Fumitremorgin C - Compound Card

Fumitremorgin C

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Fumitremorgin C

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Diketopiperazine
Canonical Smiles COc1ccc2c(c1)[nH]c1c2C[C@@H]2N([C@H]1C=C(C)C)C(=O)[C@H]1N(C2=O)CCC1
InChI InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1
InChIKey DBEYVIGIPJSTOR-FHWLQOOXSA-N
Formula C22H25N3O3
HBA 3
HBD 1
MW 379.46
Rotatable Bonds 2
TPSA 65.64
LogP 2.94
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 379.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus fumigatus Trichocomaceae Fungi 746128

Showing of synonyms

  • El-Gendy BEDM, Rateb ME (2015). Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification. Bioorganic and Medicinal Chemistry Letters,2015,25(16),3125-3128. [View] [PubMed]
CPRiL: 101492
Structure

SMILES: c1cccc2[nH]c(c3c12)CN4C(C3)C(=O)N5C(C4=O)CCC5

Level: 0

Mol. Weight: 379.46 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.76

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
62.46
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.590
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.220
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.670
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.550
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
-22.930
Rat (Acute)
2.360
Rat (Chronic Oral)
2.220
Fathead Minnow
4.360
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
513.230
Hydration Free Energy
-5.960
Log(D) at pH=7.4
2.350
Log(P)
2.84
Log S
-4.02
Log(Vapor Pressure)
-10.0
Melting Point
258.69
pKa Acid
10.78
pKa Basic
5.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9811
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9811
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9375
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9375
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9076
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9076
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8981
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8981
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8975
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8975
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8951
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8951
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8869
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8869
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8652
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8652
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8596
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8596
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8479
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8479
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8458
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8458
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8408
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8408
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8378
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8378
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8369
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8369
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8348
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8348
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8288
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8288
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7613
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7613
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7590
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7590
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7571
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7571
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7507
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7507
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7504
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7504
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7437
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7437
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7427
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7427
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7412
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7412
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7351
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7351
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7344
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7344
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7330
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7330
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7325
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7325
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7318
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7318
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7307
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7307
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7302
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7302
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7296
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7296
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7281
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7281
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7272
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7272
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7265
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7265
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7265
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7265
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7233
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7233
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7221
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7221
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7215
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7215
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7209
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7209
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7184
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7184
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7182
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7182
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7172
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7172
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7164
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7164
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7161
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7161
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7159
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7159
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7152
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7152
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7147
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7147
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7139
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7139
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7132
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7132
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7127
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7127
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7108
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7108
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7098
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7098
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7069
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7069
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7068
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7068
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7065
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7065
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7062
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7062
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7054
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7054
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7052
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7052
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7052
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7052
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7051
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7051
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7049
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7049
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7040
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7040
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7035
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7035
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7035
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7035
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7028
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7028
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7019
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7019
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7009
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7009
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7003
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7003
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7001
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7001

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