Daphnoline

Details

• Internal ID: 71f1191b-122f-49ab-80e9-3e49eff4c777
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (1R,14S)-20,25-dimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-3(36),4,6,9(35),10,12(34),18,20,22(33),24,26,31-dodecaene-6,21-diol
• SMILES (Canonical): CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=CC(=C(C=C7CCN6)OC)O3)O)O)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@@H]6C7=CC(=C(C=C7CCN6)OC)O3)O)O)OC
• InChI: InChI=1S/C35H36N2O6/c1-37-13-11-23-18-32(41-3)34(39)35-33(23)27(37)15-20-4-7-24(8-5-20)42-29-16-21(6-9-28(29)38)14-26-25-19-31(43-35)30(40-2)17-22(25)10-12-36-26/h4-9,16-19,26-27,36,38-39H,10-15H2,1-3H3/t26-,27+/m1/s1
• InChI Key: AKGWXHYTRBFUAD-SXOMAYOGSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₃₆N₂O₆
• Molecular Weight: 580.70 g/mol
• Exact Mass: 580.25733687 g/mol
• Topological Polar Surface Area (TPSA): 92.60 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 6.21
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• Trilobamin
• Trilobamine
• Daphnoline [MI]
• (+)-Daphnoline
• 479-36-7
• UNII-1I098GKO6U
• Daphnoline (R,S)
• 1I098GKO6U
• 6,6'-dimethoxy-2-methyloxyacanthan-7,12'-diol
• CHEBI:4323
• 2H-1,24:12,15-Dietheno-6,10-metheno-16H-pyrido(2',3':17,18)(1,10)dioxacycloeicosino(2,3,4-ij)isoquinoline-9,22-diol, 3,4,4a,5,16a,17,18,19-octahydro-21,26-dimethoxy-17-methyl-, (4aR,16aS)-
• 2H-1,24:12,15-Dietheno-6,10-metheno-16H-pyrido(2',3':17,18)(1,10)dioxacycloeicosino(2,3,4-ij)isoquinoline-9,22-diol, 3,4,4a,5,16a,17,18,19-octahydro-21,26-dimethoxy-17-methyl-, (4ar-(4ar*,16as*))-
• (1R,14S)-20,25-dimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-3(36),4,6,9(35),10,12(34),18,20,22(33),24,26,31-dodecaene-6,21-diol
• AC1L65EA
• AC1Q58F2
• CHEMBL2262848
• BDBM85441
• DTXSID20963961
• NSC93673
• NSC-93673
• C09418
• Q27106337
• (4aR,16aS)-3,4,4a,5,16a,17,18,19-Octahydro-21,26-dimethoxy-17-methyl-2H-1,24:12,15-dietheno-6,10-metheno-16H-pyrido[2',3':17,18][1,10]dioxacycloeicosino[2,3,4-ij]isoquinoline-9,22-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7908	79.08%
Caco-2	-	0.5774	57.74%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Lysosomes	0.6772	67.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9185	91.85%
OATP1B3 inhibitior	+	0.9417	94.17%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9907	99.07%
P-glycoprotein inhibitior	+	0.9232	92.32%
P-glycoprotein substrate	+	0.7313	73.13%
CYP3A4 substrate	+	0.6909	69.09%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	+	0.7102	71.02%
CYP3A4 inhibition	-	0.9272	92.72%
CYP2C9 inhibition	-	0.9394	93.94%
CYP2C19 inhibition	-	0.9392	93.92%
CYP2D6 inhibition	-	0.9464	94.64%
CYP1A2 inhibition	-	0.9322	93.22%
CYP2C8 inhibition	+	0.6109	61.09%
CYP inhibitory promiscuity	-	0.9852	98.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6597	65.97%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9517	95.17%
Skin irritation	-	0.7660	76.60%
Skin corrosion	-	0.9412	94.12%
Ames mutagenesis	+	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8540	85.40%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8791	87.91%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8746	87.46%
Acute Oral Toxicity (c)	III	0.5946	59.46%
Estrogen receptor binding	+	0.8093	80.93%
Androgen receptor binding	+	0.7039	70.39%
Thyroid receptor binding	+	0.6515	65.15%
Glucocorticoid receptor binding	+	0.8126	81.26%
Aromatase binding	+	0.5466	54.66%
PPAR gamma	+	0.6634	66.34%
Honey bee toxicity	-	0.7376	73.76%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.6661	66.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.22%	91.11%
CHEMBL2056	P21728	Dopamine D1 receptor	95.54%	91.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.49%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.04%	94.45%
CHEMBL217	P14416	Dopamine D2 receptor	93.93%	95.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.64%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.01%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.49%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	90.48%	91.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.71%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.40%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.66%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.23%	94.00%
CHEMBL4208	P20618	Proteasome component C5	85.87%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.56%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.28%	89.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.27%	97.09%
CHEMBL2535	P11166	Glucose transporter	85.16%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.48%	89.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.27%	90.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.00%	90.71%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	82.91%	91.79%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.91%	85.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.55%	95.78%

Plants that contains it

• Cocculus orbiculatus
• Cocculus pendulus
• Daphnandra micrantha
• Glycyrrhiza inflata
• Guatteria guianensis
• Pachygone dasycarpa
• Pachygone loyaltiensis
• Pycnarrhena ozantha

Cross-Links

• PubChem: 261477
• NPASS: NPC175890
• LOTUS: LTS0157702
• wikiData: Q27106337