Alternariol monomethyl ether

Details

• Internal ID: 735fbfa6-2d65-4a74-81d3-4b980dd89eb7
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one
• SMILES (Canonical): CC1=CC(=CC2=C1C3=C(C(=CC(=C3)OC)O)C(=O)O2)O
• SMILES (Isomeric): CC1=CC(=CC2=C1C3=C(C(=CC(=C3)OC)O)C(=O)O2)O
• InChI: InChI=1S/C15H12O5/c1-7-3-8(16)4-12-13(7)10-5-9(19-2)6-11(17)14(10)15(18)20-12/h3-6,16-17H,1-2H3
• InChI Key: LCSDQFNUYFTXMT-UHFFFAOYSA-N
• Popularity: 132 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25 g/mol
• Exact Mass: 272.06847348 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 23452-05-3
• Djalonensone
• 26894-49-5
• Alternariol-9-methyl ether
• Alternariol monomethylether
• alternariol 5-O-methyl ether
• Alternariol methyl ether
• 3,7-Dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one
• CCRIS 2898
• 3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one
• 3,7-Dihydroxy-9-methoxy-1-methyl-6H-dibenzo(b,d)pyran-6-one
• BRN 0253553
• UNII-Y79STA800H
• CHEMBL483526
• Y79STA800H
• 6H-DIBENZO(b,d)PYRAN-6-ONE, 3,7-DIHYDROXY-9-METHOXY-1-METHYL-
• NSC638262
• Alternariol monomethyl ether from Alternaria alternata (tenuis)
• 5-18-04-00517 (Beilstein Handbook Reference)
• alternariol 9-methyl ether
• 2-Biphenylcarboxylic acid, 2',3',4'-trihydroxy-5-methoxy-6'-methyl-, delta-lactone
• 6H-Dibenzo[b,d]pyran-6-one, 3,7(3,9 or 7,9)-dihydroxy-9(7 or 3)-methoxy-1-methyl-
• 3,7-Dihydroxy-9-methoxy-1-methyl-6H-dibenzo[b,d]pyran-6-one
• alternariol5-O-methylether
• Alternariol 9-O-methyl ether
• MLS004711973
• Dexamfetamine-d3 Hydrochloride
• MEGxm0_000058
• DTXSID30178004
• CHEBI:141315
• LCSDQFNUYFTXMT-UHFFFAOYSA-N
• BDBM50276157
• MFCD00058532
• AKOS027295171
• 1ST7257
• BS-1261
• CS-W014579
• HY-W013863
• NSC-638262
• Alternariol monomethyl ether, Djalonensone
• LS-61187
• SMR003474896
• FT-0661537
• Alternariol-9-methyl ether, analytical standard
• J-016590
• Q27294342
• 3,7-dihydroxy-9-methoxy-1-methyl-benzo[c]chromen-6-one
• 3,7-Dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one #
• 2-Biphenylcarboxylic acid, 2',3',4'-trihydroxy-5-methoxy-6'-methyl-, delta-lactone (6CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9628	96.28%
Caco-2	+	0.8276	82.76%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7098	70.98%
OATP2B1 inhibitior	-	0.7114	71.14%
OATP1B1 inhibitior	+	0.9386	93.86%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7239	72.39%
P-glycoprotein inhibitior	-	0.7788	77.88%
P-glycoprotein substrate	-	0.8809	88.09%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.5374	53.74%
CYP2D6 substrate	-	0.8728	87.28%
CYP3A4 inhibition	-	0.6130	61.30%
CYP2C9 inhibition	-	0.6826	68.26%
CYP2C19 inhibition	-	0.7757	77.57%
CYP2D6 inhibition	-	0.7791	77.91%
CYP1A2 inhibition	+	0.7566	75.66%
CYP2C8 inhibition	-	0.7365	73.65%
CYP inhibitory promiscuity	-	0.6169	61.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9213	92.13%
Carcinogenicity (trinary)	Non-required	0.5621	56.21%
Eye corrosion	-	0.9452	94.52%
Eye irritation	+	0.9390	93.90%
Skin irritation	-	0.7062	70.62%
Skin corrosion	-	0.9862	98.62%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6646	66.46%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9628	96.28%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6205	62.05%
Acute Oral Toxicity (c)	III	0.6580	65.80%
Estrogen receptor binding	+	0.7860	78.60%
Androgen receptor binding	+	0.7225	72.25%
Thyroid receptor binding	+	0.5388	53.88%
Glucocorticoid receptor binding	+	0.8633	86.33%
Aromatase binding	+	0.7408	74.08%
PPAR gamma	+	0.7450	74.50%
Honey bee toxicity	-	0.8528	85.28%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8588	85.88%

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	98.73%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.08%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.62%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.49%	99.15%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	93.25%	93.65%
CHEMBL3401	O75469	Pregnane X receptor	91.70%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.75%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.14%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	86.49%	91.49%
CHEMBL2581	P07339	Cathepsin D	85.46%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.81%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.54%	99.17%
CHEMBL2535	P11166	Glucose transporter	82.15%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.36%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.68%	94.42%
CHEMBL4581	P52732	Kinesin-like protein 1	80.38%	93.18%

Plants that contains it

• Anthocleista djalonensis
• Citrus × aurantium
• Inula helenium
• Pinellia pedatisecta
• Sonneratia alba
• Sorghum bicolor

Cross-Links

• PubChem: 5360741
• NPASS: NPC267509
• LOTUS: LTS0256015
• wikiData: Q27294342