Balanophonin

Details

• Internal ID: 296c77df-4080-4446-9bc2-da7fefa3bea0
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (E)-3-[(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)O)OC)C=CC=O
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@H]([C@@H]2CO)C3=CC(=C(C=C3)O)OC)/C=C/C=O
• InChI: InChI=1S/C20H20O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h3-10,15,19,22-23H,11H2,1-2H3/b4-3+/t15-,19+/m1/s1
• InChI Key: GWCSSLSMGCFIFR-GWKPYITFSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.12598835 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.83
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 80286-36-8
• (?)-Balanophonin
• (-)-dehydrodiconiferyl aldehyde
• CHEMBL1956166
• (-)-DCA-L
• DTXSID001318030
• HY-N10782
• CS-0636029
• (2E)-3-[(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydrobenzofuran-5-yl] acrylaldehyde
• 2beta-(3-Methoxy-4-hydroxyphenyl)-3alpha-hydroxymethyl-7-methoxy-2,3-dihydrobenzofuran 5-acrylaldehyde

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	+	0.5190	51.90%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7716	77.16%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8583	85.83%
OATP1B3 inhibitior	+	0.8668	86.68%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7674	76.74%
P-glycoprotein inhibitior	+	0.6699	66.99%
P-glycoprotein substrate	-	0.8335	83.35%
CYP3A4 substrate	+	0.5620	56.20%
CYP2C9 substrate	+	0.6044	60.44%
CYP2D6 substrate	-	0.7908	79.08%
CYP3A4 inhibition	+	0.5855	58.55%
CYP2C9 inhibition	+	0.8941	89.41%
CYP2C19 inhibition	+	0.8422	84.22%
CYP2D6 inhibition	-	0.7789	77.89%
CYP1A2 inhibition	+	0.6462	64.62%
CYP2C8 inhibition	+	0.6587	65.87%
CYP inhibitory promiscuity	+	0.9524	95.24%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5429	54.29%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.7820	78.20%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4152	41.52%
Micronuclear	+	0.7659	76.59%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.7502	75.02%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.4680	46.80%
Acute Oral Toxicity (c)	III	0.5707	57.07%
Estrogen receptor binding	+	0.8186	81.86%
Androgen receptor binding	+	0.6952	69.52%
Thyroid receptor binding	+	0.6229	62.29%
Glucocorticoid receptor binding	+	0.6525	65.25%
Aromatase binding	+	0.5745	57.45%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8703	87.03%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9620	96.20%

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	98.30%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.18%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.14%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.87%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.33%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.93%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.78%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	90.23%	94.73%
CHEMBL3194	P02766	Transthyretin	86.48%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.19%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.11%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.76%	97.09%

Plants that contains it

• Aeginetia indica
• Amentotaxus yunnanensis
• Artemisia annua
• Buddleja davidii
• Carya cathayensis
• Handroanthus impetiginosus
• Lonicera morrowii
• Mallotus nudiflorus
• Morinda citrifolia
• Tarenna attenuata
• Zanthoxylum integrifoliolum

Cross-Links

• PubChem: 21582569
• NPASS: NPC284881
• ChEMBL: CHEMBL1956166
• LOTUS: LTS0130349
• wikiData: Q76512002