Ancistroealaine C - Compound Card

Ancistroealaine C

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Ancistroealaine C

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(C)cc2c1c(O)ccc2c1c(O)cc(c2c1C[C@@H](C)N[C@H]2C)O
InChI InChI=1S/C23H25NO4/c1-11-7-15-14(5-6-17(25)23(15)20(8-11)28-4)22-16-9-12(2)24-13(3)21(16)18(26)10-19(22)27/h5-8,10,12-13,24-27H,9H2,1-4H3/t12-,13+/m1/s1
InChIKey JOXWHCNNDTWJPX-OLZOCXBDSA-N
Formula C23H25NO4
HBA 5
HBD 4
MW 379.46
Rotatable Bonds 2
TPSA 81.95
LogP 4.54
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 379.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098
2 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098

Showing of synonyms

  • Tshitenge DT, Bruhn T, et al. (2019). Ealamines A-H, a Series of Naphthylisoquinolines with the Rare 7,8'-Coupling Site, from the Congolese Liana <i>Ancistrocladus ealaensis</i>, Targeting Pancreatic Cancer Cells.. Journal of natural products,2019, 82(11), 3150-3164. [View] [PubMed]
  • Tshitenge DT, Feineis D, et al. (2018). Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana Ancistrocladus ealaensis with Antiparasitic and Antileukemic Activities.. Journal of natural products,2018, 81(4), 918-933. [View] [PubMed]
Pubchem: 145979137

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 379.46 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 379.46 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 379.46 g/mol

Antileukemia
Antiparasitic

Absorption

Caco-2 (logPapp)
-5.35
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.070
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.020
Plasma Protein Binding
81.31
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.040
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.690
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.550
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.020
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-11.430
Rat (Acute)
2.310
Rat (Chronic Oral)
2.330
Fathead Minnow
4.660
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
481.010
Hydration Free Energy
-8.980
Log(D) at pH=7.4
3.710
Log(P)
3.88
Log S
-4.49
Log(Vapor Pressure)
-8.39
Melting Point
203.49
pKa Acid
8.42
pKa Basic
8.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9246
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9185
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9143
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9057
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8980
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8912
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8836
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8433
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8365
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8344
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8250
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8205
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8097
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7923
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7916
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7912
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7875
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7842
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7817
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7749
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7633
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7499
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7474
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7402
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7394
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7385
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7358
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7347
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7334
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7302
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7295
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7229
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7226
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7209
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7173
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7139
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7114
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7110
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7107
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7106
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7089
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7079
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7060
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7060
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7053
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7051
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7024
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7013

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