Daphnodorin C

Details

• Internal ID: 1e67a00c-877c-4808-a9f5-1190e9b53767
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,2'S,8'S)-4,5',6-trihydroxy-2',8'-bis(4-hydroxyphenyl)spiro[1-benzofuran-2,9'-2,3,4,8-tetrahydrofuro[2,3-h]chromene]-3-one
• SMILES (Canonical): C1CC2=C(C3=C(C=C2O)OC(C34C(=O)C5=C(C=C(C=C5O4)O)O)C6=CC=C(C=C6)O)OC1C7=CC=C(C=C7)O
• SMILES (Isomeric): C1CC2=C(C3=C(C=C2O)O[C@H]([C@]34C(=O)C5=C(C=C(C=C5O4)O)O)C6=CC=C(C=C6)O)O[C@@H]1C7=CC=C(C=C7)O
• InChI: InChI=1S/C30H22O9/c31-16-5-1-14(2-6-16)22-10-9-19-20(34)13-24-26(27(19)37-22)30(29(38-24)15-3-7-17(32)8-4-15)28(36)25-21(35)11-18(33)12-23(25)39-30/h1-8,11-13,22,29,31-35H,9-10H2/t22-,29-,30+/m0/s1
• InChI Key: ISQNBCHHDNWNEQ-TVNVSJRUSA-N
• Popularity: 6 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): 146.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.89
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• 95733-04-3
• C30-H22-O9
• SCHEMBL1229248
• CHEMBL2273053
• DTXSID60914831
• (2S,2'S,8'S)-4,5',6-trihydroxy-2',8'-bis(4-hydroxyphenyl)spiro[1-benzofuran-2,9'-2,3,4,8-tetrahydrofuro[2,3-h]chromene]-3-one
• (2S,8S,9S)-4',5,6'-trihydroxy-2,8-bis(4-hydroxyphenyl)spiro[2,3,4,8-tetrahydrofuro[2,3-h]chromene-9,2'-benzofuran]-3'-one
• [3',4'-Dihydro-4,5',6-trihydroxy-2',8'-bis(4-hydroxyphenyl)spiro[benzofuran-2(3H),9'(8'H)-[2H]furo[2,3-h][1]benzopyran-3-one, (8'-S-cis)
• 4,5',6-Trihydroxy-2',8'-bis(4-hydroxyphenyl)-3',4'-dihydro-2'H,3H,8'H-spiro[1-benzofuran-2,9'-furo[2,3-h][1]benzopyran]-3-one
• Sprio(benzofuran-2(3H),9'(8'H)-(2H)furo(2,3-h)(1)benzopyran)-3-one, 3',4'-dihydro-4,5',6-trihydroxy-2',8'-bis(4-hydroxyphenyl)-, (8'S-cis)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9378	93.78%
Caco-2	-	0.8724	87.24%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8390	83.90%
OATP2B1 inhibitior	-	0.5766	57.66%
OATP1B1 inhibitior	+	0.8372	83.72%
OATP1B3 inhibitior	+	0.8954	89.54%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8108	81.08%
BSEP inhibitior	+	0.7569	75.69%
P-glycoprotein inhibitior	+	0.7704	77.04%
P-glycoprotein substrate	-	0.7354	73.54%
CYP3A4 substrate	+	0.6412	64.12%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.7380	73.80%
CYP3A4 inhibition	+	0.5522	55.22%
CYP2C9 inhibition	+	0.6115	61.15%
CYP2C19 inhibition	-	0.5201	52.01%
CYP2D6 inhibition	-	0.8001	80.01%
CYP1A2 inhibition	-	0.5802	58.02%
CYP2C8 inhibition	+	0.7253	72.53%
CYP inhibitory promiscuity	-	0.6437	64.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4396	43.96%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.7754	77.54%
Skin irritation	-	0.6984	69.84%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7416	74.16%
Micronuclear	+	0.5459	54.59%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8194	81.94%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5961	59.61%
Acute Oral Toxicity (c)	III	0.4473	44.73%
Estrogen receptor binding	+	0.7937	79.37%
Androgen receptor binding	+	0.7810	78.10%
Thyroid receptor binding	+	0.5863	58.63%
Glucocorticoid receptor binding	+	0.7768	77.68%
Aromatase binding	+	0.5749	57.49%
PPAR gamma	+	0.7355	73.55%
Honey bee toxicity	-	0.7908	79.08%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	-	0.3635	36.35%

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	99.46%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.02%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.51%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.31%	93.40%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.40%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.64%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.40%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	92.40%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.02%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.32%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.27%	96.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	89.48%	85.11%
CHEMBL3194	P02766	Transthyretin	87.06%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.48%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.47%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.92%	93.99%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.90%	85.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.51%	95.78%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.43%	97.33%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.04%	89.67%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	81.64%	82.50%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	81.55%	83.14%
CHEMBL2535	P11166	Glucose transporter	81.03%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.72%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.71%	92.94%
CHEMBL4530	P00488	Coagulation factor XIII	80.56%	96.00%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	80.49%	95.55%

Plants that contains it

• Acer caudatifolium
• Aconitum heterophyllum
• Astragalus sinicus
• Baccharis macraei
• Cynoglossum lanceolatum
• 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: 72428
• NPASS: NPC82330
• LOTUS: LTS0204439
• wikiData: Q82885667