Terretrione A - Compound Card

Terretrione A

Select a section from the left sidebar

Terretrione A

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
Canonical Smiles CC(CC1N(C)C(=O)C(C(=O)N(C1=O)C)Cc1ccccc1)C
InChI InChI=1S/C18H24N2O3/c1-12(2)10-15-18(23)20(4)17(22)14(16(21)19(15)3)11-13-8-6-5-7-9-13/h5-9,12,14-15H,10-11H2,1-4H3
InChIKey KJGWAOPELYGWFA-UHFFFAOYSA-N
Formula C18H24N2O3
HBA 3
HBD 0
MW 316.4
Rotatable Bonds 4
TPSA 57.69
LogP 1.72
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 316.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Penicillium vinaceum Trichocomaceae Fungi 69790

Showing of synonyms

  • Asiri IAM, Badr JM, et al. (2015). Penicillivinacine, antimigratory diketopiperazine alkaloid from the marine-derived fungus Penicillium vinaceum. Phytochemistry Letters,2015,13,53-58. [View]
Pubchem: 71480550
Nmrshiftdb2: 70020988

No compound-protein relationship available.

Structure

SMILES: N1C(=O)CNC(=O)C(C1=O)Cc2ccccc2

Level: 1

Mol. Weight: 316.4 g/mol

Structure

SMILES: O=C1CC(=O)NCC(=O)N1

Level: 0

Mol. Weight: 316.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 316.4 g/mol

Antimicrobial
Antimigratory

Absorption

Caco-2 (logPapp)
-4.29
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.36
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
41.93
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.01
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.82
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
2.26
Rat (Acute)
2.92
Rat (Chronic Oral)
1.75
Fathead Minnow
3.73
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
359.31
Hydration Free Energy
-10.74
Log(D) at pH=7.4
1.5
Log(P)
2.79
Log S
-2.37
Log(Vapor Pressure)
-6.81
Melting Point
115.57
pKa Acid
8.76
pKa Basic
6.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8500
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8500
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8345
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8345
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8229
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8229
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8150
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8150
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8106
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8106
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7975
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7975
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7968
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7968
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7942
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7942
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7713
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7713
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7708
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7708
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7682
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7682
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7640
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7640
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7624
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7624
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7592
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7592
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7565
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7565
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7564
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7564
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7510
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7510
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7509
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7509
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7503
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7503
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7484
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7484
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7482
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7482
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7471
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7471
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7465
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7465
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7437
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7437
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7410
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7410
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7375
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7375
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7361
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7361
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7341
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7341
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7339
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7339
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7323
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7323
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7312
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7312
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7310
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7310
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7306
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7306
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7304
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7304
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7298
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7298
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7287
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7287
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7279
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7279
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7272
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7272
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7242
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7242
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7238
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7238
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7221
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7221
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7221
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7221
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7214
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7214
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7185
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7185
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7180
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7180
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7178
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7178
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7166
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7166
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7162
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7162
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7146
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7146
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7141
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7141
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7132
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7132
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7118
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7118
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7106
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7106
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7087
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7087
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 2 0.7068
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 2 0.7068
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7061
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7061
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7058
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7058
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7057
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7057
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7057
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7057
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7030
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7030
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7023
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7023
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7014
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7014
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7009
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7009

Download SDF