daphnodorin D2

Details

• Internal ID: 7259b802-018f-4ce1-8fba-cc46ecde287f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 3-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1CC2=C(C(=C(C=C2O)O)C3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)OC1C6=CC=C(C=C6)O
• SMILES (Isomeric): C1CC2=C(C(=C(C=C2O)O)C3=C(OC4=CC(=CC(=C4C3=O)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)13-22(36)26(30(19)38-23)27-28(37)25-21(35)11-18(33)12-24(25)39-29(27)15-3-7-17(32)8-4-15/h1-8,11-13,23,31-36H,9-10H2/t23-/m0/s1
• InChI Key: KBUYUAWZPKKJRC-QHCPKHFHSA-N
• Popularity: 5 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): 157.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 5.43
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

• MLS002472884
• SMR001396995
• CHEMBL1433872
• BDBM67698
• cid_13941113
• HMS2221D08
• REGID_for_CID_13941113
• 2-(4-hydroxyphenyl)-3-[(2S)-2-(4-hydroxyphenyl)-5,7-bis(oxidanyl)-3,4-dihydro-2H-chromen-8-yl]-5,7-bis(oxidanyl)chromen-4-one
• 3-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyran-4-one
• 3-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• 3-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8985	89.85%
Caco-2	-	0.8735	87.35%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8564	85.64%
OATP2B1 inhibitior	-	0.5621	56.21%
OATP1B1 inhibitior	+	0.8076	80.76%
OATP1B3 inhibitior	+	0.8388	83.88%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.8108	81.08%
BSEP inhibitior	+	0.6697	66.97%
P-glycoprotein inhibitior	+	0.7689	76.89%
P-glycoprotein substrate	-	0.6186	61.86%
CYP3A4 substrate	+	0.6646	66.46%
CYP2C9 substrate	-	0.5831	58.31%
CYP2D6 substrate	-	0.7906	79.06%
CYP3A4 inhibition	+	0.5721	57.21%
CYP2C9 inhibition	+	0.8087	80.87%
CYP2C19 inhibition	+	0.8149	81.49%
CYP2D6 inhibition	-	0.8470	84.70%
CYP1A2 inhibition	+	0.7806	78.06%
CYP2C8 inhibition	+	0.9090	90.90%
CYP inhibitory promiscuity	-	0.6102	61.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6279	62.79%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.7218	72.18%
Skin irritation	-	0.6160	61.60%
Skin corrosion	-	0.9418	94.18%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8137	81.37%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8231	82.31%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7589	75.89%
Acute Oral Toxicity (c)	II	0.3135	31.35%
Estrogen receptor binding	+	0.8145	81.45%
Androgen receptor binding	+	0.8880	88.80%
Thyroid receptor binding	+	0.6116	61.16%
Glucocorticoid receptor binding	+	0.7771	77.71%
Aromatase binding	+	0.5558	55.58%
PPAR gamma	+	0.7458	74.58%
Honey bee toxicity	-	0.8172	81.72%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.7462	74.62%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	97.20%	98.35%
CHEMBL1929	P47989	Xanthine dehydrogenase	97.16%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.60%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.46%	95.64%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	95.10%	83.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.32%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.01%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.90%	98.95%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	91.50%	95.78%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.94%	93.40%
CHEMBL3194	P02766	Transthyretin	90.70%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.72%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	87.90%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.95%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.54%	94.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	86.37%	85.11%
CHEMBL217	P14416	Dopamine D2 receptor	85.72%	95.62%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	84.33%	83.10%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.21%	99.15%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.01%	91.38%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.98%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.38%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.11%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.49%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.03%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.90%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.29%	95.89%
CHEMBL4530	P00488	Coagulation factor XIII	80.01%	96.00%
CHEMBL3438	Q05513	Protein kinase C zeta	80.00%	88.48%

Plants that contains it

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

Cross-Links

• PubChem: 13941113
• NPASS: NPC174086
• ChEMBL: CHEMBL1433872
• LOTUS: LTS0080905
• wikiData: Q105138538