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Asperpyrone

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Lignan

Canonical Smiles	OC(=O)c1cc(C)c(=O)oc1c1cccc(c1C(=O)O)O
InChI	InChI=1S/C14H10O7/c1-6-5-8(12(16)17)11(21-14(6)20)7-3-2-4-9(15)10(7)13(18)19/h2-5,15H,1H3,(H,16,17)(H,18,19)
InChIKey	BRURYVZJSBEMPL-UHFFFAOYSA-N
Formula	C₁₄H₁₀O₇
HBA	5
HBD	3
MW	290.23
Rotatable Bonds	3
TPSA	125.04
LogP	1.72
Number Rings	2
Number Aromatic Rings	2
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.07
Exact Mass	290.04
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus sp.	Trichocomaceae	Fungi	—

Showing of synonyms

Jouda JB, Njoya EM, et al. (2023). Asperpyrone, a rare α-pyrone metabolite produced by an endophytic fungus Aspergillus sp. isolated from Garicinia smeathmannii (Planch. & Triana) Oliv.. Natural product research,2023, 37(1), 8-15. [View] [PubMed]

CPRiL: 173250

SMILES: c1ccccc1-c2cccc(=O)o2

Level: 1

Mol. Weight: 290.23 g/mol

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 290.23 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 290.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.75
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.81
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.13

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.92
Plasma Protein Binding: 54.31
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: Non-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: 3.54
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.01
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 2.06
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.02
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: 2.35
Rat (Acute): 2.17
Rat (Chronic Oral): 3.69
Fathead Minnow: 3.69
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 460.0
Hydration Free Energy: -6.69
Log(D) at pH=7.4: -1.07
Log(P): 2.78
Log S: -3.02
Log(Vapor Pressure): -9.42
Melting Point: 287.27
pKa Acid: 4.64
pKa Basic: 6.41

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	3	0.8731
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8715
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	4	0.8435
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8408
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8341
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.8322
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8281
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8281
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8129
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8092
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8025
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7897
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7844
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	3	0.7782
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7755
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7739
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7601
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	3	0.7563
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7502
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7496
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7463
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7457
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7384
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7379
Enoyl-acyl carrier protein reductase	Q6TEI5	Q6TEI5_PLABE	Plasmodium berghei	4	0.7329
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7325
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7325
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7267
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7265
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7264
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	4	0.7259
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7249
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7214
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7180
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7162
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7134
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7121
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7068
Cytosol aminopeptidase	P00727	AMPL_BOVIN	Bos taurus	2	0.7058
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7055
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	3	0.7038
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7022
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7016

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