Ancistrobrevidine A - Compound Card

Ancistrobrevidine A

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Ancistrobrevidine 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)c1c(C)cc(c2c1cccc2OC)OC
InChI InChI=1S/C25H27NO4/c1-13-10-20(29-5)25-16(8-7-9-19(25)28-4)22(13)24-17-11-14(2)26-15(3)23(17)21(30-6)12-18(24)27/h7-10,12,14,27H,11H2,1-6H3/t14-/m1/s1
InChIKey NXPYZSTXOUQQLT-CQSZACIVSA-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 abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • Fayez S, Cacciatore A, et al. (2021). Ancistrobrevidines A-C and related naphthylisoquinoline alkaloids with cytotoxic activities against heLa and pancreatic cancer cells, from the liana Ancistrocladus abbreviatus. Bioorganic & Medicinal Chemistry,2021, 30,115950. [View]
Pubchem: 162663176

No compound-protein relationship available.

Structure

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

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

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
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
-2.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.600
Plasma Protein Binding
87.71
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
6.720
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.510
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.140
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.420
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
-28.800
Rat (Acute)
2.600
Rat (Chronic Oral)
2.350
Fathead Minnow
5.520
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
494.460
Hydration Free Energy
-5.270
Log(D) at pH=7.4
4.130
Log(P)
5.14
Log S
-6.64
Log(Vapor Pressure)
-7.91
Melting Point
160.3
pKa Acid
9.8
pKa Basic
7.68
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 0.9623
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9217
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9171
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9122
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8848
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8758
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8710
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8661
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8557
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8520
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8128
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8048
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.8036
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8033
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8014
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7919
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7884
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7875
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7820
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7800
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7757
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7676
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7643
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7635
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7593
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7586
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7580
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7575
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7562
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7559
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7538
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7494
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7471
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7449
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7448
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7418
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7390
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7386
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7369
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7336
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7332
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7320
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7308
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7284
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7276
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7245
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7214
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7205
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7185
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7128
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7115
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7102
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7057
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7026

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