Ancistrobrevine L - Compound Card

Ancistrobrevine L

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Ancistrobrevine L

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cccc2c1c(OC)cc(c2c1c(O)cc(c2c1C[C@@H](C)N([C@H]2C)C)O)C
InChI InChI=1S/C25H29NO4/c1-13-10-21(30-6)25-16(8-7-9-20(25)29-5)22(13)24-17-11-14(2)26(4)15(3)23(17)18(27)12-19(24)28/h7-10,12,14-15,27-28H,11H2,1-6H3/t14-,15+/m1/s1
InChIKey PMKSBAPXGBZLQS-CABCVRRESA-N
Formula C25H29NO4
HBA 5
HBD 2
MW 407.51
Rotatable Bonds 3
TPSA 62.16
LogP 5.18
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 407.21
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • Fayez S, Li Jun, et al. (2019). A near-complete series of four atropisomeric Jozimine A2‐Type naphthylisoquinoline dimers with antiplasmodial and cytotoxic activities and related alkaloids from Ancistrocladus abbreviatus. Journal of Natural Products,2019, 82(11). [View]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 407.51 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.880
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.030
Plasma Protein Binding
79.99
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.160
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.990
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.600
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.940
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-30.820
Rat (Acute)
2.410
Rat (Chronic Oral)
2.130
Fathead Minnow
4.910
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
468.660
Hydration Free Energy
-6.710
Log(D) at pH=7.4
3.790
Log(P)
4.25
Log S
-4.44
Log(Vapor Pressure)
-9.4
Melting Point
152.74
pKa Acid
9.07
pKa Basic
9.37
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 0.9620
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9255
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9167
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9105
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8761
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8746
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8715
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8456
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8388
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.8095
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8066
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8044
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8000
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7976
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7831
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7807
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7806
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7746
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7742
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7706
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7677
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7642
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7634
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7633
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7556
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7534
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7504
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7471
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7392
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7337
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7310
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7303
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7274
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7267
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7225
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7208
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7204
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7185
Thiamine-monophosphate kinase O67883 THIL_AQUAE Aquifex aeolicus 3 0.7172
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7168
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7162
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7162
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7159
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7128
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7094
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7076
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7037
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7035

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