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Dioncopeltine A

Family: Plantae - Dioncophyllaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	OCc1cc(OC)c2c(c1c1ccc3c(c1O)[C@@H](C)N[C@@H](C3)C)cccc2O
InChI	InChI=1S/C23H25NO4/c1-12-9-14-7-8-17(23(27)20(14)13(2)24-12)21-15(11-25)10-19(28-3)22-16(21)5-4-6-18(22)26/h4-8,10,12-13,24-27H,9,11H2,1-3H3/t12-,13-/m1/s1
InChIKey	ZQSUAGVTKAZDJV-CHWSQXEVSA-N
Formula	C₂₃H₂₅NO₄
HBA	5
HBD	4
MW	379.46
Rotatable Bonds	3
TPSA	81.95
LogP	4.01
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	379.18
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Triphyophyllum peltatum	Dioncophyllaceae	Plantae	63090

Showing of synonyms

François G, Bringmann G, et al. (1995). Activities of extracts and naphthylisoquinoline alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and Ancistrocladus barteri against Plasmodium berghei (Anka strain) in vitro. Journal of Ethnopharmacology, 1995, 46(2), 115-120. [View]

Pubchem: 185971

Cas: 60158-81-8

Kegg Ligand: C12339

Chebi: 31503

Nmrshiftdb2: 70016117

Metabolights: MTBLC31503

Chembl: CHEMBL222805

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 379.46 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 379.46 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 379.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.4
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.99
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.11

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.98
Plasma Protein Binding: 79.83
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 7.06
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.47
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.52
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.72
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -14.45
Rat (Acute): 2.44
Rat (Chronic Oral): 2.71
Fathead Minnow: 4.53
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 456.03
Hydration Free Energy: -7.98
Log(D) at pH=7.4: 3.49
Log(P): 3.1
Log S: -3.77
Log(Vapor Pressure): -8.23
Melting Point: 164.8
pKa Acid: 8.59
pKa Basic: 8.5

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9295
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9219
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9178
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9119
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.9112
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.9044
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9040
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8853
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8678
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8483
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8478
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8385
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8383
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.8333
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8275
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.8225
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8211
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8124
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8106
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8041
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.8032
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7961
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7917
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7903
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7894
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7808
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7796
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.7793
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7780
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7779
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7759
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7743
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7742
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7732
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7635
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7628
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7618
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7588
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7538
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7527
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7521
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7518
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7436
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7420
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7398
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7362
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7345
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7341
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7327
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7306
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7269
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7233
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7220
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7192
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7188
ADP-ribose glycohydrolase AF_1521	O28751	Y1521_ARCFU	Archaeoglobus fulgidus	4	0.7182
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7173
SRSF protein kinase 1	Q96SB4	SRPK1_HUMAN	Homo sapiens	3	0.7164
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7155
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7143
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7134
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7131
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7126
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7125
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7120
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7119
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7118
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7107
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7103
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	4	0.7098
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7095
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7063
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7052
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7048
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7044
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7043
Mitomycin-binding protein	O05205	O05205_STRLA	Streptomyces lavendulae	2	0.7042
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7040
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7026
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7020
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7015
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7011

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