Daphnodorin F

Details

• Internal ID: 795f226a-82f7-43ab-8f6c-ecd174be2144
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (1R,5S,13S)-1,9,17,19-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaen-21-one
• SMILES (Canonical): C1CC2=C(C3=C(C=C2O)OC4(C3(C(=O)C5=C(C=C(C=C5O4)O)O)O)C6=CC=C(C=C6)O)OC1C7=CC=C(C=C7)O
• SMILES (Isomeric): C1CC2=C(C3=C(C=C2O)O[C@@]4([C@@]3(C(=O)C5=C(C=C(C=C5O4)O)O)O)C6=CC=C(C=C6)O)O[C@@H]1C7=CC=C(C=C7)O
• InChI: InChI=1S/C30H22O10/c31-16-5-1-14(2-6-16)22-10-9-19-20(34)13-24-26(27(19)38-22)29(37)28(36)25-21(35)11-18(33)12-23(25)39-30(29,40-24)15-3-7-17(32)8-4-15/h1-8,11-13,22,31-35,37H,9-10H2/t22-,29+,30+/m0/s1
• InChI Key: KVPJDVHJFGPPAB-XOHQIPOJSA-N
• Popularity: 1 reference 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): 166.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.99
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• Daphnodorin F
• BDBM50386899

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8743	87.43%
Caco-2	-	0.8832	88.32%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8221	82.21%
OATP2B1 inhibitior	-	0.5689	56.89%
OATP1B1 inhibitior	+	0.8498	84.98%
OATP1B3 inhibitior	-	0.2239	22.39%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7858	78.58%
BSEP inhibitior	+	0.8644	86.44%
P-glycoprotein inhibitior	+	0.7482	74.82%
P-glycoprotein substrate	-	0.6470	64.70%
CYP3A4 substrate	+	0.6518	65.18%
CYP2C9 substrate	-	0.8163	81.63%
CYP2D6 substrate	-	0.7976	79.76%
CYP3A4 inhibition	-	0.6042	60.42%
CYP2C9 inhibition	+	0.5546	55.46%
CYP2C19 inhibition	-	0.6461	64.61%
CYP2D6 inhibition	-	0.8817	88.17%
CYP1A2 inhibition	-	0.8075	80.75%
CYP2C8 inhibition	+	0.7649	76.49%
CYP inhibitory promiscuity	-	0.8123	81.23%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4262	42.62%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.7532	75.32%
Skin irritation	-	0.6801	68.01%
Skin corrosion	-	0.9145	91.45%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6897	68.97%
Micronuclear	+	0.5859	58.59%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6600	66.00%
Acute Oral Toxicity (c)	III	0.3241	32.41%
Estrogen receptor binding	+	0.8202	82.02%
Androgen receptor binding	+	0.8063	80.63%
Thyroid receptor binding	+	0.5941	59.41%
Glucocorticoid receptor binding	+	0.7334	73.34%
Aromatase binding	+	0.6463	64.63%
PPAR gamma	+	0.6821	68.21%
Honey bee toxicity	-	0.8257	82.57%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.8422	84.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL280	P45452	Matrix metalloproteinase 13	13170 nM	IC50	PMID: 22658537
CHEMBL283	P08254	Matrix metalloproteinase 3	22300 nM	IC50	PMID: 22658537
CHEMBL321	P14780	Matrix metalloproteinase 9	21240 nM	IC50	PMID: 22658537
CHEMBL333	P08253	Matrix metalloproteinase-2	23280 nM	IC50	PMID: 22658537

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.32%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.96%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.58%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.64%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.64%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.29%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.47%	89.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	92.04%	85.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.00%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.55%	99.23%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.49%	96.12%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.19%	95.78%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.52%	85.00%
CHEMBL3194	P02766	Transthyretin	85.24%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.13%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.09%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.46%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	83.64%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.64%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.53%	96.38%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	83.13%	82.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.09%	92.94%
CHEMBL238	Q01959	Dopamine transporter	82.77%	95.88%
CHEMBL217	P14416	Dopamine D2 receptor	82.39%	95.62%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.31%	93.04%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.20%	90.93%
CHEMBL2535	P11166	Glucose transporter	81.20%	98.75%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.48%	89.67%
CHEMBL340	P08684	Cytochrome P450 3A4	80.20%	91.19%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	80.06%	92.50%

Plants that contains it

• Acer caudatifolium
• Aconitum heterophyllum
• Astragalus sinicus
• Baccharis macraei
• Cynoglossum lanceolatum
• Daphne acutiloba
• 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: 70688394
• NPASS: NPC8704
• ChEMBL: CHEMBL2048507
• LOTUS: LTS0039515
• wikiData: Q105146647