avenacin B-1

Details

• Internal ID: 9f513cb4-6b39-430d-86cb-d19f10654c30
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1S,3R,5R,6R,9S,11R,14R,15S,17S,18S,20S,21R,23R)-21-formyl-17-hydroxy-9-[(2S,3R,4S,5S)-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-6,10,10,14,15,18,21-heptamethyl-2-oxahexacyclo[13.8.0.01,3.05,14.06,11.018,23]tricosan-20-yl] 2-(methylamino)benzoate
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1OC4C(C(C(CO4)OC5C(C(C(C(O5)CO)O)O)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)CC7C8(C3(CC(C9(C8CC(C(C9)OC(=O)C1=CC=CC=C1NC)(C)C=O)C)O)C)O7)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2C[C@@H]4[C@]5([C@]3(C[C@@H]([C@@]6([C@H]5C[C@@]([C@H](C6)OC(=O)C7=CC=CC=C7NC)(C)C=O)C)O)C)O4)C)(C)C)O[C@H]8[C@@H]([C@H]([C@H](CO8)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C55H83NO20/c1-49(2)30-13-16-53(6)31(17-35-55(76-35)32-18-50(3,24-59)36(20-52(32,5)33(60)19-54(53,55)7)73-45(68)25-11-9-10-12-26(25)56-8)51(30,4)15-14-34(49)74-48-44(75-47-43(67)41(65)38(62)28(22-58)71-47)39(63)29(23-69-48)72-46-42(66)40(64)37(61)27(21-57)70-46/h9-12,24,27-44,46-48,56-58,60-67H,13-23H2,1-8H3/t27-,28-,29+,30+,31-,32-,33+,34+,35-,36+,37-,38-,39+,40+,41+,42-,43-,44-,46+,47+,48+,50+,51+,52+,53-,54+,55-/m1/s1
• InChI Key: YYSBRPJSMBHDDU-GDMCUCSUSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₈₃NO₂₀
• Molecular Weight: 1078.20 g/mol
• Exact Mass: 1077.55084404 g/mol
• Topological Polar Surface Area (TPSA): 326.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 21
• H-Bond Donor: 11
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6061	60.61%
Caco-2	-	0.8682	86.82%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Nucleus	0.3887	38.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7722	77.22%
OATP1B3 inhibitior	+	0.9062	90.62%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9545	95.45%
P-glycoprotein inhibitior	+	0.7457	74.57%
P-glycoprotein substrate	+	0.6660	66.60%
CYP3A4 substrate	+	0.7574	75.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8480	84.80%
CYP3A4 inhibition	-	0.6935	69.35%
CYP2C9 inhibition	-	0.8121	81.21%
CYP2C19 inhibition	-	0.7939	79.39%
CYP2D6 inhibition	-	0.9198	91.98%
CYP1A2 inhibition	-	0.8037	80.37%
CYP2C8 inhibition	+	0.8281	82.81%
CYP inhibitory promiscuity	-	0.9439	94.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6394	63.94%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.8994	89.94%
Skin irritation	-	0.7726	77.26%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7375	73.75%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.7237	72.37%
skin sensitisation	-	0.8679	86.79%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.4773	47.73%
Acute Oral Toxicity (c)	III	0.6175	61.75%
Estrogen receptor binding	+	0.7540	75.40%
Androgen receptor binding	+	0.7622	76.22%
Thyroid receptor binding	+	0.5960	59.60%
Glucocorticoid receptor binding	+	0.7629	76.29%
Aromatase binding	+	0.6372	63.72%
PPAR gamma	+	0.7893	78.93%
Honey bee toxicity	-	0.6070	60.70%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9202	92.02%

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	98.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.38%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	95.90%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.49%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.47%	98.95%
CHEMBL5028	O14672	ADAM10	92.63%	97.50%
CHEMBL226	P30542	Adenosine A1 receptor	90.94%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.90%	91.24%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.47%	96.61%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.38%	95.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.88%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.91%	86.33%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	87.69%	97.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.13%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.82%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.69%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.44%	95.89%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	84.69%	89.44%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.29%	92.88%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.40%	94.08%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.41%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.46%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.06%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.91%	95.83%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.78%	85.83%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.61%	91.07%

Plants that contains it

• Avena sativa
• Avena sterilis

Cross-Links

• PubChem: 90657695
• LOTUS: LTS0221117
• wikiData: Q104395964