Ancistrotanzanine A - Compound Card

Ancistrotanzanine A

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Ancistrotanzanine A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1c1c(C)cc3c(c1O)c(OC)ccc3)C[C@@H](N=C2C)C
InChI InChI=1S/C25H27NO4/c1-13-10-16-8-7-9-18(28-4)23(16)25(27)21(13)24-17-11-14(2)26-15(3)22(17)19(29-5)12-20(24)30-6/h7-10,12,14,27H,11H2,1-6H3/t14-/m0/s1
InChIKey QGIHYQPVZRSTNP-AWEZNQCLSA-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 tanzaniensis Ancistrocladaceae Plantae 714107

Showing of synonyms

  • Bringmann G, Dreyer M, et al. (2003). Ancistrotanzanine A, the first 5,3'-coupled naphthylisoquinoline alkaloid, and two further, 5,8'-linked related compounds from the newly described species Ancistrocladus tanzaniensis. Journal of Natural Products,2003,66(9),1159-1165. [View] [PubMed]
Pubchem: 10319100
Chebi: 65406
Nmrshiftdb2: 70070701
Metabolights: MTBLC65406

No compound-protein relationship available.

Structure

SMILES: C1CN=Cc(c12)cccc2-c(c3)ccc(c34)cccc4

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

Antiprotozoal

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.530
Plasma Protein Binding
89.51
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
Non-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
5.810
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.130
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.660
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.190
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
-28.710
Rat (Acute)
2.550
Rat (Chronic Oral)
2.250
Fathead Minnow
5.400
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
497.650
Hydration Free Energy
-5.270
Log(D) at pH=7.4
3.750
Log(P)
5.08
Log S
-6.79
Log(Vapor Pressure)
-8.16
Melting Point
156.15
pKa Acid
9.25
pKa Basic
8.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9424
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9424
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9260
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9260
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8920
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8920
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8782
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8782
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8717
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8717
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8694
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8694
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8628
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8628
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8619
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8619
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8594
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8594
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8585
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8585
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8578
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8578
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8549
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8549
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8504
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8504
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8408
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8408
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8246
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8246
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8131
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8131
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8112
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8112
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8083
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8083
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8058
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8058
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8056
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8056
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8045
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8045
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8003
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8003
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7994
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7994
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7892
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7892
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7865
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7865
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7862
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7862
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7859
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7859
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7833
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7833
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7750
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7750
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7730
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7730
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7725
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7725
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7631
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7631
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7623
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7623
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7609
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7609
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 4 0.7593
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 4 0.7593
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7587
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7587
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7531
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7531
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7450
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7450
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
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7410
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7410
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7388
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7388
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7383
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7383
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7304
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7304
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7281
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7281
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7274
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7274
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7263
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7263
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7256
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7256
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7255
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7255
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7246
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7246
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7240
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7240
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7238
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7238
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7228
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7228
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7204
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7204
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7197
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7197
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7196
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7196
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7195
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7195
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7178
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7178
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7170
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7170
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7159
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7159
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7148
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7148
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7127
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7127
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7125
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7125
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7116
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7116
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7113
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7113
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7110
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7110
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7105
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7105
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7097
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7097
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7094
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7094
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7094
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7094
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7084
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7084
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7084
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7084
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7058
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7058
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7054
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7054
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7038
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7038
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7036
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7036
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7030
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7030

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