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)O)CC=C(C)C)OC(=O)C(=C1c1ccc(cc1)O)O
InChI InChI=1S/C24H24O7/c1-14(2)4-6-16-7-5-15(12-19(16)26)13-24(23(29)30-3)20(21(27)22(28)31-24)17-8-10-18(25)11-9-17/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m1/s1
InChIKey QOOYPQVHNJRXEX-XMMPIXPASA-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 terreus Trichocomaceae Fungi 33178

Showing of synonyms

  • Awaad AS, Nabilah AJ, et al. (2012). New antifungal compounds from Aspergillus terreus isolated from desert soil. Phytotherapy Research,2012,26(12),1872-1877. [View] [PubMed]
Pubchem: 163088030
Nmrshiftdb2: 80017711
CPRiL: 101537
Structure

SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3

Level: 2

Mol. Weight: 424.45 g/mol

Structure

SMILES: O=C1C=CC(O1)Cc2ccccc2

Level: 1

Mol. Weight: 424.45 g/mol

Structure

SMILES: C1OC(=O)C=C1c2ccccc2

Level: 1

Mol. Weight: 424.45 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 424.45 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 424.45 g/mol

Antifungal

Absorption

Caco-2 (logPapp)
-5.27
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
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.040
Plasma Protein Binding
62.81
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
7.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.120
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.640
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.450
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
-33.370
Rat (Acute)
2.120
Rat (Chronic Oral)
2.970
Fathead Minnow
5.140
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
479.640
Hydration Free Energy
-3.790
Log(D) at pH=7.4
3.300
Log(P)
3.39
Log S
-4.16
Log(Vapor Pressure)
-8.83
Melting Point
195.43
pKa Acid
8.13
pKa Basic
4.72
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 0.9542
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9542
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9088
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9088
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8853
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8853
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8794
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8794
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8775
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8775
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8730
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8730
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8638
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8638
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8634
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8634
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8626
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8626
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8511
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8511
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8436
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8436
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8420
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8420
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8237
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8237
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8140
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8140
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.8067
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8067
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8067
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.8067
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8060
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8060
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8032
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8032
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8016
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8016
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7955
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7955
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7849
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7849
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7846
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7846
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7841
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7841
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7801
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7801
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7731
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7731
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7670
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7670
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7665
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7665
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7665
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7665
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7653
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7653
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7629
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7629
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7621
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7621
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7590
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7590
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7590
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7590
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7556
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7556
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7536
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7536
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7534
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7534
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7531
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7531
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7519
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7519
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7493
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7493
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7477
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7477
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7449
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7449
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7448
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7448
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7328
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7328
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7319
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7319
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7313
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7313
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7221
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7221
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7220
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7188
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7188
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7174
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7174
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7170
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7170
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7143
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7143
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7113
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7113
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7111
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7111
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7110
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7110
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7107
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7107
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7104
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7104
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 3 0.7097
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 3 0.7097
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7084
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7084
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7083
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7083
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7071
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7071
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7052
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7052
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7038
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7038
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7033
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7033
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7030
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7030
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7028
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7028
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 2 0.7021
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 2 0.7021
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7013
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7013

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