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Homoaerothionin

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)NCCCCCNC(=O)C1=NO[C@@]2(C1)C=C(Br)C(=C([C@@H]2O)Br)OC)O
InChI	InChI=1S/C25H28Br4N4O8/c1-38-18-12(26)8-24(20(34)16(18)28)10-14(32-40-24)22(36)30-6-4-3-5-7-31-23(37)15-11-25(41-33-15)9-13(27)19(39-2)17(29)21(25)35/h8-9,20-21,34-35H,3-7,10-11H2,1-2H3,(H,30,36)(H,31,37)/t20-,21-,24+,25+/m0/s1
InChIKey	UXPNMQCEVMBCIR-KXTAGPOFSA-N
Formula	C₂₅H₂₈Br₄N₄O₈
HBA	10
HBD	4
MW	832.14
Rotatable Bonds	10
TPSA	160.3
LogP	3.23
Number Rings	4
Number Aromatic Rings	0
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.52
Exact Mass	827.86
Number of Lipinski Rule Violations	1

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

Showing of synonyms

Abou-Shoer MI, Shaala LA, et al. (2008). Bioactive brominated metabolites from the red sea sponge Suberea mollis. Journal of Natural Products,2008,71(8),1464-1467. [View] [PubMed]

Pubchem: 100315

Gnps: CCMSLIB00010011957

Zinc: ZINC000150564561

Nmrshiftdb2: 60146231

Chembl: CHEMBL229679

CPRiL: 422347

SMILES: C1C=CC=CC12CC(=NO2)C(=O)NCCCCCNC(=O)C(=NO3)CC34C=CC=CC4

Level: 1

Mol. Weight: 832.14 g/mol

SMILES: O1N=CCC12C=CC=CC2

Level: 0

Mol. Weight: 832.14 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.24
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.090
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.44

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.040
Plasma Protein Binding: 75.08
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: Inhibitor
CYP 2C9 Substrate: Non-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: 3.110
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.930
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.390
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 8.670
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -6141.440
Rat (Acute): 2.500
Rat (Chronic Oral): 1.740
Fathead Minnow: 20.280
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 478.660
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 3.770
Log(P): 3.61
Log S: -4.19
Log(Vapor Pressure): -10.17
Melting Point: 236.61
pKa Acid: 6.94
pKa Basic: 3.85

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	0.9749
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.9749
Triosephosphate isomerase	P00942	TPIS_YEAST	Saccharomyces cerevisiae	3	0.9449
Triosephosphate isomerase	P00942	TPIS_YEAST	Saccharomyces cerevisiae	3	0.9449
1,4-alpha-glucan branching enzyme GlgB	A7ZSW5	GLGB_ECO24	Escherichia coli O139:H28	3	0.9060
1,4-alpha-glucan branching enzyme GlgB	A7ZSW5	GLGB_ECO24	Escherichia coli O139:H28	3	0.9060
Mevalonate kinase	Q4Q6K7	Q4Q6K7_LEIMA	Leishmania major	3	0.8977
Mevalonate kinase	Q4Q6K7	Q4Q6K7_LEIMA	Leishmania major	3	0.8977
Shikimate kinase	P9WPY3	AROK_MYCTU	Mycobacterium tuberculosis	3	0.8946
Shikimate kinase	P9WPY3	AROK_MYCTU	Mycobacterium tuberculosis	3	0.8946
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.8245
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.8245
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8236
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8236
Enterochelin uptake periplasmic binding protein	Q0P8Q4	Q0P8Q4_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	3	0.8088
Enterochelin uptake periplasmic binding protein	Q0P8Q4	Q0P8Q4_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	3	0.8088
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.7828
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.7828
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7617
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7617
Xylose isomerase	P12070	XYLA_ARTS7	Arthrobacter sp	3	0.7609
Xylose isomerase	P12070	XYLA_ARTS7	Arthrobacter sp	3	0.7609
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7332
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7332
Fluoroacetyl-CoA thioesterase	Q1EMV2	FLK_STRCT	Streptantibioticus cattleyicolor	3	0.7301
Fluoroacetyl-CoA thioesterase	Q1EMV2	FLK_STRCT	Streptantibioticus cattleyicolor	3	0.7301
Mexicain	P84346	MEX1_JACME	Jacaratia mexicana	3	0.7210
Mexicain	P84346	MEX1_JACME	Jacaratia mexicana	3	0.7210
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7188
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7188
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	3	0.7121
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	3	0.7121
Cytidine deaminase	P19079	CDD_BACSU	Bacillus subtilis	3	0.7034
Cytidine deaminase	P19079	CDD_BACSU	Bacillus subtilis	3	0.7034

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