ANPDB

Select a section from the left sidebar

Aerothionin

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)NCCCCNC(=O)C1=NO[C@@]2(C1)C=C(Br)C(=C([C@@H]2O)Br)OC)O
InChI	InChI=1S/C24H26Br4N4O8/c1-37-17-11(25)7-23(19(33)15(17)27)9-13(31-39-23)21(35)29-5-3-4-6-30-22(36)14-10-24(40-32-14)8-12(26)18(38-2)16(28)20(24)34/h7-8,19-20,33-34H,3-6,9-10H2,1-2H3,(H,29,35)(H,30,36)/t19-,20-,23+,24+/m0/s1
InChIKey	BJWQSQOWGBUSFC-UWXQAFAOSA-N
Formula	C₂₄H₂₆Br₄N₄O₈
HBA	10
HBD	4
MW	818.11
Rotatable Bonds	9
TPSA	160.3
LogP	2.84
Number Rings	4
Number Aromatic Rings	0
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	813.85
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: 301120

Cas: 28714-26-3

Gnps: CCMSLIB00010012970

Nmrshiftdb2: 70129976

Chembl: CHEMBL1999742

CPRiL: 229765

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

Level: 1

Mol. Weight: 818.11 g/mol

SMILES: O1N=CCC12C=CC=CC2

Level: 0

Mol. Weight: 818.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.27
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.120
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.15

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.990
Plasma Protein Binding: 74.43
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 2.560
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.880
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.410
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 8.680
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: Safe
T. Pyriformis: -3774.370
Rat (Acute): 2.510
Rat (Chronic Oral): 1.650
Fathead Minnow: 15.890
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: 523.140
Hydration Free Energy: -2.900
Log(D) at pH=7.4: 3.490
Log(P): 3.33
Log S: -3.99
Log(Vapor Pressure): -10.35
Melting Point: 243.5
pKa Acid: 6.81
pKa Basic: 3.31

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	0.9722
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.9722
Triosephosphate isomerase	P00942	TPIS_YEAST	Saccharomyces cerevisiae	3	0.9447
Triosephosphate isomerase	P00942	TPIS_YEAST	Saccharomyces cerevisiae	3	0.9447
Shikimate kinase	P9WPY3	AROK_MYCTU	Mycobacterium tuberculosis	3	0.9000
Shikimate kinase	P9WPY3	AROK_MYCTU	Mycobacterium tuberculosis	3	0.9000
Regucalcin	Q64374	RGN_MOUSE	Mus musculus	3	0.8966
Regucalcin	Q64374	RGN_MOUSE	Mus musculus	3	0.8966
Mevalonate kinase	Q4Q6K7	Q4Q6K7_LEIMA	Leishmania major	3	0.8937
Mevalonate kinase	Q4Q6K7	Q4Q6K7_LEIMA	Leishmania major	3	0.8937
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8812
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8812
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.8243
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.8243
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7969
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7969
Enterochelin uptake periplasmic binding protein	Q0P8Q4	Q0P8Q4_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	3	0.7969
Enterochelin uptake periplasmic binding protein	Q0P8Q4	Q0P8Q4_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	3	0.7969
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.7770
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.7770
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7767
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7767
Fatty acid-binding protein 2, liver	P81400	FABP2_AMBME	Ambystoma mexicanum	3	0.7624
Fatty acid-binding protein 2, liver	P81400	FABP2_AMBME	Ambystoma mexicanum	3	0.7624
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7493
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7493
Xylose isomerase	P12070	XYLA_ARTS7	Arthrobacter sp	3	0.7486
Xylose isomerase	P12070	XYLA_ARTS7	Arthrobacter sp	3	0.7486
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7348
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7348
Mexicain	P84346	MEX1_JACME	Jacaratia mexicana	3	0.7235
Mexicain	P84346	MEX1_JACME	Jacaratia mexicana	3	0.7235
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7183
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7183
nebramycin 5' synthase	Q70IY1	TOBZ_STRSD	Streptoalloteichus tenebrarius	3	0.7156
nebramycin 5' synthase	Q70IY1	TOBZ_STRSD	Streptoalloteichus tenebrarius	3	0.7156
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	3	0.7112
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	3	0.7112

Download SDF