Austrobailignan 5

Details

• Internal ID: ff826bac-0975-4a61-a876-ce21c58f8c11
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 5-[(2R,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-1,3-benzodioxole
• SMILES (Canonical): CC(CC1=CC2=C(C=C1)OCO2)C(C)CC3=CC4=C(C=C3)OCO4
• SMILES (Isomeric): C[C@H](CC1=CC2=C(C=C1)OCO2)[C@H](C)CC3=CC4=C(C=C3)OCO4
• InChI: InChI=1S/C20H22O4/c1-13(7-15-3-5-17-19(9-15)23-11-21-17)14(2)8-16-4-6-18-20(10-16)24-12-22-18/h3-6,9-10,13-14H,7-8,11-12H2,1-2H3/t13-,14-/m1/s1
• InChI Key: QEFJURUMSHPMTC-ZIAGYGMSSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.15180918 g/mol
• Topological Polar Surface Area (TPSA): 36.90 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.20
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 55890-23-8
• CHEMBL400319
• DTXSID30971294
• 5,5'-(2,3-Dimethylbutane-1,4-diyl)bis(2H-1,3-benzodioxole)
• 1,3-Benzodioxole, 5,5'-((2R,3R)-2,3-dimethyl-1,4-butanediyl)bis-
• 5-[(2R,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethyl-butyl]-1,3-benzodioxole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	+	0.8363	83.63%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6018	60.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9563	95.63%
OATP1B3 inhibitior	+	0.9303	93.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8657	86.57%
P-glycoprotein inhibitior	+	0.7358	73.58%
P-glycoprotein substrate	-	0.9512	95.12%
CYP3A4 substrate	-	0.7596	75.96%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	+	0.3563	35.63%
CYP3A4 inhibition	+	0.8591	85.91%
CYP2C9 inhibition	+	0.8282	82.82%
CYP2C19 inhibition	+	0.8660	86.60%
CYP2D6 inhibition	+	0.8227	82.27%
CYP1A2 inhibition	+	0.8827	88.27%
CYP2C8 inhibition	-	0.9747	97.47%
CYP inhibitory promiscuity	+	0.8738	87.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Warning	0.4118	41.18%
Eye corrosion	-	0.9811	98.11%
Eye irritation	-	0.7380	73.80%
Skin irritation	-	0.6782	67.82%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9161	91.61%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.5443	54.43%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6876	68.76%
Acute Oral Toxicity (c)	III	0.8117	81.17%
Estrogen receptor binding	+	0.7586	75.86%
Androgen receptor binding	+	0.7316	73.16%
Thyroid receptor binding	-	0.5186	51.86%
Glucocorticoid receptor binding	+	0.5675	56.75%
Aromatase binding	-	0.4903	49.03%
PPAR gamma	+	0.7281	72.81%
Honey bee toxicity	-	0.9385	93.85%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9947	99.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.95%	96.77%
CHEMBL2581	P07339	Cathepsin D	96.76%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.15%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.86%	94.45%
CHEMBL3492	P49721	Proteasome Macropain subunit	91.42%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.66%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.38%	91.11%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	87.22%	85.30%
CHEMBL2039	P27338	Monoamine oxidase B	86.86%	92.51%
CHEMBL3401	O75469	Pregnane X receptor	85.88%	94.73%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	84.80%	80.96%
CHEMBL4208	P20618	Proteasome component C5	83.38%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.36%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.15%	95.89%
CHEMBL3837	P07711	Cathepsin L	80.14%	96.61%

Plants that contains it

• Austrobaileya scandens
• Casuarina equisetifolia
• Catalpa bignonioides
• Cirsium arvense var. integrifolium
• Entada phaseoloides
• Erymophyllum tenellum
• Esenbeckia nesiotica
• Hyptis tomentosa
• Ipomoea cristulata
• Magnolia ovata
• Mollugo pentaphylla
• Myristica fragrans
• Nothofagus menziesii
• Pancratium trianthum
• Piper pedicellosum
• Rhodotypos scandens
• Saururus cernuus
• Xanthostemon oppositifolius

Cross-Links

• PubChem: 185825
• NPASS: NPC80241
• LOTUS: LTS0090134
• wikiData: Q82954753