Daphnodorin B

Details

• Internal ID: 3a8a0b72-28e3-4be1-a304-728a643612fe
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: [(2R,3S)-3,5-dihydroxy-2,8-bis(4-hydroxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl]-(2,4,6-trihydroxyphenyl)methanone
• SMILES (Canonical): C1C(C(OC2=C1C(=CC3=C2C(=C(O3)C4=CC=C(C=C4)O)C(=O)C5=C(C=C(C=C5O)O)O)O)C6=CC=C(C=C6)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC3=C2C(=C(O3)C4=CC=C(C=C4)O)C(=O)C5=C(C=C(C=C5O)O)O)O)C6=CC=C(C=C6)O)O
• InChI: InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)28-22(37)11-18-19(34)12-23-25(30(18)40-28)26(29(39-23)14-3-7-16(32)8-4-14)27(38)24-20(35)9-17(33)10-21(24)36/h1-10,12,22,28,31-37H,11H2/t22-,28+/m0/s1
• InChI Key: JBNFGJOTOPTIDE-RBISFHTESA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₂O₁₀
• Molecular Weight: 542.50 g/mol
• Exact Mass: 542.12129689 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.60
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• 95733-02-1
• [(2R,3S)-3,5-dihydroxy-2,8-bis(4-hydroxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl]-(2,4,6-trihydroxyphenyl)methanone
• [(2r,3s)-3,5-dihydroxy-2,8-bis(4-hydroxyphenyl)-3,4-dihydro-2h-furo[2,3-h]chromen-9-yl](2,4,6-trihydroxyphenyl)methanone
• NSC698798
• SCHEMBL1229973
• CHEMBL2273052
• DTXSID50241941
• HY-N10961
• AKOS040734025
• NSC-698798
• CS-0637794
• [3,4-Dihydro-3,5-dihydro-2,8-bis(4-hydroxyphenyl)-2H-furo[2,3-h]benzopyran-9-yl](2,4,5-trihydroxyphenyl)methanone, trans-(-)
• Methanone, (3,4-dihydro-3,5-dihydroxy-2,8-bis(4-hydroxyphenyl)-2H-furo(2,3-h)-l-benzopyran-9-yl)(2,4,6-trihydroxyphenyl)-, trans-(-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9740	97.40%
Caco-2	-	0.8721	87.21%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6794	67.94%
OATP2B1 inhibitior	-	0.5548	55.48%
OATP1B1 inhibitior	+	0.7616	76.16%
OATP1B3 inhibitior	-	0.4619	46.19%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8028	80.28%
P-glycoprotein inhibitior	+	0.7734	77.34%
P-glycoprotein substrate	-	0.5516	55.16%
CYP3A4 substrate	+	0.6156	61.56%
CYP2C9 substrate	-	0.6091	60.91%
CYP2D6 substrate	-	0.7624	76.24%
CYP3A4 inhibition	-	0.5102	51.02%
CYP2C9 inhibition	-	0.5971	59.71%
CYP2C19 inhibition	-	0.6782	67.82%
CYP2D6 inhibition	-	0.8553	85.53%
CYP1A2 inhibition	-	0.6777	67.77%
CYP2C8 inhibition	+	0.8609	86.09%
CYP inhibitory promiscuity	-	0.6460	64.60%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5237	52.37%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.7810	78.10%
Skin irritation	-	0.6060	60.60%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8174	81.74%
Micronuclear	+	0.8959	89.59%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.7796	77.96%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7687	76.87%
Acute Oral Toxicity (c)	III	0.3558	35.58%
Estrogen receptor binding	+	0.7795	77.95%
Androgen receptor binding	+	0.8495	84.95%
Thyroid receptor binding	+	0.5833	58.33%
Glucocorticoid receptor binding	+	0.6743	67.43%
Aromatase binding	-	0.5478	54.78%
PPAR gamma	+	0.6755	67.55%
Honey bee toxicity	-	0.7730	77.30%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.7756	77.56%

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	99.00%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.04%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.55%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.91%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.26%	98.95%
CHEMBL3194	P02766	Transthyretin	89.15%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	87.93%	94.73%
CHEMBL217	P14416	Dopamine D2 receptor	87.15%	95.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.77%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.19%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.91%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.86%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.04%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.51%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.25%	95.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.71%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.55%	95.64%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.90%	89.23%
CHEMBL242	Q92731	Estrogen receptor beta	80.49%	98.35%

Plants that contains it

• Acer caudatifolium
• Aconitum heterophyllum
• Astragalus sinicus
• Baccharis macraei
• Cynoglossum lanceolatum
• Daphne feddei
• Daphne genkwa
• Daphne holosericea
• Daphne odora
• Klasea centauroides subsp. strangulata
• Leucoptera nodosa
• Lindera glauca
• Marshallia graminifolia
• Mikania goyazensis
• Oxytropis ochrocephala
• Rumohra adiantiformis
• Salacia cordata
• Solanum aculeatissimum
• Stellera chamaejasme
• Stenocephalum megapotamicum
• Syzygium sandwicense
• Wikstroemia indica
• Wikstroemia sikokiana

Cross-Links

• PubChem: 72427
• NPASS: NPC53252
• LOTUS: LTS0256408
• wikiData: Q83125490