5-epi-ancistectorine A2 - Compound Card

5-epi-ancistectorine A2

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5-epi-ancistectorine A2

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(O)c2c(c1c1c(C)cc(c3c1cccc3OC)OC)C[C@H](N[C@@H]2C)C
InChI InChI=1S/C25H29NO4/c1-13-10-20(29-5)24-16(8-7-9-19(24)28-4)22(13)25-17-11-14(2)26-15(3)23(17)18(27)12-21(25)30-6/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15-/m1/s1
InChIKey RFPVCRMXYDYXBF-HUUCEWRRSA-N
Formula C25H29NO4
HBA 5
HBD 2
MW 407.51
Rotatable Bonds 4
TPSA 59.95
LogP 5.14
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 407.21
Number of Lipinski Rule Violations 1
# 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: 407.51 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.08
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
76.99
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.780
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.040
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.840
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
-34.820
Rat (Acute)
2.530
Rat (Chronic Oral)
2.000
Fathead Minnow
5.380
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
463.030
Hydration Free Energy
-5.910
Log(D) at pH=7.4
4.140
Log(P)
4.39
Log S
-4.7
Log(Vapor Pressure)
-8.85
Melting Point
155.6
pKa Acid
10.34
pKa Basic
10.08
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 0.9674
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9353
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9236
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9144
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8619
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8570
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8321
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8034
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7871
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7826
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7779
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7725
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7704
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7690
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7588
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7564
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7525
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7499
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7458
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7447
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7442
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7442
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7431
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7408
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7394
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7221
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7171
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7171
Thiamine-monophosphate kinase O67883 THIL_AQUAE Aquifex aeolicus 3 0.7145
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7103
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7074
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7069
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7039
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7005
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7003
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7001

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