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Fonsecin B

Family: Fungi - Dematiaceae
Kingdom: Fungi
Class: Lactone
- Subclass: Pyrone Derivative

Canonical Smiles	COc1cc2cc3OC(C)(O)CC(=O)c3c(c2c(c1)OC)O
InChI	InChI=1S/C16H16O6/c1-16(19)7-10(17)14-12(22-16)5-8-4-9(20-2)6-11(21-3)13(8)15(14)18/h4-6,18-19H,7H2,1-3H3
InChIKey	ZYTKFYQKQVYVMW-UHFFFAOYSA-N
Formula	C₁₆H₁₆O₆
HBA	6
HBD	2
MW	304.3
Rotatable Bonds	2
TPSA	85.22
LogP	2.24
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.31
Exact Mass	304.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Alternaria alternata	Dematiaceae	Fungi	5599

Showing of synonyms

Shaaban M, Shaaban KA, et al. (2012). Seven naphtho-gamma-pyrones from the marine derived fungus Alternaria alternata: structure elucidation and biological properties. Organic and Medicinal Chemistry Letters,2012,2,6. [View] [PubMed]

Pubchem: 160596

Cas: 1856-95-7

Chebi: 133825

Nmrshiftdb2: 70014561

Metabolights: MTBLC133825

CPRiL: 258353

SMILES: O=C1CCOc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 304.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.56
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.680
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.93

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.070
Plasma Protein Binding: 46.97
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: 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: Non-Inhibitor

Excretion

Clearance: 5.730
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.290
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.770
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.580
Micronucleos: Toxic
NR-AhR: Toxic
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: 3.780
Rat (Acute): 2.400
Rat (Chronic Oral): 2.450
Fathead Minnow: 4.420
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 402.470
Hydration Free Energy: -10.430
Log(D) at pH=7.4: 2.300
Log(P): 3.07
Log S: -4.39
Log(Vapor Pressure): -6.68
Melting Point: 158.81
pKa Acid: 7.22
pKa Basic: 3.47

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9698
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9698
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9279
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9279
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9182
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9182
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9153
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9153
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9123
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9123
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.9058
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.9058
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8823
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8823
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.8777
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.8777
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8766
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8766
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8696
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8696
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8645
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8645
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8618
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8618
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.8617
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.8617
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8507
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8507
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8452
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8452
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8386
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8386
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8349
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8349
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.8151
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.8151
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8137
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8137
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8129
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8129
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8066
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8066
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7828
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7828
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7826
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7826
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7814
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7814
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7790
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7790
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7723
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7723
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7648
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7648
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7635
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7635
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7623
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7623
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7554
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7554
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7530
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7530
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7521
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7521
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7481
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7481
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7455
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7455
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7326
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7326
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7318
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7318
Protein mono-ADP-ribosyltransferase PARP14	Q460N5	PAR14_HUMAN	Homo sapiens	3	0.7310
Protein mono-ADP-ribosyltransferase PARP14	Q460N5	PAR14_HUMAN	Homo sapiens	3	0.7310
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7293
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7293
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7249
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7249
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7223
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7223
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7217
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7217
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7213
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7213
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7210
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7210
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7199
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7199
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7196
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7196
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7184
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7184
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7163
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7163
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7160
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7160
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7132
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7132
D-mycarose 3-C-methyltransferase	Q194Q4	Q194Q4_STRAA	Streptomyces argillaceus	4	0.7124
D-mycarose 3-C-methyltransferase	Q194Q4	Q194Q4_STRAA	Streptomyces argillaceus	4	0.7124
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7113
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7113
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7098
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7098
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7068
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7068
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7065
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7065
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7063
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7063
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7052
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7052
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7044
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7044
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	3	0.7041
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	3	0.7041
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7039
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7039
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	4	0.7036
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	4	0.7036
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7017
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7017
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7008
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7008

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