Ancistrocladisine - Compound Card

Ancistrocladisine

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Ancistrocladisine

Structure
Zoomed Structure
  • Family: Plantae - Dioncophyllaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1cc2C[C@@H](C)N=C(c2c(c1c1c(C)cc(c2c1cccc2OC)OC)OC)C
InChI InChI=1S/C26H29NO4/c1-14-11-20(29-5)24-18(9-8-10-19(24)28-4)22(14)25-21(30-6)13-17-12-15(2)27-16(3)23(17)26(25)31-7/h8-11,13,15H,12H2,1-7H3/t15-/m1/s1
InChIKey RYNWWOJXABDOHD-OAHLLOKOSA-N
Formula C26H29NO4
HBA 5
HBD 0
MW 419.52
Rotatable Bonds 5
TPSA 49.28
LogP 5.6
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 419.21
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus robertsoniorum Ancistrocladaceae Plantae 714105
2 Ancistrocladus ileboensis Dioncophyllaceae Plantae 1367080

Showing of synonyms

  • Bringmann G, Teltschika F, et al. (1999). Ancistrobertsonines B, C, and D as well as 1,2-didehydroancistrobertsonine D from Ancistrocladus robertsoniorum. Phytochemistry,1999,52(2),321-332. [View] [PubMed]
  • 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: 375958
Nmrshiftdb2: 70030611

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 419.52 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 419.52 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 419.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.1
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.740
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.680
Plasma Protein Binding
83.45
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.560
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.070
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.110
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.650
Micronucleos
Safe
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
-52.000
Rat (Acute)
2.990
Rat (Chronic Oral)
2.300
Fathead Minnow
5.870
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
507.910
Hydration Free Energy
-3.770
Log(D) at pH=7.4
3.510
Log(P)
5.53
Log S
-6.17
Log(Vapor Pressure)
-7.3
Melting Point
138.37
pKa Acid
11.92
pKa Basic
8.56
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 0.9211
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9211
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9189
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9189
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9058
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9058
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9010
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9010
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8918
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8918
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8715
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8715
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8710
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8710
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8693
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8693
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8362
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8362
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8353
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8353
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8344
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8344
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8225
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8225
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8073
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8073
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8066
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8066
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7967
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7967
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7922
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7922
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7811
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7811
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7808
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7808
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7796
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7796
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7766
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7766
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7736
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7736
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7729
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7729
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7726
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7726
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7720
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7720
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7714
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7714
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7713
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7713
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7678
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7678
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7672
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7672
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7672
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7672
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7645
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7645
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7585
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7585
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7557
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7557
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7519
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7519
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7515
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7515
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7505
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7505
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7476
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7476
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7457
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7457
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7410
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7410
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7406
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7406
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 4 0.7405
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 4 0.7405
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7395
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7395
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7387
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7387
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7354
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7354
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7348
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7348
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7332
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7332
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7330
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7330
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7308
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7308
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7302
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7302
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7298
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7298
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7280
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7280
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7265
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7265
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7259
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7259
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7221
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7221
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7200
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7200
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7186
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7186
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7181
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7181
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7167
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7167
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7127
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7127
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7125
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7125
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7123
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7123
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7121
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7121
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7112
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7112
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7112
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7112
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7111
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7111
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 3 0.7086
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 3 0.7086
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7056
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7056
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7034
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7034
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7031
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7031
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7026
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7026
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7015
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7015
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7009
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7009

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