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Ealamine A

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

Canonical Smiles	COc1c2[C@@H](C)N[C@H](Cc2cc(c1c1ccc(c2c1cc(C)cc2OC)OC)O)C
InChI	InChI=1S/C25H29NO4/c1-13-9-18-17(7-8-20(28-4)24(18)21(10-13)29-5)23-19(27)12-16-11-14(2)26-15(3)22(16)25(23)30-6/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15+/m0/s1
InChIKey	CGBBXIBLWODGSI-LSDHHAIUSA-N
Formula	C₂₅H₂₉NO₄
HBA	5
HBD	2
MW	407.51
Rotatable Bonds	4
TPSA	59.95
LogP	5.14
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]

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 259.35 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 133.19 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 128.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.04
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.87
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.61

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.29
Plasma Protein Binding: 76.69
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: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.58
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.01
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.2
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.75
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: -33.44
Rat (Acute): 2.54
Rat (Chronic Oral): 2.04
Fathead Minnow: 5.35
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: 468.52
Hydration Free Energy: -6.04
Log(D) at pH=7.4: 4.35
Log(P): 4.51
Log S: -4.8
Log(Vapor Pressure): -8.73
Melting Point: 161.33
pKa Acid: 10.27
pKa Basic: 9.44

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	0.9371
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9098
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8992
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8587
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8499
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8497
Dihydrofolate reductase type 1 from Tn4003	P13955	DYRA_STAAU	Staphylococcus aureus	4	0.8425
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8379
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8328
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.8301
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8298
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8278
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8214
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.8197
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8050
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.8035
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8010
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8007
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7997
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7989
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7981
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7941
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7940
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7891
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7875
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7814
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7810
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7782
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7770
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7764
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7635
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7592
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7575
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7545
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7486
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7481
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7475
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7468
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7463
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7455
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7433
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7411
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7405
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7358
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7351
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7318
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7311
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7286
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7235
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7216
Ketimine reductase mu-crystallin	O54983	CRYM_MOUSE	Mus musculus	3	0.7194
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7185
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7180
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7161
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7158
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7119
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7091
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7082
Calmodulin-domain protein kinase 1, putative	A3FQ16	A3FQ16_CRYPI	Cryptosporidium parvum	4	0.7067
Granule-bound starch synthase 1, chloroplastic/amyloplastic	Q0DEV5	SSG1_ORYSJ	Oryza sativa subsp. japonica	3	0.7066
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7031
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7019
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7013
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7004
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7002

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