Dioncoline A - Compound Card

Dioncoline A

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Dioncoline A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cccc2c1c(OC)cc(c2c1ccc2c(c1O)[C@H](C)N([C@@H](C2)C)C)C
InChI InChI=1S/C25H29NO3/c1-14-12-21(29-6)24-18(8-7-9-20(24)28-5)22(14)19-11-10-17-13-15(2)26(4)16(3)23(17)25(19)27/h7-12,15-16,27H,13H2,1-6H3/t15-,16+/m1/s1
InChIKey ZSYADESMHZOJRK-CVEARBPZSA-N
Formula C25H29NO3
HBA 4
HBD 1
MW 391.51
Rotatable Bonds 3
TPSA 41.93
LogP 5.48
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 391.21
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • Fayez S, Li Jun, et al. (2019). A near-complete series of four atropisomeric Jozimine A2‐Type naphthylisoquinoline dimers with antiplasmodial and cytotoxic activities and related alkaloids from Ancistrocladus abbreviatus. Journal of Natural Products,2019, 82(11). [View]
Pubchem: 163019168

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 391.51 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 391.51 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 391.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.08
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
83.14
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.740
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.540
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.740
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.580
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
-20.560
Rat (Acute)
2.860
Rat (Chronic Oral)
1.900
Fathead Minnow
5.120
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
453.870
Hydration Free Energy
-6.540
Log(D) at pH=7.4
3.870
Log(P)
4.76
Log S
-4.22
Log(Vapor Pressure)
-9.03
Melting Point
139.16
pKa Acid
9.75
pKa Basic
9.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9525
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9468
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9210
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8944
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8919
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8878
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8669
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8558
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8539
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8517
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8469
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8458
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8406
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8328
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8303
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8229
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8127
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8092
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8080
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7973
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7969
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7946
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7893
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7886
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7885
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7852
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7823
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7808
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7786
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7708
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7681
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7674
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7650
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7607
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7547
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7506
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7490
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7482
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7462
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7454
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7441
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7439
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7437
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7423
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7415
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7383
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7383
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7339
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7338
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7324
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7323
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7251
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7245
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7226
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7216
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7191
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7133
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7122
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7120
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7104
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7087
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7085
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7083
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7061
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7050
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7030
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7024
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7001

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