Aureothin

Details

• Internal ID: 2c5a6edd-4246-4645-b71d-7dbf657d9e49
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Nitrobenzenes
• IUPAC Name: 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]oxolan-2-yl]pyran-4-one
• SMILES (Canonical): CC1=C(OC(=C(C1=O)C)OC)C2CC(=CC(=CC3=CC=C(C=C3)[N+](=O)[O-])C)CO2
• SMILES (Isomeric): CC1=C(OC(=C(C1=O)C)OC)[C@H]2C/C(=C/C(=C/C3=CC=C(C=C3)[N+](=O)[O-])/C)/CO2
• InChI: InChI=1S/C22H23NO6/c1-13(9-16-5-7-18(8-6-16)23(25)26)10-17-11-19(28-12-17)21-14(2)20(24)15(3)22(27-4)29-21/h5-10,19H,11-12H2,1-4H3/b13-9+,17-10-/t19-/m1/s1
• InChI Key: GQKXCBCSVYJUMI-WACKOAQBSA-N
• Popularity: 44 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₃NO₆
• Molecular Weight: 397.40 g/mol
• Exact Mass: 397.15253745 g/mol
• Topological Polar Surface Area (TPSA): 90.60 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 2825-00-5
• C22H23NO6
• (+)-aureothin
• SCHEMBL13645672
• CHEBI:80024
• DTXSID201043756
• 4H-Pyran-4-one, 2-methoxy-3,5-dimethyl-6-[tetrahydro-4-(.beta.-methyl-p-nitrocinnamylidene)-2-furyl]-
• 4H-Pyran-4-one, 2-methoxy-3,5-dimethyl-6-[tetrahydro-4-[2-methyl-3-(4-nitrophenyl)-2-propenylidene]-2-furanyl]-
• AKOS015969696
• AKOS016023667
• AKOS040756202
• HY-121291
• CS-0081377
• Q27149169
• 2-[(2R)-4-[2-Methyl-3-(4-nitrophenyl)-2-propenylidene]tetrahydrofuran-2beta-yl]-3,5-dimethyl-6-methoxy-4H-pyran-4-one
• 2-Methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]oxolan-2-yl]-4H-pyran-4-one
• 2-methoxy-3,5-dimethyl-6-[(2R,4Z)-4-[(E)-2-methyl-3-(4-nitrophenyl)prop-2-enylidene]tetrahydrofuran-2-yl]pyran-4-one
• 2-methoxy-3,5-dimethyl-6-{(2R,4Z)-4-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran-2-yl}-4H-pyran-4-one
• HQW

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9586	95.86%
Caco-2	+	0.5093	50.93%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6293	62.93%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8650	86.50%
OATP1B3 inhibitior	+	0.9309	93.09%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9729	97.29%
P-glycoprotein inhibitior	+	0.7853	78.53%
P-glycoprotein substrate	-	0.6696	66.96%
CYP3A4 substrate	+	0.6710	67.10%
CYP2C9 substrate	-	0.6075	60.75%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	+	0.7586	75.86%
CYP2C9 inhibition	+	0.5644	56.44%
CYP2C19 inhibition	+	0.7873	78.73%
CYP2D6 inhibition	-	0.8970	89.70%
CYP1A2 inhibition	+	0.5198	51.98%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.9015	90.15%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6828	68.28%
Carcinogenicity (trinary)	Non-required	0.4187	41.87%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.9199	91.99%
Skin irritation	-	0.7926	79.26%
Skin corrosion	-	0.9329	93.29%
Ames mutagenesis	+	0.7730	77.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.4423	44.23%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	+	0.7802	78.02%
skin sensitisation	-	0.8530	85.30%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5550	55.50%
Acute Oral Toxicity (c)	III	0.5879	58.79%
Estrogen receptor binding	+	0.8329	83.29%
Androgen receptor binding	+	0.7579	75.79%
Thyroid receptor binding	+	0.6078	60.78%
Glucocorticoid receptor binding	+	0.8774	87.74%
Aromatase binding	+	0.6608	66.08%
PPAR gamma	+	0.7518	75.18%
Honey bee toxicity	-	0.7610	76.10%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9936	99.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2039	P27338	Monoamine oxidase B	97.73%	92.51%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.70%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.11%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.71%	94.45%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	90.63%	85.30%
CHEMBL1951	P21397	Monoamine oxidase A	90.48%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.09%	91.11%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	90.04%	92.88%
CHEMBL2581	P07339	Cathepsin D	88.53%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.94%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.69%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.28%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.98%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.32%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	80.80%	94.73%

Plants that contains it

• Aglaia spectabilis
• Clibadium pentaneuron
• Coespeletia thyrsiformis f. marcanoi
• Croton bonplandianus
• Croton californicus
• Culcitium canescens
• Cymbopogon nardus
• Dendrobium rotundatum
• Malva verticillata
• Nolina erumpens
• Petasites paradoxus
• Philotheca fitzgeraldii
• Piptolepis leptospermoides
• Ratibida latipalearis
• Toxicodendron succedaneum
• Weddellina squamulosa

Cross-Links

• PubChem: 6569946
• NPASS: NPC85349
• LOTUS: LTS0237251
• wikiData: Q27149169