Butyrolactone I - Compound Card

Butyrolactone I

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Butyrolactone I

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Lactone
    • Subclass: Butyrolactone Derivative
Canonical Smiles COC(=O)[C@]1(Cc2ccc(c(c2)C=C(C)C)O)OC(=O)C(=C1c1ccc(cc1)O)O
InChI InChI=1S/C23H22O7/c1-13(2)10-16-11-14(4-9-18(16)25)12-23(22(28)29-3)19(20(26)21(27)30-23)15-5-7-17(24)8-6-15/h4-11,24-26H,12H2,1-3H3/t23-/m1/s1
InChIKey SGIGWFGUUMVHJH-HSZRJFAPSA-N
Formula C23H22O7
HBA 7
HBD 3
MW 410.42
Rotatable Bonds 5
TPSA 113.29
LogP 3.5
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 410.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus terreus Trichocomaceae Fungi 33178

Showing of synonyms

  • Chen H, Daletos G, et al. (2015). Inducing secondary metabolite production by the soil-dwelling fungus Aspergillus terreus through bacterial co-culture. Phytochemistry Letters,2015,12,35-41. [View]
Pubchem: 162926270
Nmrshiftdb2: 70007034
CPRiL: 101537
Structure

SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3

Level: 2

Mol. Weight: 410.42 g/mol

Structure

SMILES: O=C1C=CC(O1)Cc2ccccc2

Level: 1

Mol. Weight: 410.42 g/mol

Structure

SMILES: C1OC(=O)C=C1c2ccccc2

Level: 1

Mol. Weight: 410.42 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 410.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 410.42 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.010
Plasma Protein Binding
62.2
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.940
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.270
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.480
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.290
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
-18.220
Rat (Acute)
2.170
Rat (Chronic Oral)
2.980
Fathead Minnow
4.960
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
478.780
Hydration Free Energy
-5.710
Log(D) at pH=7.4
3.160
Log(P)
2.69
Log S
-4.0
Log(Vapor Pressure)
-8.5
Melting Point
205.22
pKa Acid
8.36
pKa Basic
3.19
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 0.9463
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9463
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8819
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8819
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8671
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8671
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8575
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8575
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8487
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8487
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8471
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8471
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8341
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8341
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8199
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8199
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7969
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7969
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7937
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7937
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7895
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7895
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7827
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7827
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7732
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7732
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7721
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7721
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7720
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7720
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7708
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7708
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7683
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7683
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7670
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7670
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7599
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7599
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7573
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7573
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7563
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7563
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7453
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7453
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7448
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7448
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7432
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7432
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7414
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7414
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7409
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7409
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7391
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7391
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7390
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7390
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7364
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7364
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7356
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7356
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7274
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7274
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7245
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7245
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7235
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7235
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7225
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7225
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7216
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7216
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7203
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7203
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7185
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7185
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7152
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7152
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 3 0.7142
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 3 0.7142
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7110
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7110
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7100
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7100
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7088
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7088
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7082
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7082
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7078
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7078
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7058
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7058
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7054
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7054
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7053
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7053
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7049
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7049
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7033
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7033
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7030
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7030
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7025
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7025
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7019
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7019
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7010
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7010
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 3 0.7002
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 3 0.7002

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