Ealamine F - Compound Card

Ealamine F

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Ealamine F

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc2C[C@H](C)N[C@@H](c2c(c1c1ccc(c2c1cc(C)cc2OC)OC)OC)C
InChI InChI=1S/C26H31NO4/c1-14-10-19-18(8-9-20(28-4)24(19)21(11-14)29-5)25-22(30-6)13-17-12-15(2)27-16(3)23(17)26(25)31-7/h8-11,13,15-16,27H,12H2,1-7H3/t15-,16+/m0/s1
InChIKey MWONATDKBORUOS-JKSUJKDBSA-N
Formula C26H31NO4
HBA 5
HBD 1
MW 421.54
Rotatable Bonds 5
TPSA 48.95
LogP 5.44
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 421.23
Number of Lipinski Rule Violations 1
# 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: 421.54 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.2
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.260
Plasma Protein Binding
72.98
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.360
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.020
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.080
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
10.220
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
-56.360
Rat (Acute)
2.910
Rat (Chronic Oral)
2.010
Fathead Minnow
5.790
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
469.280
Hydration Free Energy
-4.550
Log(D) at pH=7.4
4.110
Log(P)
4.91
Log S
-4.47
Log(Vapor Pressure)
-8.45
Melting Point
146.16
pKa Acid
12.36
pKa Basic
10.18
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 0.9544
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9269
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9080
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8980
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8898
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8885
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8678
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8588
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8400
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8355
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8343
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.8287
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8202
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8170
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8145
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8126
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8110
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8080
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8070
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7981
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7964
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7906
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7878
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7855
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7852
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7783
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7693
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7688
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7630
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7622
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7595
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7594
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7590
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7549
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7538
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7526
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7524
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7492
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7461
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7445
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7423
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7415
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7412
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7408
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7364
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7348
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7346
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7340
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7339
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7336
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7335
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7285
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7278
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7259
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7245
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7245
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7237
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7237
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7228
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7225
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7222
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7211
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7184
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 3 0.7170
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7169
Granule-bound starch synthase 1, chloroplastic/amyloplastic Q0DEV5 SSG1_ORYSJ Oryza sativa subsp. japonica 3 0.7164
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.7161
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7154
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7137
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7131
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7123
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7117
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7070
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7062
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7054
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7026
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7001

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