Ancistrobrevidine C - Compound Card

Ancistrobrevidine C

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Ancistrobrevidine C

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1c1c(C)cc(c3c1cc(C)cc3O)OC)C[C@H](N=C2C)C
InChI InChI=1S/C26H29NO4/c1-13-8-17-23(14(2)10-20(29-5)25(17)19(28)9-13)26-18-11-15(3)27-16(4)24(18)21(30-6)12-22(26)31-7/h8-10,12,15,28H,11H2,1-7H3/t15-/m1/s1
InChIKey HBGFFJHNNULTDW-OAHLLOKOSA-N
Formula C26H29NO4
HBA 5
HBD 1
MW 419.52
Rotatable Bonds 4
TPSA 60.28
LogP 5.61
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 419.21
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]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 419.52 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 419.52 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 419.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.620
Plasma Protein Binding
88.71
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.530
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.630
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.040
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.530
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
-41.090
Rat (Acute)
2.530
Rat (Chronic Oral)
2.340
Fathead Minnow
5.620
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
506.840
Hydration Free Energy
-4.520
Log(D) at pH=7.4
4.230
Log(P)
5.59
Log S
-7.01
Log(Vapor Pressure)
-7.97
Melting Point
163.92
pKa Acid
10.07
pKa Basic
8.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9248
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9209
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9168
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9129
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8954
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8922
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8876
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8675
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8671
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8571
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8563
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8420
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8352
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8234
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8181
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7783
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7695
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7683
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7677
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7609
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7564
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7555
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7508
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7272
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7268
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7266
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7252
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7242
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7237
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7233
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7220
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7219
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7206
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7202
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7197
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7190
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7188
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7171
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7140
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7139
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7114
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7096
Nicotinamide riboside kinase 1 Q9NWW6 NRK1_HUMAN Homo sapiens 4 0.7084
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7069
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7060
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7049
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7022
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7007

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