Ancistrocladisine B - Compound Card

Ancistrocladisine B

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Ancistrocladisine B

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc2C[C@H](C)N[C@@H](c2c(c1c1c(C)cc(c2c1cccc2OC)OC)O)C
InChI InChI=1S/C25H29NO4/c1-13-10-19(29-5)23-17(8-7-9-18(23)28-4)21(13)24-20(30-6)12-16-11-14(2)26-15(3)22(16)25(24)27/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15+/m0/s1
InChIKey XJKBCFDZMXLQGI-LSDHHAIUSA-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 ileboensis Ancistrocladaceae Plantae 1367080

Showing of synonyms

  • Li J, Seupel R, et al. (2017). Dioncophyllines C2, D2, and F and related naphthylisoquinoline alkaloids from the Congolese Liana Ancistrocladus ileboensis with potent activities against Plasmodium falciparum and against multiple myeloma and leukemia cell lines. Journal of natural products,2017, 80(2), 443-458. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4

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

Antimalarial

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.220
Plasma Protein Binding
78.69
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
8.580
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.530
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.090
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.530
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
-34.430
Rat (Acute)
2.520
Rat (Chronic Oral)
2.110
Fathead Minnow
5.220
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
454.960
Hydration Free Energy
-5.690
Log(D) at pH=7.4
4.180
Log(P)
4.04
Log S
-4.49
Log(Vapor Pressure)
-8.97
Melting Point
156.04
pKa Acid
10.02
pKa Basic
9.71
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 0.9490
Renin P00797 RENI_HUMAN Homo sapiens 3 0.9306
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9218
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8964
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8934
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8804
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8471
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8443
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8262
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8247
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8206
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8203
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8147
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8000
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7967
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7827
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7804
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7760
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7750
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7748
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7664
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7635
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7612
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7607
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7606
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7521
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7498
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7468
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7404
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7403
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7363
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7340
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7297
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7263
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7256
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7248
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7218
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7208
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7201
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7186
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7149
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7129
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7113
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7075
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7063
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7020
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7005
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7002

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