyclobutane lignans
• IUPAC Name: 8-[(1S,2R,3S,4R)-2,3-diacetyl-4-(7-methoxy-2-oxochromen-8-yl)cyclobutyl]-7-methoxychromen-2-one
• SMILES (Canonical): CC(=O)C1C(C(C1C(=O)C)C2=C(C=CC3=C2OC(=O)C=C3)OC)C4=C(C=CC5=C4OC(=O)C=C5)OC
• SMILES (Isomeric): CC(=O)[C@H]1[C@@H]([C@@H]([C@H]1C(=O)C)C2=C(C=CC3=C2OC(=O)C=C3)OC)C4=C(C=CC5=C4OC(=O)C=C5)OC
• InChI: InChI=1S/C28H24O8/c1-13(29)21-22(14(2)30)26(24-18(34-4)10-6-16-8-12-20(32)36-28(16)24)25(21)23-17(33-3)9-5-15-7-11-19(31)35-27(15)23/h5-12,21-22,25-26H,1-4H3/t21-,22+,25-,26+
• InChI Key: WZTQDHIHDRTWFQ-MNHALERFSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₄O₈
• Molecular Weight: 488.50 g/mol
• Exact Mass: 488.14711772 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 4.21
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9789	97.89%
Caco-2	+	0.4877	48.77%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6906	69.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9525	95.25%
OATP1B3 inhibitior	+	0.9761	97.61%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9409	94.09%
P-glycoprotein inhibitior	+	0.9270	92.70%
P-glycoprotein substrate	-	0.8087	80.87%
CYP3A4 substrate	-	0.5725	57.25%
CYP2C9 substrate	-	0.7922	79.22%
CYP2D6 substrate	-	0.8448	84.48%
CYP3A4 inhibition	-	0.6452	64.52%
CYP2C9 inhibition	-	0.8593	85.93%
CYP2C19 inhibition	-	0.8672	86.72%
CYP2D6 inhibition	-	0.9567	95.67%
CYP1A2 inhibition	+	0.6768	67.68%
CYP2C8 inhibition	-	0.7206	72.06%
CYP inhibitory promiscuity	-	0.5157	51.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.4245	42.45%
Eye corrosion	-	0.9781	97.81%
Eye irritation	-	0.9004	90.04%
Skin irritation	-	0.7934	79.34%
Skin corrosion	-	0.9694	96.94%
Ames mutagenesis	+	0.6063	60.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.8383	83.83%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9441	94.41%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6168	61.68%
Acute Oral Toxicity (c)	II	0.4615	46.15%
Estrogen receptor binding	+	0.8757	87.57%
Androgen receptor binding	+	0.8149	81.49%
Thyroid receptor binding	+	0.5344	53.44%
Glucocorticoid receptor binding	+	0.7976	79.76%
Aromatase binding	-	0.5334	53.34%
PPAR gamma	+	0.6947	69.47%
Honey bee toxicity	-	0.8856	88.56%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6449	64.49%
Fish aquatic toxicity	+	0.9703	97.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.74%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.30%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.77%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.38%	91.11%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.80%	85.30%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.48%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.45%	94.45%

Plants that contains it

• Citrus × aurantium
• Lysimachia arvensis
• Uncaria perrottetii

Cross-Links

• PubChem: 14409177
• NPASS: NPC105749
• LOTUS: LTS0061374
• wikiData: Q104398717