Ancistrobrevine K - Compound Card

Ancistrobrevine K

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Ancistrobrevine K

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(O)c2c(c1c1c(C)cc(c3c1cccc3OC)O)C[C@H](N[C@H]2C)C
InChI InChI=1S/C24H27NO4/c1-12-9-17(26)23-15(7-6-8-19(23)28-4)21(12)24-16-10-13(2)25-14(3)22(16)18(27)11-20(24)29-5/h6-9,11,13-14,25-27H,10H2,1-5H3/t13-,14+/m1/s1
InChIKey BVIWPSOFLQUWCV-KGLIPLIRSA-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, 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]

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

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.930
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
78.11
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
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.870
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.400
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.270
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.300
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
Toxic
T. Pyriformis
-21.210
Rat (Acute)
2.320
Rat (Chronic Oral)
2.060
Fathead Minnow
5.020
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
467.950
Hydration Free Energy
-7.930
Log(D) at pH=7.4
4.180
Log(P)
4.11
Log S
-4.78
Log(Vapor Pressure)
-8.98
Melting Point
164.01
pKa Acid
9.57
pKa Basic
9.5
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 0.9642
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9481
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9294
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9146
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9125
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8991
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8960
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8921
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8888
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8767
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8644
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8435
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8304
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8212
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8159
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8081
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8025
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7936
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7916
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7910
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7861
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7857
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7683
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7651
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7591
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7583
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7564
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7527
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7490
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7484
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7456
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7406
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7402
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7398
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7392
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7392
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7330
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7318
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7280
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7274
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7267
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7224
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7192
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7123
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7051
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7048
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7038
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7023
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7019

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