di-O-methylendiandrin A

Details

• Internal ID: e40bdee4-8e01-42b7-b127-99658d4b6b27
• Taxonomy: Lignans, neolignans and related compounds > Cyclobutane lignans
• IUPAC Name: 4-[(1R,2R,3S,4S)-2-(3,4-dimethoxyphenyl)-3,4-dimethylcyclobutyl]-1,2-dimethoxybenzene
• SMILES (Canonical): CC1C(C(C1C2=CC(=C(C=C2)OC)OC)C3=CC(=C(C=C3)OC)OC)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@@H]1C2=CC(=C(C=C2)OC)OC)C3=CC(=C(C=C3)OC)OC)C
• InChI: InChI=1S/C22H28O4/c1-13-14(2)22(16-8-10-18(24-4)20(12-16)26-6)21(13)15-7-9-17(23-3)19(11-15)25-5/h7-14,21-22H,1-6H3/t13-,14-,21-,22-/m0/s1
• InChI Key: IOTXFXWARGNLEJ-WJWAULOUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₄
• Molecular Weight: 356.50 g/mol
• Exact Mass: 356.19875937 g/mol
• Topological Polar Surface Area (TPSA): 36.90 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.87
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• CHEMBL388363
• D0PR2T
• BDBM50216279

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.8911	89.11%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8746	87.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9348	93.48%
OATP1B3 inhibitior	+	0.9567	95.67%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7645	76.45%
P-glycoprotein inhibitior	+	0.7585	75.85%
P-glycoprotein substrate	-	0.8047	80.47%
CYP3A4 substrate	-	0.6408	64.08%
CYP2C9 substrate	-	0.5665	56.65%
CYP2D6 substrate	+	0.3822	38.22%
CYP3A4 inhibition	+	0.6144	61.44%
CYP2C9 inhibition	-	0.7970	79.70%
CYP2C19 inhibition	+	0.8604	86.04%
CYP2D6 inhibition	-	0.9384	93.84%
CYP1A2 inhibition	+	0.7773	77.73%
CYP2C8 inhibition	-	0.8141	81.41%
CYP inhibitory promiscuity	+	0.8165	81.65%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7267	72.67%
Carcinogenicity (trinary)	Non-required	0.4039	40.39%
Eye corrosion	-	0.9644	96.44%
Eye irritation	-	0.8522	85.22%
Skin irritation	-	0.8428	84.28%
Skin corrosion	-	0.9806	98.06%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9008	90.08%
Micronuclear	-	0.6167	61.67%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.9073	90.73%
Respiratory toxicity	-	0.7889	78.89%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	-	0.5894	58.94%
Acute Oral Toxicity (c)	III	0.6563	65.63%
Estrogen receptor binding	+	0.7997	79.97%
Androgen receptor binding	+	0.6238	62.38%
Thyroid receptor binding	+	0.7733	77.33%
Glucocorticoid receptor binding	+	0.6033	60.33%
Aromatase binding	+	0.5208	52.08%
PPAR gamma	+	0.6342	63.42%
Honey bee toxicity	-	0.9167	91.67%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.9754	97.54%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2034	P04150	Glucocorticoid receptor	13000 nM	IC50	PMID: 19581457

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.83%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.25%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.72%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.70%	86.33%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	86.04%	96.86%
CHEMBL2535	P11166	Glucose transporter	84.03%	98.75%
CHEMBL2581	P07339	Cathepsin D	83.57%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.64%	95.89%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.44%	94.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.10%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.95%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.43%	97.14%

Plants that contains it

• Endiandra anthropophagorum

Cross-Links

• PubChem: 16756782
• NPASS: NPC473264
• ChEMBL: CHEMBL388363
• LOTUS: LTS0239049
• wikiData: Q105116881