Fisetinidol

Details

• Internal ID: 3b56d379-38d3-4b4f-b571-556b48abc9c4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavan-3-ols
• IUPAC Name: (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,7-diol
• SMILES (Canonical): C1C(C(OC2=C1C=CC(=C2)O)C3=CC(=C(C=C3)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C=CC(=C2)O)C3=CC(=C(C=C3)O)O)O
• InChI: InChI=1S/C15H14O5/c16-10-3-1-8-5-13(19)15(20-14(8)7-10)9-2-4-11(17)12(18)6-9/h1-4,6-7,13,15-19H,5H2/t13-,15+/m0/s1
• InChI Key: VFZYLYJWCROVLO-DZGCQCFKSA-N
• Popularity: 46 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27 g/mol
• Exact Mass: 274.08412354 g/mol
• Topological Polar Surface Area (TPSA): 90.20 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.84
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 490-49-3
• CHEBI:5066
• 3,7,3',4'-Tetrahydroxyflavan
• (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,7-diol
• Spectrum_001710
• SpecPlus_000717
• Spectrum2_000423
• Spectrum3_000237
• Spectrum4_001574
• Spectrum5_000228
• C09735
• BSPBio_001913
• KBioGR_002128
• KBioSS_002190
• SPECTRUM210014
• DivK1c_006813
• SPBio_000406
• SCHEMBL1851553
• CHEMBL3039234
• KBio1_001757
• KBio2_002190
• KBio2_004758
• KBio2_007326
• KBio3_001413
• DTXSID401028831
• CCG-38683
• LMPK12020013
• NCGC00178911-01
• Q5454456
• (2R,3S)-2-(3,4-Dihydroxyphenyl)-3,7-chromanediol
• (2R,3S)-2-(3,4-dihydroxyphenyl)chroman-3,7-diol
• BRD-K89853519-001-01-3
• 2H-1-Benzopyran-3,7-diol,2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2R,3S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9525	95.25%
Caco-2	-	0.8429	84.29%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6412	64.12%
OATP2B1 inhibitior	-	0.5829	58.29%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9905	99.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8770	87.70%
P-glycoprotein inhibitior	-	0.9252	92.52%
P-glycoprotein substrate	-	0.8994	89.94%
CYP3A4 substrate	-	0.5428	54.28%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	+	0.5322	53.22%
CYP3A4 inhibition	-	0.9101	91.01%
CYP2C9 inhibition	-	0.5182	51.82%
CYP2C19 inhibition	-	0.7972	79.72%
CYP2D6 inhibition	-	0.8775	87.75%
CYP1A2 inhibition	-	0.6470	64.70%
CYP2C8 inhibition	-	0.6685	66.85%
CYP inhibitory promiscuity	-	0.7482	74.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5062	50.62%
Eye corrosion	-	0.9898	98.98%
Eye irritation	+	0.9340	93.40%
Skin irritation	-	0.5331	53.31%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6191	61.91%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.7686	76.86%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7928	79.28%
Acute Oral Toxicity (c)	II	0.3395	33.95%
Estrogen receptor binding	-	0.6025	60.25%
Androgen receptor binding	+	0.5512	55.12%
Thyroid receptor binding	+	0.7617	76.17%
Glucocorticoid receptor binding	+	0.6997	69.97%
Aromatase binding	+	0.6169	61.69%
PPAR gamma	+	0.7032	70.32%
Honey bee toxicity	-	0.8524	85.24%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7632	76.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4040	P28482	MAP kinase ERK2	158.5 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.26%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.81%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.41%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.37%	97.09%
CHEMBL217	P14416	Dopamine D2 receptor	89.20%	95.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.10%	99.15%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	85.19%	91.79%
CHEMBL236	P41143	Delta opioid receptor	85.17%	99.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.08%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	84.78%	94.73%
CHEMBL3438	Q05513	Protein kinase C zeta	82.64%	88.48%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.86%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.82%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.02%	95.89%

Plants that contains it

• Acacia dealbata
• Acacia mearnsii
• Burkea africana
• Castela tortuosa
• Colophospermum mopane
• Virola elongata

Cross-Links

• PubChem: 442397
• LOTUS: LTS0143893
• wikiData: Q5454456