Ancistrolikokine J - Compound Card

Ancistrolikokine J

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Ancistrolikokine J

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Quinoline Alkaloid
Canonical Smiles COc1cc(O)c(c2c1c(C)nc(c2)C)c1ccc(c2c1cc(C)cc2OC)O
InChI InChI=1S/C24H23NO4/c1-12-8-16-15(6-7-18(26)24(16)20(9-12)28-4)23-17-10-13(2)25-14(3)22(17)21(29-5)11-19(23)27/h6-11,26-27H,1-5H3
InChIKey GTRPNZGNZRKAOY-UHFFFAOYSA-N
Formula C24H23NO4
HBA 5
HBD 2
MW 389.45
Rotatable Bonds 3
TPSA 71.81
LogP 5.41
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 389.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus likoko Ancistrocladaceae Plantae 714102

Showing of synonyms

  • Fayez S, Feineis D, et al. (2018). Ancistrolikokine I and further 5,8′-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko and their cytotoxic activities against drug-sensitive and multidrug resistant human leukemia cells.. Fitoterapia,2018, 129, 114-125. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)cncc4

Level: 1

Mol. Weight: 389.45 g/mol

Structure

SMILES: c1cncc(c12)cccc2

Level: 0

Mol. Weight: 389.45 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 389.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.870
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.660
Plasma Protein Binding
91.39
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.930
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.840
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.720
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.370
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
-13.640
Rat (Acute)
2.450
Rat (Chronic Oral)
2.330
Fathead Minnow
5.540
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
511.200
Hydration Free Energy
-7.610
Log(D) at pH=7.4
4.130
Log(P)
5.08
Log S
-6.61
Log(Vapor Pressure)
-8.89
Melting Point
215.36
pKa Acid
9.37
pKa Basic
7.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9299
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9238
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8804
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8753
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8395
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8274
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8228
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8202
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8143
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8101
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7889
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7888
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7837
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7709
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7706
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7544
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7542
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7516
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7437
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7398
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7344
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7333
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7299
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7290
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7254
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7236
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7208
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7175
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7149
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7132
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7126
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7110
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7105

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