Ancistrobrevine C - Compound Card

Ancistrobrevine C

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Ancistrobrevine C

Structure
Zoomed Structure
  • Family: Plantae - Dioncophyllaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc2C[C@@H](C)N=C(c2c(c1c1c(C)cc(c2c1cccc2OC)OC)O)C
InChI InChI=1S/C25H27NO4/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/h7-10,12,14,27H,11H2,1-6H3/t14-/m1/s1
InChIKey BHXTVSSYPDITPL-CQSZACIVSA-N
Formula C25H27NO4
HBA 5
HBD 1
MW 405.49
Rotatable Bonds 4
TPSA 60.28
LogP 5.3
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 405.19
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: 136900226
Nmrshiftdb2: 70112102

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCN=C4

Level: 1

Mol. Weight: 405.49 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 405.49 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 405.49 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.540
Plasma Protein Binding
87.26
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.660
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.690
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.130
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.390
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
-28.800
Rat (Acute)
2.660
Rat (Chronic Oral)
2.360
Fathead Minnow
5.490
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
493.880
Hydration Free Energy
-5.220
Log(D) at pH=7.4
3.770
Log(P)
4.96
Log S
-6.51
Log(Vapor Pressure)
-7.96
Melting Point
154.48
pKa Acid
9.41
pKa Basic
7.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Renin P00797 RENI_HUMAN Homo sapiens 3 0.9327
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9234
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9221
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9140
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9136
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9010
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8804
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8720
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8669
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8570
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8372
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8330
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8319
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8252
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8201
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8125
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8052
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8014
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8003
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8000
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7964
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7924
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7922
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7888
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7756
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7744
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7738
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7725
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7684
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7630
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7591
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7573
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7550
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7517
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7487
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7470
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7459
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7431
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7410
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7395
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7357
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7333
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7308
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7290
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7277
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7268
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7267
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7264
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7245
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7217
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7204
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7201
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7185
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7180
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7135
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7119
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7105
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7076
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7075
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7069
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7045
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7008
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7004

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