Ancistrocladisine A - Compound Card

Ancistrocladisine A

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Ancistrocladisine A

Structure
Zoomed Structure
  • Family: Plantae - Dioncophyllaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1c2[C@@H](C)N[C@H](Cc2ccc1c1c(C)cc(c2c1cccc2OC)OC)C
InChI InChI=1S/C25H29NO3/c1-14-12-21(28-5)24-18(8-7-9-20(24)27-4)22(14)19-11-10-17-13-15(2)26-16(3)23(17)25(19)29-6/h7-12,15-16,26H,13H2,1-6H3/t15-,16+/m0/s1
InChIKey CFXCQVGAPLLQEX-JKSUJKDBSA-N
Formula C25H29NO3
HBA 4
HBD 1
MW 391.51
Rotatable Bonds 4
TPSA 39.72
LogP 5.44
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 391.21
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ileboensis Ancistrocladaceae Plantae 1367080
2 Ancistrocladus ileboensis Dioncophyllaceae 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]
Pubchem: 132500911

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 391.51 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 391.51 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 391.51 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.89
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.39
Plasma Protein Binding
77.14
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
8.45
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.05
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.03
Micronucleos
Toxic
NR-AhR
Safe
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
-23.98
Rat (Acute)
3.01
Rat (Chronic Oral)
1.81
Fathead Minnow
5.74
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
459.22
Hydration Free Energy
-6.39
Log(D) at pH=7.4
4.03
Log(P)
4.94
Log S
-4.38
Log(Vapor Pressure)
-8.13
Melting Point
128.05
pKa Acid
12.34
pKa Basic
9.96
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 0.9632
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9439
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9019
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8950
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8707
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8698
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8566
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8461
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8397
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8370
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8344
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8276
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8261
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8204
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8179
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8114
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8110
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8014
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8011
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8000
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.8000
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7935
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7854
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7850
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7844
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7795
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7771
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7758
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7755
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7750
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7743
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7739
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7702
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.7698
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7693
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7693
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7691
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7655
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7600
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7590
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7585
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7553
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7537
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7437
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7417
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7385
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7374
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7366
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7352
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 4 0.7347
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7334
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7331
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7327
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7323
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7306
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7286
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7261
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7248
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7223
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7197
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7189
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7182
Aminoglycoside 3'-phosphotransferase P0A3Y5 KKA3_ENTFL Enterococcus faecalis 3 0.7153
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7146
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7121
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7080
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7068
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7067
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7059
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7046
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7033
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7016

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