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Allantopyrone E

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Pyrone

Canonical Smiles	C/C=C/C=C\C(=O)OCc1c(=O)oc(c(c1OC)CO)/C=C/CO
InChI	InChI=1S/C17H20O7/c1-3-4-5-8-15(20)23-11-13-16(22-2)12(10-19)14(7-6-9-18)24-17(13)21/h3-8,18-19H,9-11H2,1-2H3/b4-3+,7-6+,8-5-
InChIKey	UOMAGVHZSLPVJJ-RLBCQOATSA-N
Formula	C₁₇H₂₀O₇
HBA	7
HBD	2
MW	336.34
Rotatable Bonds	8
TPSA	106.2
LogP	1.32
Number Rings	1
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	336.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus versicolor	Trichocomaceae	Fungi	46472

Showing of synonyms

Elsbaey M, Tanaka C, et al. (2022). Allantopyrone E, a rare α-pyrone metabolite from the mangrove derived fungus Aspergillus versicolor. Nat Prod Res,2022,36(3),760-764. [View]

Pubchem: 46704283

Zinc: ZINC000138298548

Nmrshiftdb2: 70078040

CPRiL: 154961

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 336.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.03
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.25
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.79

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.61
Plasma Protein Binding: 20.08
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-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: 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: 1.44
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.46
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.77
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.45
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: 1.24
Rat (Acute): 2.04
Rat (Chronic Oral): 2.69
Fathead Minnow: 4.67
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 416.43
Hydration Free Energy: -10.72
Log(D) at pH=7.4: 0.89
Log(P): 0.79
Log S: -3.11
Log(Vapor Pressure): -7.42
Melting Point: 88.77
pKa Acid: 8.39
pKa Basic: 4.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9443
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9336
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9207
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9183
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.9161
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.9054
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8943
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8896
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8872
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8859
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8828
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8794
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8754
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8743
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8666
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8660
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8642
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8618
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8602
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.8547
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.8492
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8419
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8416
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8409
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8336
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8307
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8255
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8251
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.8242
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8238
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8233
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8223
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8196
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8193
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8138
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8128
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8126
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8115
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8069
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8066
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8042
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8019
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7965
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7946
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7907
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7865
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7841
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7783
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7719
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7707
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7687
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7652
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7650
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7645
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7628
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7573
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7558
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7549
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7511
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic	P49235	HGGL1_MAIZE	Zea mays	3	0.7490
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7481
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7481
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7469
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7457
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7436
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7430
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7429
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7411
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7385
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7383
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7383
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7368
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7352
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7337
SRSF protein kinase 1	Q96SB4	SRPK1_HUMAN	Homo sapiens	3	0.7331
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7329
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7288
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7276
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7270
L-methionine gamma-lyase	Q84AR1	Q84AR1_CITFR	Citrobacter freundii	3	0.7254
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7243
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7237
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7236
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	3	0.7233
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7219
Tyrosine 3-monooxygenase	P04177	TY3H_RAT	Rattus norvegicus	3	0.7210
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7208
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7202
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7198
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7191
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7185
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7163
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7150
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7149
Benzoylformate decarboxylase	P20906	MDLC_PSEPU	Pseudomonas putida	3	0.7133
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	2	0.7127
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7126
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7122
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7120
Metallophosphoesterase	A3DJ38	A3DJ38_HUNT2	Clostridium thermocellum	2	0.7115
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7112
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7111
GMP reductase	Q81JJ9	GUAC_BACAN	Bacillus anthracis	2	0.7111
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7094
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7085
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7085
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7070
Ribonucleoside-diphosphate reductase 2 subunit alpha	Q08698	RIR3_SALTY	Salmonella typhimurium	2	0.7065
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7061
orotidine-5'-phosphate decarboxylase	Q8T6J6	Q8T6J6_PLAFA	Plasmodium falciparum	4	0.7059
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7052
chitinase	B0Y2Y2	B0Y2Y2_ASPFC	Aspergillus fumigatus	3	0.7043
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7041
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7037
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7026
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7020
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7012

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