Di-O-Acetylendiandrin A

Details

• Internal ID: 8642ed4e-149e-4e68-b071-0d0f8f61c73e
• Taxonomy: Lignans, neolignans and related compounds > Cyclobutane lignans
• IUPAC Name: [4-[(1R,2R,3S,4S)-2-(4-acetyloxy-3-methoxyphenyl)-3,4-dimethylcyclobutyl]-2-methoxyphenyl] acetate
• SMILES (Canonical): CC1C(C(C1C2=CC(=C(C=C2)OC(=O)C)OC)C3=CC(=C(C=C3)OC(=O)C)OC)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@@H]1C2=CC(=C(C=C2)OC(=O)C)OC)C3=CC(=C(C=C3)OC(=O)C)OC)C
• InChI: InChI=1S/C24H28O6/c1-13-14(2)24(18-8-10-20(30-16(4)26)22(12-18)28-6)23(13)17-7-9-19(29-15(3)25)21(11-17)27-5/h7-14,23-24H,1-6H3/t13-,14-,23-,24-/m0/s1
• InChI Key: VOWJIFKFNBEVKN-NHCASCSRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₆
• Molecular Weight: 412.50 g/mol
• Exact Mass: 412.18858861 g/mol
• Topological Polar Surface Area (TPSA): 71.10 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.71
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• CHEMBL228655
• BDBM50216280

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9896	98.96%
Caco-2	+	0.5906	59.06%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.9074	90.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9263	92.63%
OATP1B3 inhibitior	+	0.9005	90.05%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9283	92.83%
P-glycoprotein inhibitior	+	0.8900	89.00%
P-glycoprotein substrate	-	0.8130	81.30%
CYP3A4 substrate	-	0.5690	56.90%
CYP2C9 substrate	-	0.6180	61.80%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.6747	67.47%
CYP2C9 inhibition	-	0.7501	75.01%
CYP2C19 inhibition	+	0.6084	60.84%
CYP2D6 inhibition	-	0.9483	94.83%
CYP1A2 inhibition	+	0.8066	80.66%
CYP2C8 inhibition	-	0.8081	80.81%
CYP inhibitory promiscuity	-	0.5172	51.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6934	69.34%
Carcinogenicity (trinary)	Non-required	0.4426	44.26%
Eye corrosion	-	0.9777	97.77%
Eye irritation	-	0.8717	87.17%
Skin irritation	-	0.8738	87.38%
Skin corrosion	-	0.9788	97.88%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7921	79.21%
Micronuclear	+	0.5107	51.07%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9557	95.57%
Respiratory toxicity	-	0.8111	81.11%
Reproductive toxicity	+	0.5503	55.03%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	+	0.4600	46.00%
Acute Oral Toxicity (c)	III	0.6333	63.33%
Estrogen receptor binding	+	0.8696	86.96%
Androgen receptor binding	+	0.6498	64.98%
Thyroid receptor binding	+	0.6641	66.41%
Glucocorticoid receptor binding	+	0.7772	77.72%
Aromatase binding	-	0.5334	53.34%
PPAR gamma	+	0.6738	67.38%
Honey bee toxicity	-	0.8191	81.91%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6652	66.52%
Fish aquatic toxicity	+	0.9933	99.33%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2034	P04150	Glucocorticoid receptor	34000 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	96.57%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.83%	85.14%
CHEMBL2581	P07339	Cathepsin D	90.14%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.65%	86.33%
CHEMBL2535	P11166	Glucose transporter	87.19%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.40%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.94%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.98%	89.00%

Plants that contains it

• Endiandra anthropophagorum

Cross-Links

• PubChem: 16756781
• NPASS: NPC470887
• ChEMBL: CHEMBL228655
• LOTUS: LTS0160026
• wikiData: Q105290482