Aviculin

Details

• Internal ID: b9b598e3-1c26-40d9-8da2-d85e97e624c9
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3R,4R,5R,6S)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(CC3=CC(=C(C=C3C2C4=CC(=C(C=C4)O)OC)O)OC)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@H]2[C@@H](CC3=CC(=C(C=C3[C@@H]2C4=CC(=C(C=C4)O)OC)O)OC)CO)O)O)O
• InChI: InChI=1S/C26H34O10/c1-12-23(30)24(31)25(32)26(36-12)35-11-17-15(10-27)6-14-8-21(34-3)19(29)9-16(14)22(17)13-4-5-18(28)20(7-13)33-2/h4-5,7-9,12,15,17,22-32H,6,10-11H2,1-3H3/t12-,15-,17-,22-,23-,24+,25+,26+/m0/s1
• InChI Key: FPJFPMQEUVMUKU-CDDCGRQRSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₀
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.21519728 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.87
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• 156765-33-2
• CHEMBL2332673
• DTXSID901045608
• HY-N10481
• CS-0564663
• Q15410250
• (2R,3R,4R,5R,6S)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-methyloxane-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5461	54.61%
Caco-2	-	0.7894	78.94%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5570	55.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8868	88.68%
OATP1B3 inhibitior	+	0.9588	95.88%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6410	64.10%
P-glycoprotein inhibitior	-	0.6072	60.72%
P-glycoprotein substrate	-	0.5424	54.24%
CYP3A4 substrate	+	0.6080	60.80%
CYP2C9 substrate	-	0.7915	79.15%
CYP2D6 substrate	-	0.7682	76.82%
CYP3A4 inhibition	-	0.8845	88.45%
CYP2C9 inhibition	-	0.8487	84.87%
CYP2C19 inhibition	-	0.7730	77.30%
CYP2D6 inhibition	-	0.9155	91.55%
CYP1A2 inhibition	-	0.6768	67.68%
CYP2C8 inhibition	+	0.6532	65.32%
CYP inhibitory promiscuity	-	0.5472	54.72%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6722	67.22%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9420	94.20%
Skin irritation	-	0.8341	83.41%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7263	72.63%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9218	92.18%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8446	84.46%
Acute Oral Toxicity (c)	III	0.6180	61.80%
Estrogen receptor binding	+	0.7430	74.30%
Androgen receptor binding	+	0.5649	56.49%
Thyroid receptor binding	+	0.6170	61.70%
Glucocorticoid receptor binding	+	0.5852	58.52%
Aromatase binding	-	0.5172	51.72%
PPAR gamma	+	0.5355	53.55%
Honey bee toxicity	-	0.8391	83.91%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9110	91.10%

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	99.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.91%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.00%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.60%	92.94%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.47%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.19%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.07%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.74%	89.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.67%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.61%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.59%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.87%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.75%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.45%	94.00%
CHEMBL4208	P20618	Proteasome component C5	85.46%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	83.70%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.47%	92.62%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.18%	82.67%

Plants that contains it

• Acanthophyllum elatius
• Aconitum burnatii
• Barbarea verna
• Boronia coerulescens
• Breynia rostrata
• Breynia vitis-idaea
• Chaenomeles sinensis
• Chenopodium foliosum
• Ilex chinensis
• Iryanthera coriacea
• Mallotus peltatus
• Melochia tomentosa
• Ornithogalum nutans
• Orthocaulis attenuatus
• Polygonum aviculare
• Rubia oncotricha
• Scabiosa pyrenaica
• Scurrula atropurpurea

Cross-Links

• PubChem: 10391477
• NPASS: NPC286245
• ChEMBL: CHEMBL2332673
• LOTUS: LTS0198721
• wikiData: Q15410250