6,5'-O,O-didemethylancistroealaine A - Compound Card

6,5'-O,O-didemethylancistroealaine A

Select a section from the left sidebar

6,5'-O,O-didemethylancistroealaine A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(O)c(c2c1C(=N[C@H](C2)C)C)c1ccc(c2c1cc(C)cc2OC)O
InChI InChI=1S/C24H25NO4/c1-12-8-16-15(6-7-18(26)24(16)20(9-12)28-4)23-17-10-13(2)25-14(3)22(17)21(29-5)11-19(23)27/h6-9,11,13,26-27H,10H2,1-5H3/t13-/m0/s1
InChIKey LHRYTRIXHHUCIK-ZDUSSCGKSA-N
Formula C24H25NO4
HBA 5
HBD 2
MW 391.47
Rotatable Bonds 3
TPSA 71.28
LogP 5.0
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 391.18
Number of Lipinski Rule Violations 0
# 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: 135550839

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)C=NCC4

Level: 1

Mol. Weight: 391.47 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 391.47 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 391.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.760
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.380
Plasma Protein Binding
86.99
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.190
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.170
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
-14.310
Rat (Acute)
2.230
Rat (Chronic Oral)
2.440
Fathead Minnow
5.230
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
480.880
Hydration Free Energy
-6.520
Log(D) at pH=7.4
4.080
Log(P)
4.86
Log S
-6.44
Log(Vapor Pressure)
-8.13
Melting Point
185.53
pKa Acid
9.46
pKa Basic
7.45
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 0.9431
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9431
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9167
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9167
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9148
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9148
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9138
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9138
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9050
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9050
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8982
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8982
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8726
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8726
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8622
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8622
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8510
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8510
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8474
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8474
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8363
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8363
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8312
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8312
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8233
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8233
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8044
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8044
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8029
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8029
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8011
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8011
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8005
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8005
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7813
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7813
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7795
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7795
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7748
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7748
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7736
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7736
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7713
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7713
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7662
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7662
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7648
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7648
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7567
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7567
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7562
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7562
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7509
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7509
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7505
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7505
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7441
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7441
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7429
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7429
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7425
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7425
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7422
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7422
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7404
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7404
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7397
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7397
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7385
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7385
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7369
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7369
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7344
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7344
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7342
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7342
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7342
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7342
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7316
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7316
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7273
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7273
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7271
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7271
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7266
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7266
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7264
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7264
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7258
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7258
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7257
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7257
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7256
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7256
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7245
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7245
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7229
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7229
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7220
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7220
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7216
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7216
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7180
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7180
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7148
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7148
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7129
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7129
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7122
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7122
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7106
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7106
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7096
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7096
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7092
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7092
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7077
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7077
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7047
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7047
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7040
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7040
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7004
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7004
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7004
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7004
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7003
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7003

Download SDF