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Jozilebomine A

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

Canonical Smiles	COc1cccc2c1c(O)c(c1ccc3c(c1O)c(OC)cc(c3c1ccc3c(c1O)[C@@H](C)N[C@@H](C3)C)C)c(c2c1ccc2c(c1O)[C@@H](C)N[C@@H](C2)C)C
InChI	InChI=1S/C46H48N2O6/c1-21-18-35(54-8)42-30(36(21)31-14-12-27-19-22(2)47-25(5)39(27)43(31)49)16-17-33(45(42)51)38-24(4)37(29-10-9-11-34(53-7)41(29)46(38)52)32-15-13-28-20-23(3)48-26(6)40(28)44(32)50/h9-18,22-23,25-26,47-52H,19-20H2,1-8H3/t22-,23-,25-,26-/m1/s1
InChIKey	MPLPBURRFZLQFR-OQUNMALSSA-N
Formula	C₄₆H₄₈N₂O₆
HBA	8
HBD	6
MW	724.9
Rotatable Bonds	5
TPSA	123.44
LogP	9.64
Number Rings	8
Number Aromatic Rings	6
Heavy Atom Count	54
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	724.35
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus ileboensis	Ancistrocladaceae	Plantae	1367080

Showing of synonyms

Li J, Seupel R, et al. (2017). Jozilebomines A and B, Naphthylisoquinoline Dimers from the Congolese Liana Ancistrocladus ileboensis, with Antiausterity Activities against the PANC-1 Human Pancreatic Cancer Cell Line.. Journal of natural products,2017, 80(10), 2807-2817. [View] [PubMed]

Pubchem: 145953130

Chembl: CHEMBL4166452

No compound-protein relationship available.

SMILES: C1NCCc(c12)ccc(c2)-c3cc(cc(c34)cccc4)-c(cc5)cc(c56)cccc6-c(c7)ccc(c78)CCNC8

Level: 3

Mol. Weight: 724.9 g/mol

SMILES: c1cccc(c12)ccc(c2)-c(cc3)cc(c34)cccc4-c(c5)ccc(c56)CCNC6

Level: 2

Mol. Weight: 724.9 g/mol

SMILES: c1cccc(c12)ccc(c2)-c(cc(c34)cccc4)cc3-c(c5)ccc(c56)CCNC6

Level: 2

Mol. Weight: 724.9 g/mol

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

Level: 1

Mol. Weight: 724.9 g/mol

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

Level: 1

Mol. Weight: 724.9 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 724.9 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 724.9 g/mol

Antimalarial

Absorption

Caco-2 (logPapp): -5.75
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 19.130
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 3255.89

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.450
Plasma Protein Binding: 88.78
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 6.530
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -77.160
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.780
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.570
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -5903011.270
Rat (Acute): 2.250
Rat (Chronic Oral): 2.200
Fathead Minnow: 7456.370
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: 658876.900
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 5.290
Log(P): 7.34
Log S: -7.2
Log(Vapor Pressure): -21658.44
Melting Point: 264.01
pKa Acid: -130.44
pKa Basic: 10.69

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	0.9449
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9171
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9007
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8659
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.8381
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.8373
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8289
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8212
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.8181
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7941
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7923
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7666
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7572
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7552
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7475
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7407
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7321
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7306
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7248
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.7212
Dihydrofolate reductase	P9WNX1	DYR_MYCTU	Mycobacterium tuberculosis	3	0.7160
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7144
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	3	0.7025
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7010
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7000

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