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Yaoundamine A

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

Canonical Smiles	COc1c2C(=N[C@@H](Cc2cc(c1c1ccc(c2c1cc(C)cc2OC)O)O)C)C
InChI	InChI=1S/C24H25NO4/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/h6-9,11,13,26-27H,10H2,1-5H3/t13-/m1/s1
InChIKey	YNZRHQDRHHJZQU-CYBMUJFWSA-N
Formula	C₂₄H₂₅NO₄
HBA	5
HBD	2
MW	391.47
Rotatable Bonds	3
TPSA	71.28
LogP	5.0
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	391.18
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]

Pubchem: 392429

Zinc: ZINC000005849017

Nmrshiftdb2: 70104637

Chembl: CHEMBL4451177

No compound-protein relationship available.

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCN=C4

Level: 1

Mol. Weight: 391.47 g/mol

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 391.47 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 391.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.85
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.78
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.55

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.4
Plasma Protein Binding: 87.93
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 5.22
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.63
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.45
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.96
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: -14.13
Rat (Acute): 2.31
Rat (Chronic Oral): 2.52
Fathead Minnow: 5.2
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: 483.65
Hydration Free Energy: -6.71
Log(D) at pH=7.4: 3.86
Log(P): 5.23
Log S: -6.35
Log(Vapor Pressure): -8.2
Melting Point: 185.94
pKa Acid: 9.27
pKa Basic: 7.7

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.9483
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9165
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9140
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8868
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8739
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8721
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8682
Dihydrofolate reductase type 1 from Tn4003	P13955	DYRA_STAAU	Staphylococcus aureus	4	0.8681
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8593
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.8518
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8517
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8491
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8415
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.8373
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8339
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8266
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8253
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8225
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.8214
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.8149
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8130
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8109
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8027
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7942
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7901
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.7865
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7837
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.7816
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7782
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7771
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7766
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7737
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7720
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7575
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7573
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	4	0.7534
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7528
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7516
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7472
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7457
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7421
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7395
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7393
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7375
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7355
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7348
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7339
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7330
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7323
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7300
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7296
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7283
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7276
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7257
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7247
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7216
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7214
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7185
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7170
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7155
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7135
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7126
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7108
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7106
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7094
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7090
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7086
Calmodulin-domain protein kinase 1, putative	A3FQ16	A3FQ16_CRYPI	Cryptosporidium parvum	4	0.7073
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7045
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7044
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7042
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7042
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7040
Granule-bound starch synthase 1, chloroplastic/amyloplastic	Q0DEV5	SSG1_ORYSJ	Oryza sativa subsp. japonica	3	0.7034
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7032

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