ANPDB

Select a section from the left sidebar

4′-O-demethyldioncophylline A

Family: Plantae - Ancistrocladaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid

Canonical Smiles	COc1cccc2c1c(O)cc(c2c1ccc2c(c1O)[C@@H](C)N[C@@H](C2)C)C
InChI	InChI=1S/C23H25NO3/c1-12-10-18(25)22-16(6-5-7-19(22)27-4)20(12)17-9-8-15-11-13(2)24-14(3)21(15)23(17)26/h5-10,13-14,24-26H,11H2,1-4H3/t13-,14-/m1/s1
InChIKey	FFCNRMUGVLXZTG-ZIAGYGMSSA-N
Formula	C₂₃H₂₅NO₃
HBA	4
HBD	3
MW	363.46
Rotatable Bonds	2
TPSA	61.72
LogP	4.83
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	363.18
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus ileboensis	Ancistrocladaceae	Plantae	1367080

Showing of synonyms

Li J, Seupel R, et al. (2017). Jozilebomines A and B, Naphthylisoquinoline Dimers from the Congolese Liana Ancistrocladus ileboensis, with Antiausterity Activities against the PANC-1 Human Pancreatic Cancer Cell Line.. Journal of natural products,2017, 80(10), 2807-2817. [View] [PubMed]

Pubchem: 59095068

Chembl: CHEMBL4074551

No compound-protein relationship available.

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4

Level: 1

Mol. Weight: 363.46 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 363.46 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 363.46 g/mol

Antimalarial

Absorption

Caco-2 (logPapp): -4.97
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.900
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.49

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.020
Plasma Protein Binding: 86.95
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.260
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.630
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.730
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.300
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -7.510
Rat (Acute): 2.550
Rat (Chronic Oral): 2.150
Fathead Minnow: 4.820
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 456.080
Hydration Free Energy: -8.860
Log(D) at pH=7.4: 4.160
Log(P): 4.12
Log S: -4.42
Log(Vapor Pressure): -8.6
Melting Point: 181.49
pKa Acid: 9.08
pKa Basic: 8.62

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9496
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9493
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9127
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9088
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.9085
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9070
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8992
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8960
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8757
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.8696
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.8529
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8463
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.8428
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8402
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.8398
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8395
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.8345
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8340
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.8281
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8256
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8119
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8112
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8061
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8018
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7981
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7923
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7874
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7850
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7832
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.7831
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7810
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7783
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7780
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7722
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7698
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7696
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7652
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7634
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7623
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7536
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7496
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7494
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7488
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7483
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7462
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7460
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7454
Alpha-1-acid glycoprotein 2	P19652	A1AG2_HUMAN	Homo sapiens	3	0.7413
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7406
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7401
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7364
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7359
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7356
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7276
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7263
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7261
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7196
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7190
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7131
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7112
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7103
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7100
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7082
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7069
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7069
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7017

Download SDF