[(1R,2R,3S,4S)-2-(2,4-dihydroxybenzoyl)-3,4-bis(4-hydroxyphenyl)cyclobutyl]-(2,4-dihydroxyphenyl)methanone

Details

• Internal ID: 3b005a33-7a86-497b-b85b-73f15de60f76
• Taxonomy: Lignans, neolignans and related compounds > Cyclobutane lignans
• IUPAC Name: [(1R,2R,3S,4S)-2-(2,4-dihydroxybenzoyl)-3,4-bis(4-hydroxyphenyl)cyclobutyl]-(2,4-dihydroxyphenyl)methanone
• SMILES (Canonical): C1=CC(=CC=C1C2C(C(C2C(=O)C3=C(C=C(C=C3)O)O)C(=O)C4=C(C=C(C=C4)O)O)C5=CC=C(C=C5)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@H]2[C@@H]([C@H]([C@@H]2C(=O)C3=C(C=C(C=C3)O)O)C(=O)C4=C(C=C(C=C4)O)O)C5=CC=C(C=C5)O)O
• InChI: InChI=1S/C30H24O8/c31-17-5-1-15(2-6-17)25-26(16-3-7-18(32)8-4-16)28(30(38)22-12-10-20(34)14-24(22)36)27(25)29(37)21-11-9-19(33)13-23(21)35/h1-14,25-28,31-36H/t25-,26-,27+,28+/m0/s1
• InChI Key: XHRGIQMCCKSZCH-YVHASNINSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₄O₈
• Molecular Weight: 512.50 g/mol
• Exact Mass: 512.14711772 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.80
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9656	96.56%
Caco-2	-	0.8238	82.38%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8838	88.38%
OATP2B1 inhibitior	-	0.5676	56.76%
OATP1B1 inhibitior	+	0.9122	91.22%
OATP1B3 inhibitior	+	0.7931	79.31%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6668	66.68%
P-glycoprotein inhibitior	-	0.6997	69.97%
P-glycoprotein substrate	-	0.8968	89.68%
CYP3A4 substrate	-	0.6183	61.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8249	82.49%
CYP3A4 inhibition	-	0.5612	56.12%
CYP2C9 inhibition	+	0.7556	75.56%
CYP2C19 inhibition	+	0.6017	60.17%
CYP2D6 inhibition	-	0.8865	88.65%
CYP1A2 inhibition	+	0.5902	59.02%
CYP2C8 inhibition	-	0.6575	65.75%
CYP inhibitory promiscuity	+	0.5109	51.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7219	72.19%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9916	99.16%
Eye irritation	+	0.5712	57.12%
Skin irritation	+	0.5751	57.51%
Skin corrosion	-	0.8183	81.83%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3600	36.00%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.6423	64.23%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.7339	73.39%
Estrogen receptor binding	+	0.7830	78.30%
Androgen receptor binding	+	0.8557	85.57%
Thyroid receptor binding	-	0.5147	51.47%
Glucocorticoid receptor binding	+	0.6995	69.95%
Aromatase binding	-	0.6487	64.87%
PPAR gamma	+	0.7947	79.47%
Honey bee toxicity	-	0.8934	89.34%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9870	98.70%

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	95.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.37%	96.09%
CHEMBL3194	P02766	Transthyretin	86.27%	90.71%
CHEMBL2535	P11166	Glucose transporter	84.69%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.74%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.72%	98.95%

Plants that contains it

• Agapanthus africanus

Cross-Links

• PubChem: 101740969
• LOTUS: LTS0191662
• wikiData: Q105328266