Macommelinol - Compound Card

Macommelinol

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Macommelinol

Structure
Zoomed Structure
  • Family: Fungi - Pleosporineae
  • Kingdom: Fungi
  • Class: Alpha-Pyrone Derivative
Canonical Smiles OCCc1c(OC)cc(=O)oc1C
InChI InChI=1S/C9H12O4/c1-6-7(3-4-10)8(12-2)5-9(11)13-6/h5,10H,3-4H2,1-2H3
InChIKey DEBQSJUOQKVEJG-UHFFFAOYSA-N
Formula C9H12O4
HBA 4
HBD 1
MW 184.19
Rotatable Bonds 3
TPSA 59.67
LogP 0.49
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 13
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 184.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Alternaria phragmospora Pleosporineae Fungi 570713

Showing of synonyms

  • Metwaly AM, Fronczek FR, et al. (2014). Antileukemic alpha-pyrone derivatives from the endophytic fungus Alternaria phragmospora. Tetrahedron Letters,2014,55(24),3478-3481. [View]
Pubchem: 14077395
Nmrshiftdb2: 70100694

No compound-protein relationship available.

Structure

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 184.19 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.77
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
25.79
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.36
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.56
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.3
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.46
Rat (Acute)
2.11
Rat (Chronic Oral)
1.77
Fathead Minnow
3.61
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
302.2
Hydration Free Energy
-9.62
Log(D) at pH=7.4
0.13
Log(P)
-0.31
Log S
-0.77
Log(Vapor Pressure)
-3.97
Melting Point
93.47
pKa Acid
9.92
pKa Basic
5.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9811
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9811
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9696
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9696
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9175
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9175
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9110
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9110
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9017
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9017
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8978
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8978
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8968
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8968
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8796
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8796
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8794
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8794
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8787
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8787
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8755
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8755
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8711
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8711
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8708
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8708
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8680
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8680
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8624
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8624
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8513
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8513
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8380
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8380
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8338
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8338
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8299
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8299
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8287
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8287
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.8049
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.8049
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8009
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8009
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7933
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7933
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7929
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7929
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7818
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7818
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7716
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7716
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7705
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7705
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7661
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7661
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7614
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7614
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7598
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7598
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7562
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7562
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7548
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7548
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7525
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7525
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7509
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7509
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7456
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7456
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7453
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7453
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7445
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7445
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7442
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7442
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 3 0.7421
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 3 0.7421
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7408
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7408
Ribonucleoside-diphosphate reductase large chain 1 P21524 RIR1_YEAST Saccharomyces cerevisiae 3 0.7405
Ribonucleoside-diphosphate reductase large chain 1 P21524 RIR1_YEAST Saccharomyces cerevisiae 3 0.7405
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7370
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7370
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7334
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7334
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7329
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7329
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7319
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7319
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 3 0.7298
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 3 0.7298
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7274
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7274
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7257
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7257
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 2 0.7240
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 2 0.7240
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7235
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7235
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 3 0.7224
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 3 0.7224
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7206
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7206
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7198
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7198
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7190
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7190
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7172
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7172
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7133
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7133
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7096
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7096
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7067
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7067
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7067
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7067
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7059
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7059
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7057
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7057
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7054
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7054
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7052
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7052
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7042
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7042
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7041
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7041
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 3 0.7040
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 3 0.7040
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7010
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7010
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7003
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7003

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