Ochnaflavone

Details

• Internal ID: d7d77665-42c2-435d-ae5c-9a3661b8190b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 2-[4-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]phenyl]-5,7-dihydroxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)OC4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)OC4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O
• InChI: InChI=1S/C30H18O10/c31-16-8-20(34)29-22(36)12-24(39-27(29)10-16)14-1-4-18(5-2-14)38-26-7-15(3-6-19(26)33)25-13-23(37)30-21(35)9-17(32)11-28(30)40-25/h1-13,31-35H
• InChI Key: NNPGECDACGBKDH-UHFFFAOYSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₁₈O₁₀
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.08999677 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.55
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 50276-96-5
• 2-[4-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]phenyl]-5,7-dihydroxychromen-4-one
• 5B97Q9UZ5T
• 4H-1-Benzopyran-4-one, 2-(4-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenoxy)phenyl)-5,7-dihydroxy-
• 4H-1-Benzopyran-4-one, 2-[4-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenoxy]phenyl]-5,7-dihydroxy-
• Ochnaflavone7-O-beta-D-gluco-pyranoside
• D0Y0OA
• UNII-5B97Q9UZ5T
• SCHEMBL13829452
• DTXSID70198281
• CHEBI:194126
• AKOS016010710
• Q17099497
• 2-(4-(5-(5,7-BIS(OXIDANYL)-4-OXIDANYLIDENE-CHROMEN-2-YL)-2-OXIDANYL-PHENOXY)PHENYL)-5,7-BIS(OXIDANYL)CHROMEN-4-ONE
• 2-{4-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy]phenyl}-5,7-dihydroxy-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8926	89.26%
Caco-2	-	0.8573	85.73%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6583	65.83%
OATP2B1 inhibitior	+	0.5753	57.53%
OATP1B1 inhibitior	+	0.9296	92.96%
OATP1B3 inhibitior	+	0.8553	85.53%
MATE1 inhibitior	+	0.6800	68.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4865	48.65%
P-glycoprotein inhibitior	+	0.7477	74.77%
P-glycoprotein substrate	-	0.9274	92.74%
CYP3A4 substrate	+	0.5565	55.65%
CYP2C9 substrate	-	0.6218	62.18%
CYP2D6 substrate	-	0.8508	85.08%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	+	0.8318	83.18%
CYP2C19 inhibition	+	0.6307	63.07%
CYP2D6 inhibition	-	0.9004	90.04%
CYP1A2 inhibition	+	0.6264	62.64%
CYP2C8 inhibition	+	0.8639	86.39%
CYP inhibitory promiscuity	+	0.5994	59.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6849	68.49%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.7265	72.65%
Skin irritation	-	0.5751	57.51%
Skin corrosion	-	0.9492	94.92%
Ames mutagenesis	-	0.5128	51.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.5312	53.12%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8792	87.92%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5452	54.52%
Acute Oral Toxicity (c)	II	0.4709	47.09%
Estrogen receptor binding	+	0.8581	85.81%
Androgen receptor binding	+	0.9240	92.40%
Thyroid receptor binding	+	0.6319	63.19%
Glucocorticoid receptor binding	+	0.8412	84.12%
Aromatase binding	+	0.6963	69.63%
PPAR gamma	+	0.8091	80.91%
Honey bee toxicity	-	0.7342	73.42%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5199	51.99%
Fish aquatic toxicity	+	0.9181	91.81%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3474	P14555	Phospholipase A2 group IIA	3500 nM	IC50	PMID: 16504502

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.45%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	98.22%	99.15%
CHEMBL3194	P02766	Transthyretin	98.03%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.54%	94.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.32%	96.12%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	93.12%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.10%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.54%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.40%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.01%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.66%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.95%	83.57%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.10%	93.65%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.33%	99.17%
CHEMBL4208	P20618	Proteasome component C5	85.21%	90.00%
CHEMBL2581	P07339	Cathepsin D	84.91%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.84%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.69%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	81.41%	94.73%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	81.40%	89.23%
CHEMBL242	Q92731	Estrogen receptor beta	80.36%	98.35%

Plants that contains it

• Acacia aulacocarpa
• Anemonastrum flaccidum
• Ardisia neriifolia
• Aspidosperma subincanum
• Cryptocarya aschersoniana
• Eupatorium argentinum
• Garcinia madruno
• Guatteria ucayalina
• Juniperus brevifolia
• Lonicera japonica
• Ochna gamblei
• Ochna obtusata
• Peritassa compta
• Psiadia dentata

Cross-Links

• PubChem: 5492110
• NPASS: NPC112954
• ChEMBL: CHEMBL187504
• LOTUS: LTS0243620
• wikiData: Q17099497