5-epi-dioncophyllidine C2 - Compound Card

5-epi-dioncophyllidine C2

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5-epi-dioncophyllidine C2

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cccc2c1c(OC)cc(c2c1ccc(c2c1C[C@@H](C)N=C2C)O)C
InChI InChI=1S/C24H25NO3/c1-13-11-21(28-5)24-17(7-6-8-20(24)27-4)22(13)16-9-10-19(26)23-15(3)25-14(2)12-18(16)23/h6-11,14,26H,12H2,1-5H3/t14-/m1/s1
InChIKey MVYQPYKQZNKMIU-CQSZACIVSA-N
Formula C24H25NO3
HBA 4
HBD 1
MW 375.47
Rotatable Bonds 3
TPSA 51.05
LogP 5.29
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 375.18
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • Fayez S, Cacciatore A, et al. (2021). Ancistrobrevidines A-C and related naphthylisoquinoline alkaloids with cytotoxic activities against heLa and pancreatic cancer cells, from the liana Ancistrocladus abbreviatus. Bioorganic & Medicinal Chemistry,2021, 30,115950. [View]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)C=NCC4

Level: 1

Mol. Weight: 375.47 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 375.47 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 375.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.340
Plasma Protein Binding
87.1
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.660
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.880
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.610
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.350
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-8.780
Rat (Acute)
2.540
Rat (Chronic Oral)
2.050
Fathead Minnow
5.260
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
488.800
Hydration Free Energy
-6.330
Log(D) at pH=7.4
3.540
Log(P)
5.29
Log S
-5.97
Log(Vapor Pressure)
-7.95
Melting Point
158.06
pKa Acid
10.08
pKa Basic
9.13
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 0.9679
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9466
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9446
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9306
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9056
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.9035
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8740
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8483
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8468
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8403
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8350
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8174
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8165
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8158
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8146
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8127
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.8070
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8026
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.7914
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7838
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7805
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7782
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7780
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7700
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7686
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7654
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7594
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7589
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7580
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7577
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7544
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7540
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7511
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7491
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7470
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7466
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7446
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7409
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7379
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7377
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7349
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7319
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7276
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7235
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7216
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7192
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7189
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7175
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7171
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7125
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 3 0.7118
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7118
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7109
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7071
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7048
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7014
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7009
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7007

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