Ealamine C - Compound Card

Ealamine C

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Ealamine C

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1c2[C@@H](C)N[C@H](Cc2cc(c1c1ccc(c2c1cc(C)cc2OC)O)O)C
InChI InChI=1S/C24H27NO4/c1-12-8-17-16(6-7-18(26)22(17)20(9-12)28-4)23-19(27)11-15-10-13(2)25-14(3)21(15)24(23)29-5/h6-9,11,13-14,25-27H,10H2,1-5H3/t13-,14+/m0/s1
InChIKey RLVDDVWXQOZWDY-UONOGXRCSA-N
Formula C24H27NO4
HBA 5
HBD 3
MW 393.48
Rotatable Bonds 3
TPSA 70.95
LogP 4.84
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 393.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 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]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4

Level: 1

Mol. Weight: 393.48 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.17
Plasma Protein Binding
76.96
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
7.72
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.9
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.33
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.15
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
Safe
T. Pyriformis
-20.33
Rat (Acute)
2.34
Rat (Chronic Oral)
2.11
Fathead Minnow
4.99
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
471.23
Hydration Free Energy
-8.26
Log(D) at pH=7.4
4.37
Log(P)
4.3
Log S
-4.89
Log(Vapor Pressure)
-8.65
Melting Point
167.38
pKa Acid
9.52
pKa Basic
8.8
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 0.9508
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9265
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8959
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8905
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8864
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8816
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8649
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8565
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8551
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8541
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8512
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8449
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 4 0.8392
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.8366
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8359
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8246
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8195
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8194
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8189
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8122
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8112
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8063
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8028
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7920
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7888
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7881
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7826
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7806
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7797
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7781
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7771
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7762
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7761
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7759
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7696
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7630
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7616
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7590
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7542
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7531
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7524
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7511
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7468
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7429
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7392
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7378
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7368
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7358
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7325
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7306
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7293
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7291
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7290
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7290
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7274
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7256
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7248
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 3 0.7244
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7241
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7224
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7222
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7202
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7198
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7158
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7153
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7140
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 4 0.7134
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7130
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7128
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7112
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7103
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7102
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7090
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7069
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7062
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7062
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7060
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7050
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 4 0.7040
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7031
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7025
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7019

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