Maritimein

Details

• Internal ID: b34eef56-18db-40c2-851f-bd5eaa5ae3af
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Aurone O-glycosides
• IUPAC Name: (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-benzofuran-3-one
• SMILES (Canonical): C1=CC(=C(C=C1C=C2C(=O)C3=C(O2)C(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C\2/C(=O)C3=C(O2)C(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-14-16(26)18(28)19(29)21(32-14)31-12-4-2-9-15(25)13(30-20(9)17(12)27)6-8-1-3-10(23)11(24)5-8/h1-6,14,16,18-19,21-24,26-29H,7H2/b13-6-/t14-,16-,18+,19-,21-/m1/s1
• InChI Key: SYRURBPRFQUYQS-RHEJLWEFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.40
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• 490-54-0
• UNII-4PTU0WDQ7M
• 4PTU0WDQ7M
• EINECS 207-712-2
• (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-benzofuran-3-one
• (Z)-2-((3,4-Dihydroxyphenyl)methylene)-6-(beta-D-glucopyranosyloxy)-7-hydroxybenzofuran-3(2H)-one
• SCHEMBL1706306
• CHEMBL2165570
• DTXSID901029272
• HY-N8955
• MFCD00017413
• AKOS040762024
• CS-0149432
• A827647
• Q6765897
• (Z)-2-((3,4-DIHYDROXYPHENYL)METHYLENE)-6-(.BETA.-D-GLUCOPYRANOSYLOXY)-7-HYDROXYBENZOFURAN-3(2H)-ONE
• 3(2H)-BENZOFURANONE, 2-((3,4-DIHYDROXYPHENYL)METHYLENE)-6-(.BETA.-D-GLUCOPYRANOSYLOXY)-7-HYDROXY-, (2Z)-
• 3(2H)-BENZOFURANONE, 2-((3,4-DIHYDROXYPHENYL)METHYLENE)-6-(.BETA.-D-GLUCOPYRANOSYLOXY)-7-HYDROXY-, (Z)-
• 3(2H)-BENZOFURANONE, 2-(3,4-DIHYDROXYBENZYLIDENE)-6-(.BETA.-D-GLUCOPYRANOSYLOXY)-7-HYDROXY-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7573	75.73%
Caco-2	-	0.9527	95.27%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6583	65.83%
OATP2B1 inhibitior	-	0.5434	54.34%
OATP1B1 inhibitior	+	0.8907	89.07%
OATP1B3 inhibitior	+	0.9614	96.14%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5590	55.90%
P-glycoprotein inhibitior	-	0.7506	75.06%
P-glycoprotein substrate	-	0.8636	86.36%
CYP3A4 substrate	+	0.5853	58.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8434	84.34%
CYP3A4 inhibition	-	0.8343	83.43%
CYP2C9 inhibition	-	0.8566	85.66%
CYP2C19 inhibition	-	0.7065	70.65%
CYP2D6 inhibition	-	0.8217	82.17%
CYP1A2 inhibition	-	0.7979	79.79%
CYP2C8 inhibition	+	0.6275	62.75%
CYP inhibitory promiscuity	+	0.5372	53.72%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6352	63.52%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.7861	78.61%
Skin irritation	-	0.7825	78.25%
Skin corrosion	-	0.9563	95.63%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5928	59.28%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.7870	78.70%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7925	79.25%
Acute Oral Toxicity (c)	III	0.4589	45.89%
Estrogen receptor binding	+	0.6875	68.75%
Androgen receptor binding	+	0.6590	65.90%
Thyroid receptor binding	+	0.5688	56.88%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5236	52.36%
PPAR gamma	+	0.7438	74.38%
Honey bee toxicity	-	0.6674	66.74%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9415	94.15%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.97%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.19%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.97%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.01%	95.56%
CHEMBL3194	P02766	Transthyretin	92.37%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.30%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.25%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	87.13%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.75%	80.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.35%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.85%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.49%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.84%	95.89%
CHEMBL4208	P20618	Proteasome component C5	82.35%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.54%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.15%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.38%	100.00%

Plants that contains it

• Bidens bipinnata
• Bidens pilosa
• Coreopsis maritima
• Coreopsis tinctoria
• Cynara humilis
• Viguiera dentata

Cross-Links

• PubChem: 6450184
• LOTUS: LTS0140411
• wikiData: Q6765897