Ancistrocladinium A - Compound Card

Ancistrocladinium A

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Ancistrocladinium A

Structure
Zoomed Structure
  • Family: Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Quinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1)C[C@@H]([N+](=C2C)c1ccc(c2c1cc(C)cc2OC)OC)C
InChI InChI=1S/C26H30NO4/c1-15-10-20-21(8-9-22(29-5)26(20)23(11-15)30-6)27-16(2)12-18-13-19(28-4)14-24(31-7)25(18)17(27)3/h8-11,13-14,16H,12H2,1-7H3/q+1/t16-/m0/s1
InChIKey JKTBSIJVOXMOGK-INIZCTEOSA-N
Formula C26H30NO4+
HBA 4
HBD 0
MW 420.53
Rotatable Bonds 5
TPSA 39.93
LogP 5.28
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 1
Fraction CSP3 0.35
Exact Mass 420.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus congolensis Ancistrocladaceae Plantae 714097

Showing of synonyms

  • Bringmann G, Spuziak J, et al. (2008). Six naphthylisoquinoline alkaloids and a related benzopyranone from a Congolese Ancistrocladus species related to Ancistrocladus congolensis. Phytochemistry,2008, 69(4), 1065-1075. [View] [PubMed]
Pubchem: 15984091
Nmrshiftdb2: 70030533

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2[N+](=C3)CCc(c34)cccc4

Level: 1

Mol. Weight: 258.34 g/mol

Structure

SMILES: C1=[NH+]CCc(c12)cccc2

Level: 0

Mol. Weight: 132.19 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 128.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.24
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.640
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.290
Plasma Protein Binding
67.71
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
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
9.360
Organic Cation Transporter 2
Non-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)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.370
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
10.040
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
Toxic
T. Pyriformis
-54.000
Rat (Acute)
2.840
Rat (Chronic Oral)
1.860
Fathead Minnow
5.820
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
479.990
Hydration Free Energy
-3.830
Log(D) at pH=7.4
4.070
Log(P)
3.23
Log S
-2.92
Log(Vapor Pressure)
-7.65
Melting Point
124.65
pKa Acid
11.59
pKa Basic
7.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9697
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9697
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9458
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9458
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9236
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9236
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9187
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9187
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9069
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9069
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8999
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8999
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8943
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8943
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8640
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8640
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8540
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8540
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8464
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8464
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8322
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8322
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8268
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8268
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8258
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8258
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8126
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8126
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8117
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8117
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7946
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7946
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7904
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7904
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7895
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7895
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7779
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7779
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7772
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7772
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7726
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7726
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7701
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7701
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7699
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7699
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7684
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7684
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7649
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7649
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7634
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7634
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7615
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7615
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7610
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7610
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7594
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7594
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7586
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7586
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7584
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7584
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7561
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7561
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7561
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7561
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7553
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7553
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7529
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7529
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7501
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7501
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7466
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7466
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7448
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7448
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7427
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7427
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7426
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7426
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7397
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7397
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7374
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7374
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7357
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7357
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7345
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7345
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7336
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7336
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7335
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7335
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7318
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7318
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7301
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7301
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7279
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7279
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7275
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7275
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.7269
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.7269
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7267
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7267
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7257
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7257
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7239
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7239
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7232
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7232
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7221
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7221
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7192
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7192
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7168
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7168
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7163
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7163
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7127
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7127
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7114
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7114
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7109
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7109
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7107
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7107
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7088
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7088
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7074
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7074
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7065
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7065
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7065
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7065
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7035
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7035
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7017
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7017
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 3 0.7016
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 3 0.7016
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7009
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7009

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