2'-Hydroxybiochanin A

Details

• Internal ID: c5696585-1090-475c-9965-1c9c3319ef65
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 4-O-methylated isoflavonoids > 4-O-methylisoflavones
• IUPAC Name: 5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC(=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O)O
• SMILES (Isomeric): COC1=CC(=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O)O
• InChI: InChI=1S/C16H12O6/c1-21-9-2-3-10(12(18)6-9)11-7-22-14-5-8(17)4-13(19)15(14)16(11)20/h2-7,17-19H,1H3
• InChI Key: OZEVXMDBOINMTC-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26 g/mol
• Exact Mass: 300.06338810 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• Dehydroferreirin
• 32884-35-8
• 2''-HYDROXYBIOCHANIN A
• CHEBI:31064
• CHEMBL403228
• DTXSID901314873
• LMPK12050328
• 2',5,7-trihydroxy-4'-methoxyisoflavone
• 5,7,2'-Trihydroxy-4'-methoxyisoflavone
• Q27114114
• 5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9694	96.94%
Caco-2	+	0.7770	77.70%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7877	78.77%
OATP2B1 inhibitior	-	0.5579	55.79%
OATP1B1 inhibitior	+	0.9150	91.50%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7618	76.18%
P-glycoprotein inhibitior	-	0.8214	82.14%
P-glycoprotein substrate	-	0.8987	89.87%
CYP3A4 substrate	+	0.5526	55.26%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.7746	77.46%
CYP2C9 inhibition	+	0.8287	82.87%
CYP2C19 inhibition	+	0.9470	94.70%
CYP2D6 inhibition	-	0.6939	69.39%
CYP1A2 inhibition	+	0.9540	95.40%
CYP2C8 inhibition	+	0.5554	55.54%
CYP inhibitory promiscuity	+	0.8845	88.45%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6169	61.69%
Eye corrosion	-	0.9796	97.96%
Eye irritation	+	0.8722	87.22%
Skin irritation	-	0.6033	60.33%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8338	83.38%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9484	94.84%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6484	64.84%
Acute Oral Toxicity (c)	III	0.7005	70.05%
Estrogen receptor binding	+	0.9350	93.50%
Androgen receptor binding	+	0.8911	89.11%
Thyroid receptor binding	+	0.7729	77.29%
Glucocorticoid receptor binding	+	0.8063	80.63%
Aromatase binding	+	0.8450	84.50%
PPAR gamma	+	0.5458	54.58%
Honey bee toxicity	-	0.9174	91.74%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8717	87.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.19%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.62%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.62%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	94.90%	96.12%
CHEMBL4208	P20618	Proteasome component C5	94.40%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.74%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.66%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.27%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.25%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.08%	89.00%
CHEMBL2535	P11166	Glucose transporter	85.09%	98.75%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.00%	93.65%
CHEMBL1951	P21397	Monoamine oxidase A	84.17%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.47%	99.23%
CHEMBL1907	P15144	Aminopeptidase N	81.32%	93.31%

Plants that contains it

• Abies alba
• Abies pinsapo subsp. marocana
• Ampelocera edentula
• Angelica acutiloba
• Arnica mollis
• Aspilia foliosa
• Astragalus laxmannii
• Astragalus laxmannii subsp. laxmannii
• Barringtonia acutangula
• Brassica carinata
• Bryonia alba
• Carpha glomerata
• Corydalis densiflora
• Craibiodendron yunnanense
• Croton gratissimus
• Cyanostegia angustifolia
• Dactylorhiza viridis
• Dalbergia congestiflora
• Dalbergia parviflora
• Desmodium canadense
• Diplopterygium glaucum
• Embelia ribes
• Eucalyptus resinifera
• Euchresta formosana
• Euphrasia nana
• Eurycoma harmandiana
• Ficus nymphaeifolia
• Ixeris japonica
• Khaya grandifoliola
• Lysimachia fordiana
• Mabea fistulifera
• Napoleonaea vogelii
• Orthosiphon aristatus
• Oxytropis falcata
• Pterolobium hexapetalum
• Ranunculus asiaticus
• Remirea maritima
• Schleichera oleosa
• Schultesia guianensis
• Sinapis alba
• Solanum lanceolatum
• Triclisia subcordata
• Viburnum erubescens
• Virola caducifolia
• Wikstroemia indica
• Xanthorhiza simplicissima

Cross-Links

• PubChem: 5282075
• NPASS: NPC279668
• LOTUS: LTS0165599
• wikiData: Q27114114