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Ealamine H

Family: Plantae - Ancistrocladaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid

Canonical Smiles	COc1c2c(C[C@@H](N([C@@H]2C)C)C)cc(c1c1ccc(c2c1cc(C)cc2O)OC)O
InChI	InChI=1S/C25H29NO4/c1-13-9-18-17(7-8-21(29-5)23(18)19(27)10-13)24-20(28)12-16-11-14(2)26(4)15(3)22(16)25(24)30-6/h7-10,12,14-15,27-28H,11H2,1-6H3/t14-,15+/m0/s1
InChIKey	UGEJDUMBFTVARC-LSDHHAIUSA-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 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]

Pubchem: 155527856

Chembl: CHEMBL4460670

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 407.51 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.99
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.9
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.97

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.14
Plasma Protein Binding: 75.56
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: 8.33
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.64
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.41
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.34
Micronucleos: Toxic
NR-AhR: Safe
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: -30.63
Rat (Acute): 2.4
Rat (Chronic Oral): 1.99
Fathead Minnow: 5.0
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: 472.89
Hydration Free Energy: -7.13
Log(D) at pH=7.4: 4.47
Log(P): 4.61
Log S: -4.9
Log(Vapor Pressure): -8.91
Melting Point: 147.55
pKa Acid: 9.32
pKa Basic: 8.54

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9216
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9106
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8964
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8818
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8790
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8758
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8684
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8492
Dihydrofolate reductase type 1 from Tn4003	P13955	DYRA_STAAU	Staphylococcus aureus	4	0.8352
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.8262
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8253
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8221
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8210
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8165
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.8107
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8105
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7979
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7962
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7960
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7796
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7721
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7711
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7615
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7600
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7574
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7549
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7536
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7529
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.7526
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7523
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7510
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7503
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7495
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7492
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7477
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7391
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7382
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7370
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7356
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7342
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7336
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7336
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7323
Calmodulin-domain protein kinase 1, putative	A3FQ16	A3FQ16_CRYPI	Cryptosporidium parvum	3	0.7284
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7271
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7260
Calmodulin-domain protein kinase 1, putative	A3FQ16	A3FQ16_CRYPI	Cryptosporidium parvum	4	0.7257
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7251
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7247
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7240
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7235
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7224
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7215
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7201
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7188
Ketimine reductase mu-crystallin	O54983	CRYM_MOUSE	Mus musculus	3	0.7175
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7162
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7107
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7100
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7099
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7083
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7032
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7020
Granule-bound starch synthase 1, chloroplastic/amyloplastic	Q0DEV5	SSG1_ORYSJ	Oryza sativa subsp. japonica	3	0.7012
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7004

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