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Purealdin L

Family: Animalia - Aplysinellidae
Kingdom: Animalia
Class: Alkaloid
- Subclass: Bromotyrosine-Derived Alkaloid

Canonical Smiles	COC1=C(Br)[C@@H]([C@]2(C=C1Br)ON=C(C2)C(=O)NCCCCN=C(N)N)O
InChI	InChI=1S/C15H21Br2N5O4/c1-25-11-8(16)6-15(12(23)10(11)17)7-9(22-26-15)13(24)20-4-2-3-5-21-14(18)19/h6,12,23H,2-5,7H2,1H3,(H,20,24)(H4,18,19,21)/t12-,15+/m0/s1
InChIKey	VJEGSWJGTALRBW-SWLSCSKDSA-N
Formula	C₁₅H₂₁Br₂N₅O₄
HBA	6
HBD	4
MW	495.17
Rotatable Bonds	7
TPSA	144.55
LogP	0.58
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.53
Exact Mass	493.0
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Suberea mollis	Aplysinellidae	Animalia	1161115

Showing of synonyms

Shaala LA, Bamane FH, et al. (2011). Brominated arginine-derived alkaloids from the Red Sea sponge Suberea mollis. Journal of Natural Products,2011,74(6),1517-1520. [View] [PubMed]

Pubchem: 10391052

Gnps: CCMSLIB00010012976

Zinc: ZINC000038749709

Chebi: 69839

Nmrshiftdb2: 60146364

Metabolights: MTBLC69839

Chembl: CHEMBL550970

No compound-protein relationship available.

SMILES: O1N=CCC12C=CC=CC2

Level: 0

Mol. Weight: 495.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.3
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.080
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.74

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.370
Plasma Protein Binding: 32.3
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 5.550
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.440
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.180
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 10.490
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: -2.610
Rat (Acute): 2.430
Rat (Chronic Oral): 1.570
Fathead Minnow: 4.280
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 456.910
Hydration Free Energy: -12.030
Log(D) at pH=7.4: 0.840
Log(P): -0.2
Log S: -1.48
Log(Vapor Pressure): -10.86
Melting Point: 177.8
pKa Acid: 7.46
pKa Basic: 7.21

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.9725
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.9725
Triosephosphate isomerase	P00942	TPIS_YEAST	Saccharomyces cerevisiae	3	0.9441
Triosephosphate isomerase	P00942	TPIS_YEAST	Saccharomyces cerevisiae	3	0.9441
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9236
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9236
NAD-dependent protein deacetylase sirtuin-3, mitochondrial	Q9NTG7	SIR3_HUMAN	Homo sapiens	3	0.9084
NAD-dependent protein deacetylase sirtuin-3, mitochondrial	Q9NTG7	SIR3_HUMAN	Homo sapiens	3	0.9084
Shikimate kinase	P9WPY3	AROK_MYCTU	Mycobacterium tuberculosis	3	0.8914
Shikimate kinase	P9WPY3	AROK_MYCTU	Mycobacterium tuberculosis	3	0.8914
Mevalonate kinase	Q4Q6K7	Q4Q6K7_LEIMA	Leishmania major	3	0.8873
Mevalonate kinase	Q4Q6K7	Q4Q6K7_LEIMA	Leishmania major	3	0.8873
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.8201
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.8201
Enterochelin uptake periplasmic binding protein	Q0P8Q4	Q0P8Q4_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	3	0.8032
Enterochelin uptake periplasmic binding protein	Q0P8Q4	Q0P8Q4_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	3	0.8032
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8007
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8007
Integrin alpha-5	P08648	ITA5_HUMAN	Homo sapiens	3	0.7939
Integrin alpha-5	P08648	ITA5_HUMAN	Homo sapiens	3	0.7939
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	4	0.7893
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	4	0.7893
Regucalcin	Q64374	RGN_MOUSE	Mus musculus	3	0.7823
Regucalcin	Q64374	RGN_MOUSE	Mus musculus	3	0.7823
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7768
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7768
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.7719
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.7719
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7716
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7716
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	4	0.7689
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	4	0.7689
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	3	0.7384
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	3	0.7384
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7357
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7357
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7356
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7356
Xylose isomerase	P12070	XYLA_ARTS7	Arthrobacter sp	3	0.7334
Xylose isomerase	P12070	XYLA_ARTS7	Arthrobacter sp	3	0.7334
Mexicain	P84346	MEX1_JACME	Jacaratia mexicana	3	0.7122
Mexicain	P84346	MEX1_JACME	Jacaratia mexicana	3	0.7122
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	3	0.7073
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	3	0.7073

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