Alternariol

Details

• Internal ID: d80cf7cc-2c2b-49a3-8a31-5e1d8fa2c0a8
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one
• SMILES (Canonical): CC1=CC(=CC2=C1C3=C(C(=CC(=C3)O)O)C(=O)O2)O
• SMILES (Isomeric): CC1=CC(=CC2=C1C3=C(C(=CC(=C3)O)O)C(=O)O2)O
• InChI: InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3
• InChI Key: CEBXXEKPIIDJHL-UHFFFAOYSA-N
• Popularity: 722 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₅
• Molecular Weight: 258.23 g/mol
• Exact Mass: 258.05282342 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 641-38-3
• 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one
• 3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one
• CCRIS 6734
• CHEBI:64983
• 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one
• AOH
• BRN 0244839
• UNII-KN9L4260JW
• KN9L4260JW
• NSC638263
• 6H-DIBENZO(b,d)PYRAN-6-ONE, 1-METHYL-3,7,9-TRIHYDROXY-
• 3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid, gamma lactone
• 5-18-04-00516 (Beilstein Handbook Reference)
• 6H-Dibenzo[b,d]pyran-6-one, 3,7,9-trihydroxy-1-methyl-
• 3,7,9-Trihydroxy-1-methyl-6H-dibenzo(b,d)pyran-6-one
• Alternariol from Alternaria sp.
• CHEMBL519982
• MEGxm0_000137
• SCHEMBL1096830
• Alternariol, analytical standard
• ACon0_000598
• ACon1_001301
• DTXSID80214305
• CEBXXEKPIIDJHL-UHFFFAOYSA-N
• HY-N6714
• BDBM50479267
• MFCD00133068
• AKOS015916292
• CS-W020863
• NSC-638263
• Alternariol from Alternaria sp., ~96%
• NCGC00180653-01
• LS-61189
• NCI60_012751
• FT-0661536
• 3,4',5-Trihydroxy-6'-methyldibenzo-a-pyrone
• F85636
• 3,4',5-trihydroxy-6'-methyldibenzo-alpha-pyrone
• 3,7,9-trihydroxy-1-methyl-benzo[c]chromen-6-one
• A867945
• Q410677
• BRD-K62196712-001-01-3
• 1-Methyl-3,7,9-trihydroxy-6H-Dibenzo(b,D)pyran-6-one
• 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one #
• Alternariol 3,4',5-Trihydroxy-6'-methyl-dibenzo[a]pyrone
• 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,D]pyran-6-one, 9CI
• BrOP ?Bromotris(dimethylamino)phosphonium Hexafluorophosphate
• 3,4,4'-trihydroxy-6'-methyl-2-biphenylcarboxylic acid gamma-lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9472	94.72%
Caco-2	+	0.6545	65.45%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5694	56.94%
OATP2B1 inhibitior	-	0.6976	69.76%
OATP1B1 inhibitior	+	0.9328	93.28%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8650	86.50%
P-glycoprotein inhibitior	-	0.9077	90.77%
P-glycoprotein substrate	-	0.8879	88.79%
CYP3A4 substrate	-	0.5431	54.31%
CYP2C9 substrate	+	0.6360	63.60%
CYP2D6 substrate	-	0.8834	88.34%
CYP3A4 inhibition	+	0.7556	75.56%
CYP2C9 inhibition	-	0.7467	74.67%
CYP2C19 inhibition	-	0.8813	88.13%
CYP2D6 inhibition	-	0.9402	94.02%
CYP1A2 inhibition	+	0.7511	75.11%
CYP2C8 inhibition	-	0.8002	80.02%
CYP inhibitory promiscuity	-	0.6794	67.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5806	58.06%
Eye corrosion	-	0.9740	97.40%
Eye irritation	+	0.9861	98.61%
Skin irritation	+	0.5321	53.21%
Skin corrosion	-	0.9518	95.18%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7495	74.95%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.9170	91.70%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6136	61.36%
Acute Oral Toxicity (c)	III	0.8271	82.71%
Estrogen receptor binding	+	0.8058	80.58%
Androgen receptor binding	+	0.6683	66.83%
Thyroid receptor binding	-	0.5626	56.26%
Glucocorticoid receptor binding	+	0.8921	89.21%
Aromatase binding	+	0.5426	54.26%
PPAR gamma	+	0.6636	66.36%
Honey bee toxicity	-	0.9042	90.42%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8710	87.10%

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	97.88%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.16%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	93.47%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	93.41%	93.65%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.07%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	92.11%	91.49%
CHEMBL2581	P07339	Cathepsin D	90.75%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.72%	96.12%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.96%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.71%	99.23%
CHEMBL3194	P02766	Transthyretin	82.25%	90.71%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.41%	94.42%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.68%	99.15%

Plants that contains it

• Adenocarpus foliolosus
• Citrus × aurantium
• Equisetum hyemale
• Sonneratia alba
• Sorghum bicolor

Cross-Links

• PubChem: 5359485
• NPASS: NPC32470
• LOTUS: LTS0210335
• wikiData: Q410677