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Michellamine A2

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

Canonical Smiles	COc1cc(C)cc2c1c(O)c(cc2c1c(O)cc(c2c1C[C@@H](C)N[C@@H]2C)O)c1cc(c2c(O)cc(c3c2C[C@@H](C)N[C@H]3C)O)c2c(c1O)c(OC)cc(c2)C
InChI	InChI=1S/C46H48N2O8/c1-19-9-25-27(41-31-13-21(3)47-23(5)39(31)33(49)17-35(41)51)15-29(45(53)43(25)37(11-19)55-7)30-16-28(26-10-20(2)12-38(56-8)44(26)46(30)54)42-32-14-22(4)48-24(6)40(32)34(50)18-36(42)52/h9-12,15-18,21-24,47-54H,13-14H2,1-8H3/t21-,22-,23-,24+/m1/s1
InChIKey	GMLBVLXDRNJFGR-YCAMKHIRSA-N
Formula	C₄₆H₄₈N₂O₈
HBA	10
HBD	8
MW	756.9
Rotatable Bonds	5
TPSA	163.9
LogP	9.05
Number Rings	8
Number Aromatic Rings	6
Heavy Atom Count	56
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	756.34
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus likoko	Ancistrocladaceae	Plantae	714102

Showing of synonyms

Fayez S, Feineis D, et al. (2017). Ancistrolikokines E-H and related 5,8'-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko with antiausterity activities against PANC-1 human pancreatic cancer cells.. RSC Adv., 2017,7, 53740-53751. [View]

Pubchem: 129907404

No compound-protein relationship available.

SMILES: C1CNCc(c12)cccc2-c3cc(cc(c34)cccc4)-c(cc(c56)cccc6)cc5-c7cccc(c78)CNCC8

Level: 3

Mol. Weight: 756.9 g/mol

SMILES: c1cccc(c12)ccc(c2)-c(cc(c34)cccc4)cc3-c5cccc(c56)CNCC6

Level: 2

Mol. Weight: 756.9 g/mol

SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4

Level: 1

Mol. Weight: 756.9 g/mol

SMILES: c1cccc(c12)ccc(c2)-c(c3)ccc(c34)cccc4

Level: 1

Mol. Weight: 756.9 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 756.9 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 756.9 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.91
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 40.500
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 6115.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.210
Plasma Protein Binding: 84.07
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 7.380
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -145.090
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.640
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.240
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -11092655.960
Rat (Acute): 1.970
Rat (Chronic Oral): 2.790
Fathead Minnow: 14007.510
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 1241768.150
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 4.930
Log(P): 7.37
Log S: -6.93
Log(Vapor Pressure): -40845.29
Melting Point: 309.51
pKa Acid: -264.37
pKa Basic: 10.67

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9144
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9144
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9111
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9111
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8971
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8971
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8486
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8486
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8289
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8289
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7639
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7639
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7619
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7619
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7422
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7422
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7415
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7415
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7375
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7375
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7325
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7325
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27552	Q27552_CRYPV	Cryptosporidium parvum	3	0.7282
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27552	Q27552_CRYPV	Cryptosporidium parvum	3	0.7282
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7275
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7275
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7251
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7251
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7197
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7197
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7075
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7075
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7050
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7050
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7037
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7037
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7036
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7036

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