O,N-dimethylancistrocladine - Compound Card

O,N-dimethylancistrocladine

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O,N-dimethylancistrocladine

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1c1c(C)cc(c3c1cccc3OC)OC)C[C@@H](N([C@H]2C)C)C
InChI InChI=1S/C27H33NO4/c1-15-12-21(30-6)26-18(10-9-11-20(26)29-5)24(15)27-19-13-16(2)28(4)17(3)25(19)22(31-7)14-23(27)32-8/h9-12,14,16-17H,13H2,1-8H3/t16-,17-/m0/s1
InChIKey KKJVVBRCACGMIS-IRXDYDNUSA-N
Formula C27H33NO4
HBA 5
HBD 0
MW 435.56
Rotatable Bonds 5
TPSA 40.16
LogP 5.79
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 435.24
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. (2004). Ancistrotanzanine C and related 5,1'- and 7,3'-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis. Journal of Natural Products,2004,67(5),743-748. [View] [PubMed]
Pubchem: 11224334
Nmrshiftdb2: 80000281

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4

Level: 1

Mol. Weight: 435.56 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 435.56 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 435.56 g/mol

Antiprotozoal

Absorption

Caco-2 (logPapp)
-5.14
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.760
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.140
Plasma Protein Binding
70.51
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
Non-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
9.520
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.780
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.180
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.780
Micronucleos
Toxic
NR-AhR
Safe
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
-90.580
Rat (Acute)
3.080
Rat (Chronic Oral)
1.800
Fathead Minnow
5.830
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
479.190
Hydration Free Energy
-3.340
Log(D) at pH=7.4
4.020
Log(P)
5.14
Log S
-4.7
Log(Vapor Pressure)
-8.72
Melting Point
122.88
pKa Acid
11.8
pKa Basic
9.93
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 0.9695
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9695
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9298
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9298
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9066
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9066
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8987
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8987
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8654
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8654
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8360
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8360
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8160
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8160
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8023
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8023
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8002
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8002
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7975
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7975
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7964
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7964
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7956
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7956
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7936
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7936
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7901
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7901
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7861
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7861
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7771
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7771
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7594
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7594
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7548
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7548
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7500
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7500
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7487
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7487
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7471
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7471
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7432
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7432
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7431
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7431
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7410
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7410
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7368
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7368
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7356
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7356
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7346
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7346
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7342
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7342
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7329
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7329
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7295
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7295
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7257
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7257
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7241
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7241
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7234
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7234
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7220
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7220
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7199
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7199
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7184
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7184
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7171
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7171
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7163
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7163
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7152
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7152
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7064
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7064
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7053
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7053
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7043
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7043
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7033
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7033
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7031
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7031
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7009
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7009

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