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Butyrolactone I

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Lactone
- Subclass: Butyrolactone Derivative

Canonical Smiles	COC(=O)[C@@]1(Cc2ccc(c(c2)CC=C(C)C)O)OC(=O)C(=C1c1ccc(cc1)O)O
InChI	InChI=1S/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-24(23(29)30-3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m0/s1
InChIKey	NGOLMNWQNHWEKU-DEOSSOPVSA-N
Formula	C₂₄H₂₄O₇
HBA	7
HBD	3
MW	424.45
Rotatable Bonds	6
TPSA	113.29
LogP	3.59
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	424.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus flavipes	Trichocomaceae	Fungi	41900

Showing of synonyms

Nagia MM, El-Metwally MM, et al. (2012). Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Organic and Medicinal Chemistry Letters,2012,2(1),9. [View] [PubMed]

Pubchem: 51340302

Gnps: CCMSLIB00004694976

Zinc: ZINC000027415684

Chebi: 191397

Nmrshiftdb2: 80003138

Chembl: CHEMBL1242973

CPRiL: 101537

SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3

Level: 2

Mol. Weight: 424.45 g/mol

SMILES: O=C1C=CC(O1)Cc2ccccc2

Level: 1

Mol. Weight: 424.45 g/mol

SMILES: C1OC(=O)C=C1c2ccccc2

Level: 1

Mol. Weight: 424.45 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 424.45 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 424.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.22
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.840
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.54

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.030
Plasma Protein Binding: 63.85
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.620
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.200
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.510
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.590
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: -34.070
Rat (Acute): 2.220
Rat (Chronic Oral): 2.960
Fathead Minnow: 5.120
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 480.380
Hydration Free Energy: -3.630
Log(D) at pH=7.4: 3.340
Log(P): 3.03
Log S: -4.01
Log(Vapor Pressure): -8.71
Melting Point: 191.65
pKa Acid: 8.53
pKa Basic: 4.0

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9233
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9233
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.9046
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.9046
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8889
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8889
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	3	0.8858
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	3	0.8858
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8584
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8584
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8526
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8526
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.8511
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.8511
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8309
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8309
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.8296
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.8296
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8253
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8253
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.8250
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.8250
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8194
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8194
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8122
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8122
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8089
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8089
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8031
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8031
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	3	0.8007
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	3	0.8007
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7988
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7988
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7793
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7793
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7715
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7715
GCN5-related N-acetyltransferase	Q3M362	Q3M362_TRIV2	Trichormus variabilis	3	0.7714
GCN5-related N-acetyltransferase	Q3M362	Q3M362_TRIV2	Trichormus variabilis	3	0.7714
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	4	0.7703
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	4	0.7703
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7702
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7702
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7656
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7656
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7638
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7638
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7597
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7597
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7596
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7596
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7563
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7563
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7561
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7561
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7557
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7557
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7548
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7548
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7506
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7506
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7482
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7482
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7467
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7467
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7456
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7456
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7448
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7448
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	3	0.7432
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	3	0.7432
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7423
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7423
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7417
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7417
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7409
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7409
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7400
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7400
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7382
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7382
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7366
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7366
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7360
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7360
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7349
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7349
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7336
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7336
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7318
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7318
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7279
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7279
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7267
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7267
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7254
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7254
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7234
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7234
Adenosine monophosphate-protein transferase	Q8ZVF7	Q8ZVF7_PYRAE	Pyrobaculum aerophilum	3	0.7188
Adenosine monophosphate-protein transferase	Q8ZVF7	Q8ZVF7_PYRAE	Pyrobaculum aerophilum	3	0.7188
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7185
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7185
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7177
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7177
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7169
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7169
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7166
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7166
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7133
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7133
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7118
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7118
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7094
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7094
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7090
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7090
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7018
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7018

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