Ancistrobrevine E - Compound Card

Ancistrobrevine E

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Ancistrobrevine E

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cccc2c1c(OC)cc(c2c1c(O)cc(c2c1C[C@@H](C)N[C@@H]2C)O)C
InChI InChI=1S/C24H27NO4/c1-12-9-20(29-5)24-15(7-6-8-19(24)28-4)21(12)23-16-10-13(2)25-14(3)22(16)17(26)11-18(23)27/h6-9,11,13-14,25-27H,10H2,1-5H3/t13-,14-/m1/s1
InChIKey GODBTWFOMRLWFW-ZIAGYGMSSA-N
Formula C24H27NO4
HBA 5
HBD 3
MW 393.48
Rotatable Bonds 3
TPSA 70.95
LogP 4.84
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 393.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • Fayez S, Feineis D, et al. (2018). Ancistrobrevines E-J and related naphthylisoquinoline alkaloids from the West African liana Ancistrocladus abbreviatus with inhibitory activities against Plasmodium falciparum and PANC-1 human pancreatic cancer cells. Fitoterapia, 2018, 131, 245-259. [View]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4

Level: 1

Mol. Weight: 393.48 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.920
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.100
Plasma Protein Binding
81.22
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
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.650
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.410
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.530
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.550
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-19.540
Rat (Acute)
2.310
Rat (Chronic Oral)
2.150
Fathead Minnow
4.940
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
466.290
Hydration Free Energy
-7.960
Log(D) at pH=7.4
3.790
Log(P)
3.99
Log S
-4.59
Log(Vapor Pressure)
-8.9
Melting Point
177.74
pKa Acid
9.22
pKa Basic
9.47
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 0.9600
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9216
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9148
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9137
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8558
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8534
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8449
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8236
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8015
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8003
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7724
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7698
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7684
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7563
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7524
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7470
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7453
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7415
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7344
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7317
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7305
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7264
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7263
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7183
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7175
Thiamine-monophosphate kinase O67883 THIL_AQUAE Aquifex aeolicus 3 0.7140
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7138
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7117
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7112
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7061
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7020

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