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Butyrolactone-V

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Lignan
- Subclass: Dibenzylbutyrolactone Lignan

Canonical Smiles	COC(=O)[C@]1(Cc2ccc3c(c2)C[C@@H](C(O3)(C)C)O)OC(=O)C(=C1c1ccc(cc1)O)O
InChI	InChI=1S/C24H24O8/c1-23(2)18(26)11-15-10-13(4-9-17(15)31-23)12-24(22(29)30-3)19(20(27)21(28)32-24)14-5-7-16(25)8-6-14/h4-10,18,25-27H,11-12H2,1-3H3/t18-,24+/m0/s1
InChIKey	NSXYYYUKWBLFQH-MHECFPHRSA-N
Formula	C₂₄H₂₄O₈
HBA	8
HBD	3
MW	440.45
Rotatable Bonds	4
TPSA	122.52
LogP	2.45
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	440.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspergillus terreus	Trichocomaceae	Fungi	33178
2	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]
Hamed A, Ismail M, et al. (2019). X-ray, structural assignment and molecular docking study of dihydrogeodin from Aspergillus Terreus TM8. Nat Prod Res,2019,33(1),117-121. [View] [PubMed]

Pubchem: 70685955

Cas: 1151509-01-1

Zinc: ZINC000084724161

Nmrshiftdb2: 70046694

Chembl: CHEMBL2035563

No compound-protein relationship available.

SMILES: C1CCOc(c12)ccc(c2)CC3OC(=O)C=C3c4ccccc4

Level: 2

Mol. Weight: 440.45 g/mol

SMILES: O=C1C=CC(O1)Cc(c2)ccc(c23)OCCC3

Level: 1

Mol. Weight: 440.45 g/mol

SMILES: C1OC(=O)C=C1c2ccccc2

Level: 1

Mol. Weight: 440.45 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 440.45 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 440.45 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 440.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.38
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.870
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.62

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.980
Plasma Protein Binding: 71.11
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.120
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.060
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.440
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.960
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: -68.060
Rat (Acute): 2.380
Rat (Chronic Oral): 2.720
Fathead Minnow: 4.770
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: 485.480
Hydration Free Energy: -2.890
Log(D) at pH=7.4: 2.550
Log(P): 2.36
Log S: -3.68
Log(Vapor Pressure): -9.35
Melting Point: 214.68
pKa Acid: 7.56
pKa Basic: 3.39

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9434
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9434
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.9157
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.9157
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.8792
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.8792
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8700
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8700
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8487
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8487
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8475
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8475
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8423
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8423
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.8294
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.8294
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8079
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8079
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8065
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8065
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8054
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8054
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7983
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7983
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.7935
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.7935
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7893
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7893
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.7818
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.7818
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7755
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7755
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7743
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7743
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7735
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7735
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7580
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7580
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7544
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7544
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7539
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7539
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7531
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7531
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7519
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7519
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7489
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7489
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7474
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7474
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7460
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7460
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7450
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7450
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7420
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7420
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7419
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7419
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7394
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7394
Cholesterol side-chain cleavage enzyme, mitochondrial	P00189	CP11A_BOVIN	Bos taurus	4	0.7380
Cholesterol side-chain cleavage enzyme, mitochondrial	P00189	CP11A_BOVIN	Bos taurus	4	0.7380
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7366
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7366
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	3	0.7361
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	3	0.7361
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7343
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7343
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7334
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7334
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7332
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7332
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7318
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7318
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7313
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7313
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7312
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7312
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7312
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7312
Threonine synthase 1, chloroplastic	Q9S7B5	THRC1_ARATH	Arabidopsis thaliana	3	0.7182
Threonine synthase 1, chloroplastic	Q9S7B5	THRC1_ARATH	Arabidopsis thaliana	3	0.7182
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7160
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7160
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	4	0.7136
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	4	0.7136
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7125
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7125
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7117
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7117
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	3	0.7083
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	3	0.7083
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7067
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7067
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7067
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7067
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7032
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7032
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7016
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7016
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7010
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7010

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