6-Methoxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one

Details

• Internal ID: 4068096b-c205-42a6-87fb-f538a1f29ef4
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 6-methoxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C=CC(=O)O2)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C=CC(=O)O2)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3
• InChI Key: SGTCGCCQZOUMJJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₉
• Molecular Weight: 354.31 g/mol
• Exact Mass: 354.09508215 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.02
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• 6-methoxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• 2H-1-Benzopyran-2-one, 7-(.beta.-D-glucopyranosyloxy)-6-methoxy-
• SCHEMBL14296928
• CHEBI:182227
• 6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• 7-(beta-D-Glucopyranosyloxy)-6-methoxy-2H-1-benzopyran-2-one
• NSC404560

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5647	56.47%
Caco-2	-	0.8435	84.35%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5367	53.67%
OATP2B1 inhibitior	-	0.8470	84.70%
OATP1B1 inhibitior	+	0.8846	88.46%
OATP1B3 inhibitior	+	0.9769	97.69%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7156	71.56%
P-glycoprotein inhibitior	-	0.8887	88.87%
P-glycoprotein substrate	-	0.8168	81.68%
CYP3A4 substrate	-	0.5201	52.01%
CYP2C9 substrate	-	0.8306	83.06%
CYP2D6 substrate	-	0.8491	84.91%
CYP3A4 inhibition	-	0.9107	91.07%
CYP2C9 inhibition	-	0.9346	93.46%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9306	93.06%
CYP1A2 inhibition	-	0.8772	87.72%
CYP2C8 inhibition	-	0.7234	72.34%
CYP inhibitory promiscuity	-	0.8094	80.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6881	68.81%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9405	94.05%
Skin irritation	-	0.8111	81.11%
Skin corrosion	-	0.9624	96.24%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.6133	61.33%
Hepatotoxicity	-	0.7476	74.76%
skin sensitisation	-	0.9164	91.64%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7485	74.85%
Acute Oral Toxicity (c)	III	0.7058	70.58%
Estrogen receptor binding	+	0.5321	53.21%
Androgen receptor binding	-	0.5304	53.04%
Thyroid receptor binding	-	0.5953	59.53%
Glucocorticoid receptor binding	+	0.6966	69.66%
Aromatase binding	+	0.5820	58.20%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8771	87.71%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6949	69.49%
Fish aquatic toxicity	+	0.6492	64.92%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3242	O43570	Carbonic anhydrase XII	780 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	98.58%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.17%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.88%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.87%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.06%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.73%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.65%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.06%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.71%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.67%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	84.10%	94.73%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.81%	94.03%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.62%	86.92%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.03%	89.62%

Plants that contains it

• Acer saccharum
• Aesculus pavia
• Althaea officinalis
• Artemisia capillaris
• Artemisia chamaemelifolia
• Artemisia ordosica
• Artemisia suksdorfii
• Astragalus falcatus
• Astragalus onobrychis
• Catunaregam obovata
• Cephalanthus occidentalis
• Diplolophium buchananii
• Echinacea purpurea
• Eucalyptus viminalis
• Eurycoma longifolia
• Evolvulus alsinoides
• Falconeria insignis
• Haplophyllum acutifolium
• Helichrysum arenarium
• Himalrandia tetrasperma
• Inulanthera nuda
• Ipomoea nil
• Macaranga tanarius
• Mandragora officinarum
• Mentzelia albescens
• Morus alba
• Murraya paniculata
• Neonauclea sessilifolia
• Olea europaea subsp. cuspidata
• Physochlaina physaloides
• Quassia undulata
• Ripariosida hermaphrodita
• Salsola laricifolia
• Saussurea cordifolia
• Saussurea hieracioides
• Skimmia japonica
• Viburnum odoratissimum var. awabuki
• Weigela subsessilis

Cross-Links

• PubChem: 346340
• LOTUS: LTS0042457
• wikiData: Q104667950