Daphnodorin A

Details

• Internal ID: 29818950-3207-4947-8e36-cff49c1de89d
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: [(2S)-5-hydroxy-2,8-bis(4-hydroxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl]-(2,4,6-trihydroxyphenyl)methanone
• SMILES (Canonical): C1CC2=C(C3=C(C=C2O)OC(=C3C(=O)C4=C(C=C(C=C4O)O)O)C5=CC=C(C=C5)O)OC1C6=CC=C(C=C6)O
• SMILES (Isomeric): C1CC2=C(C3=C(C=C2O)OC(=C3C(=O)C4=C(C=C(C=C4O)O)O)C5=CC=C(C=C5)O)O[C@@H]1C6=CC=C(C=C6)O
• InChI: InChI=1S/C30H22O9/c31-16-5-1-14(2-6-16)23-10-9-19-20(34)13-24-26(30(19)38-23)27(29(39-24)15-3-7-17(32)8-4-15)28(37)25-21(35)11-18(33)12-22(25)36/h1-8,11-13,23,31-36H,9-10H2/t23-/m0/s1
• InChI Key: SFIBBWQCUADULX-QHCPKHFHSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₂O₉
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.12638228 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.63
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 95733-03-2
• [(2S)-5-hydroxy-2,8-bis(4-hydroxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl]-(2,4,6-trihydroxyphenyl)methanone
• (-)-(3,4-Dihydro-5-hydroxy-2,8-bis(4-hydroxyphenyl)-2H-furo(2,3-h)-1-benzopyran-9-yl)(2,4,6-trihydroxyphenyl)methanone
• C30H22O9
• CHEMBL2273051
• DTXSID10241942
• [3,4-Dihydro-5-hydroxy-2,8-bis(4-hydroxyphenyl)-2H-furo[2,3-h]-1-benzopyran-9-yl](2,4,6-trihydroxyphenyl)methanone, (-)-
• Methanone, (3,4-dihydro-5-hydroxy-2,8-bis(4-hydroxyphenyl)-2H-furo(2,3-h)-1-benzopyran-9-yl)(2,4,6-trihydroxyphenyl)-, (-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9449	94.49%
Caco-2	-	0.8428	84.28%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8817	88.17%
OATP2B1 inhibitior	-	0.5626	56.26%
OATP1B1 inhibitior	+	0.8719	87.19%
OATP1B3 inhibitior	+	0.8620	86.20%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8108	81.08%
BSEP inhibitior	+	0.7316	73.16%
P-glycoprotein inhibitior	+	0.7829	78.29%
P-glycoprotein substrate	-	0.6420	64.20%
CYP3A4 substrate	+	0.6189	61.89%
CYP2C9 substrate	-	0.6131	61.31%
CYP2D6 substrate	-	0.7754	77.54%
CYP3A4 inhibition	+	0.5988	59.88%
CYP2C9 inhibition	+	0.8108	81.08%
CYP2C19 inhibition	+	0.7535	75.35%
CYP2D6 inhibition	-	0.7669	76.69%
CYP1A2 inhibition	+	0.7826	78.26%
CYP2C8 inhibition	+	0.9046	90.46%
CYP inhibitory promiscuity	+	0.5213	52.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4914	49.14%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.7112	71.12%
Skin irritation	-	0.6552	65.52%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8478	84.78%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8240	82.40%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8415	84.15%
Acute Oral Toxicity (c)	I	0.3902	39.02%
Estrogen receptor binding	+	0.8190	81.90%
Androgen receptor binding	+	0.8880	88.80%
Thyroid receptor binding	+	0.5800	58.00%
Glucocorticoid receptor binding	+	0.7014	70.14%
Aromatase binding	+	0.5224	52.24%
PPAR gamma	+	0.6953	69.53%
Honey bee toxicity	-	0.8339	83.39%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.8004	80.04%

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	98.52%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.24%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.57%	97.09%
CHEMBL3194	P02766	Transthyretin	92.47%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	92.27%	95.78%
CHEMBL242	Q92731	Estrogen receptor beta	90.07%	98.35%
CHEMBL217	P14416	Dopamine D2 receptor	89.68%	95.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.15%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.95%	94.45%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.95%	96.12%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.08%	95.64%
CHEMBL2581	P07339	Cathepsin D	84.76%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.73%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.72%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	83.68%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.58%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.73%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.74%	99.15%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.20%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.04%	99.17%

Plants that contains it

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

Cross-Links

• PubChem: 72426
• NPASS: NPC38591
• LOTUS: LTS0217816
• wikiData: Q83125491