Fustin

Details

• Internal ID: 68db6619-0512-40b1-b1e3-87d3e427b26f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1[C@@H]2[C@H](C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
• InChI: InChI=1S/C15H12O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,14-18,20H/t14-,15+/m0/s1
• InChI Key: FNUPUYFWZXZMIE-LSDHHAIUSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25 g/mol
• Exact Mass: 288.06338810 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.48
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 20725-03-5
• 2,3-Dihydrofisetin
• Dihydrofisetin
• Fustin, (+)-
• (+)-Fustin
• 3,7,3',4'-Tetrahydroxyflavanone
• 4382-36-9
• Fustin (2R,3R)-form [MI]
• UNII-4994C1X19A
• (+/-)-Fustin
• EINECS 243-989-6
• NSC 59264
• 4994C1X19A
• UNII-C308QR79UE
• C308QR79UE
• CHEMBL470267
• Flavanone, 3,3',4',7-tetrahydroxy-, (+)-
• Tetrahydroxyflavanone
• (2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-2,3-dihydrochromen-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-, (2R,3R)-
• NSC-59264
• trans-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-4-benzopyrone
• (2R,3R)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-, (2R,3R)-rel-
• AC1NSVLG
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-, trans-
• CHEBI:5202
• 3,3',4',7-tetrahydroxyflavanone
• FUSTIN [MI]
• 2,3-TRANS-FUSTIN
• SureCN13640269
• Ambap20725-03-5
• SCHEMBL13640269
• DTXSID70871986
• FUSTIN, (+/-)-
• (2R,3R)-rel-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-4H-1-benzopyran-4-one
• (2R,3S)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
• DTXSID401136309
• 3,7,3',4'-Tetrahydroxy-flavanon
• HY-N8376
• MFCD00075647
• AKOS032948206
• CS-0143760
• Flavanone, 3,3',4',7-tetrahydroxy-(VAN)
• (2alpha)-3beta,3',4',7-Tetrahydroxyflavanone
• C01378
• Flavanone, 3,3',4',7-tetrahydroxy- (VAN)
• Q5510352
• TRANS-(+/-)-3,3',4',7-TETRAHYDROXYFLAVANONE
• (2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxychroman-4-one
• (2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-chroman-4-one
• 4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-,(2R,3R)-rel-
• 4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-2,3-DIHYDRO-3,7-DIHYDROXY-, (2R-TRANS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9569	95.69%
Caco-2	-	0.8745	87.45%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7742	77.42%
OATP2B1 inhibitior	-	0.7007	70.07%
OATP1B1 inhibitior	+	0.9136	91.36%
OATP1B3 inhibitior	+	0.9902	99.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8259	82.59%
P-glycoprotein inhibitior	-	0.8850	88.50%
P-glycoprotein substrate	-	0.9450	94.50%
CYP3A4 substrate	-	0.5129	51.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7351	73.51%
CYP3A4 inhibition	-	0.7054	70.54%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	-	0.6965	69.65%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9249	92.49%
CYP2C8 inhibition	-	0.6597	65.97%
CYP inhibitory promiscuity	-	0.5409	54.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5926	59.26%
Eye corrosion	-	0.9890	98.90%
Eye irritation	+	0.9788	97.88%
Skin irritation	+	0.6100	61.00%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8415	84.15%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8006	80.06%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.5654	56.54%
Acute Oral Toxicity (c)	II	0.7187	71.87%
Estrogen receptor binding	+	0.5816	58.16%
Androgen receptor binding	+	0.5995	59.95%
Thyroid receptor binding	+	0.7274	72.74%
Glucocorticoid receptor binding	+	0.7556	75.56%
Aromatase binding	+	0.6631	66.31%
PPAR gamma	+	0.6391	63.91%
Honey bee toxicity	-	0.8562	85.62%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9311	93.11%

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	99.16%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.61%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.29%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.96%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.62%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.76%	99.15%
CHEMBL3194	P02766	Transthyretin	86.30%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.46%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.25%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.35%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.01%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.99%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.23%	90.71%

Plants that contains it

• Acacia baileyana
• Acacia carneorum
• Acacia crombiei
• Acacia fasciculifera
• Acacia mollifolia
• Acacia peuce
• Acacia saxatilis
• Acacia terminalis
• Acicarpha tribuloides
• Aconitum palmatum
• Aconitum rotundifolium
• Aesculus turbinata
• Alnus alnobetula
• Aniba rosaeodora
• Argyreia nervosa
• Ariocarpus fissuratus
• Artocarpus styracifolius
• Baptisia lecontei
• Bidens tripartita
• Brucea javanica
• Carpesium faberi
• Cheirolophus arbutifolius
• Codonopsis cordifolioidea
• Corydalis sewerzowi
• Corymbia citriodora
• Cotinus coggygria
• Culcitium albifolium
• Dahlstedtia pentaphylla
• Dorstenia mannii
• Flemingia prostrata
• Forsythia giraldiana
• Genista sessilifolia
• Gleditsia japonica
• Gomphostemma parviflorum
• Hasteola robusta
• Hippobroma longiflora
• Hirtellina fruticosa
• Hypericum japonicum
• Krameria erecta
• Lawsonia inermis
• Onoseris alata
• Piper acutifolium
• Prosopidastrum globosum
• Psilotum nudum
• Robinia pseudoacacia
• Swertia diluta
• Toxicodendron vernicifluum
• Trapa natans var. bicornis
• Vellozia streptophylla
• Xyris indica

Cross-Links

• PubChem: 5317435
• NPASS: NPC27532
• ChEMBL: CHEMBL470267
• LOTUS: LTS0228197
• wikiData: Q5510352