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Pannorin

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Pyrone
- Subclass: Naphthopyrone

Canonical Smiles	Oc1cc(O)c2c(c1)cc(c1c2oc(=O)cc1O)C
InChI	InChI=1S/C14H10O5/c1-6-2-7-3-8(15)4-9(16)13(7)14-12(6)10(17)5-11(18)19-14/h2-5,15-17H,1H3
InChIKey	URYCWSZWYNTGEX-UHFFFAOYSA-N
Formula	C₁₄H₁₀O₅
HBA	5
HBD	3
MW	258.23
Rotatable Bonds	0
TPSA	90.9
LogP	2.37
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	19
Formal Charge	0
Fraction CSP3	0.07
Exact Mass	258.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus wentii	Trichocomaceae	Fungi	5066

Showing of synonyms

Form I.C, Bonus M, et al. (2019). Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg Med Chem,2019,27(20),115005. [View] [PubMed]

Pubchem: 54692973

Cas: 137023-81-5

Zinc: ZINC000006070476

Nmrshiftdb2: 70037617

Chembl: CHEMBL4576403

Comptox: DTXSID80160035

No compound-protein relationship available.

SMILES: O=c(o1)ccc(c1c23)ccc2cccc3

Level: 0

Mol. Weight: 258.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.81
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.57

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.33
Plasma Protein Binding: 76.29
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: 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: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 3.59
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.23
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.15
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.88
Micronucleos: Toxic
NR-AhR: Toxic
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: 4.73
Rat (Acute): 2.32
Rat (Chronic Oral): 2.85
Fathead Minnow: 4.15
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 452.76
Hydration Free Energy: -12.01
Log(D) at pH=7.4: 1.64
Log(P): 2.12
Log S: -3.93
Log(Vapor Pressure): -7.07
Melting Point: 298.2
pKa Acid: 7.62
pKa Basic: 5.49

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9193
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9166
Protoporphyrinogen oxidase, mitochondrial	O24164	PPOM_TOBAC	Nicotiana tabacum	3	0.9159
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9056
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8891
Bifunctional dihydrofolate reductase-thymidylate synthase	A7UD81	A7UD81_PLAFA	Plasmodium falciparum	4	0.8795
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8794
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8786
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	4	0.8715
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8653
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.8613
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.8604
Dicamba O-demethylase, oxygenase component	Q5S3I3	DDMC_STEMA	Stenotrophomonas maltophilia	3	0.8590
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8589
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8585
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8500
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8485
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8475
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8400
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8362
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8350
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	4	0.8328
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	4	0.8309
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8296
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8254
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8153
Bifunctional dihydrofolate reductase-thymidylate synthase	D9N170	D9N170_PLAFA	Plasmodium falciparum	4	0.8151
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8146
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.8139
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8134
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8107
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8055
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8048
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.8043
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8032
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7996
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7940
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7917
Alpha-1-acid glycoprotein 2	P19652	A1AG2_HUMAN	Homo sapiens	3	0.7910
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7852
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7816
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7805
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7804
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7717
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7700
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7686
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7677
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7676
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.7624
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7616
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7587
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7556
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7544
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7503
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7482
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27793	DRTS_TRYCR	Trypanosoma cruzi	3	0.7482
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7472
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7451
Bifunctional dihydrofolate reductase-thymidylate synthase	A7UD81	A7UD81_PLAFA	Plasmodium falciparum	3	0.7445
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7416
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7404
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7401
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7399
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7382
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7370
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7369
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.7355
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7348
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase	P12995	BIOA_ECOLI	Escherichia coli	3	0.7346
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7340
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7335
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7326
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7315
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7298
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7288
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7285
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7266
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7248
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7226
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7223
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.7219
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7217
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	4	0.7205
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7196
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.7165
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7160
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7153
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7147
Terminal oxygenase component of carbazole	Q84II6	Q84II6_JANS3	Janthinobacterium sp	3	0.7118
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7112
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7111
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7107
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7104
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7088
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7079
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7045
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7044
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7024
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7017
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7015
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7008
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7008
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7006

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