dimethyl (1R,2R,3S,4S)-3,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,2-dicarboxylate

Details

• Internal ID: 240544fe-ebd0-46dd-8afc-ecc83001f4dd
• Taxonomy: Lignans, neolignans and related compounds > Cyclobutane lignans
• IUPAC Name: dimethyl (1R,2R,3S,4S)-3,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,2-dicarboxylate
• SMILES (Canonical): COC(=O)C1C(C(C1C(=O)OC)C2=CC(=C(C=C2)O)O)C3=CC(=C(C=C3)O)O
• SMILES (Isomeric): COC(=O)[C@@H]1[C@H]([C@@H]([C@H]1C(=O)OC)C2=CC(=C(C=C2)O)O)C3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C20H20O8/c1-27-19(25)17-15(9-3-5-11(21)13(23)7-9)16(18(17)20(26)28-2)10-4-6-12(22)14(24)8-10/h3-8,15-18,21-24H,1-2H3/t15-,16-,17+,18+/m0/s1
• InChI Key: LCTBUCCWOZNIKE-WNRNVDISSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₈
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.11581759 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.97
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9491	94.91%
Caco-2	-	0.5586	55.86%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.9194	91.94%
OATP2B1 inhibitior	-	0.5729	57.29%
OATP1B1 inhibitior	+	0.9665	96.65%
OATP1B3 inhibitior	+	0.8571	85.71%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.4892	48.92%
P-glycoprotein inhibitior	-	0.6409	64.09%
P-glycoprotein substrate	-	0.9281	92.81%
CYP3A4 substrate	-	0.5683	56.83%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8256	82.56%
CYP3A4 inhibition	-	0.8999	89.99%
CYP2C9 inhibition	-	0.5786	57.86%
CYP2C19 inhibition	-	0.7111	71.11%
CYP2D6 inhibition	-	0.9037	90.37%
CYP1A2 inhibition	-	0.6497	64.97%
CYP2C8 inhibition	-	0.8480	84.80%
CYP inhibitory promiscuity	-	0.8468	84.68%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7245	72.45%
Carcinogenicity (trinary)	Non-required	0.5634	56.34%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.5320	53.20%
Skin irritation	-	0.7451	74.51%
Skin corrosion	-	0.8955	89.55%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4172	41.72%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9214	92.14%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	+	0.6210	62.10%
Acute Oral Toxicity (c)	III	0.5815	58.15%
Estrogen receptor binding	+	0.6593	65.93%
Androgen receptor binding	+	0.7632	76.32%
Thyroid receptor binding	+	0.6443	64.43%
Glucocorticoid receptor binding	+	0.7216	72.16%
Aromatase binding	-	0.6508	65.08%
PPAR gamma	+	0.5275	52.75%
Honey bee toxicity	-	0.8903	89.03%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9918	99.18%

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	98.16%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.97%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	93.19%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.52%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.15%	85.14%
CHEMBL4208	P20618	Proteasome component C5	83.63%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.53%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.96%	99.15%
CHEMBL2535	P11166	Glucose transporter	81.78%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	81.46%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.57%	99.17%

Plants that contains it

• Vitex quinata

Cross-Links

• PubChem: 163074269
• LOTUS: LTS0038941
• wikiData: Q105149975