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Tryprostatin B

Family: Fungi - Trichocomaceae
Kingdom: Fungi
Class: Alkaloid
- Subclass: Diketopiperazine

Canonical Smiles	CC(=CCc1[nH]c2c(c1C[C@@H]1NC(=O)[C@H]3N(C1=O)CCC3)cccc2)C
InChI	InChI=1S/C21H25N3O2/c1-13(2)9-10-17-15(14-6-3-4-7-16(14)22-17)12-18-21(26)24-11-5-8-19(24)20(25)23-18/h3-4,6-7,9,18-19,22H,5,8,10-12H2,1-2H3,(H,23,25)/t18-,19-/m0/s1
InChIKey	GLWYBXPXOSKQAW-OALUTQOASA-N
Formula	C₂₁H₂₅N₃O₂
HBA	2
HBD	2
MW	351.45
Rotatable Bonds	4
TPSA	65.2
LogP	2.71
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	351.19
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]

Pubchem: 9863281

Cas: 179936-52-8

Gnps: CCMSLIB00005727277

Chebi: 72760

Nmrshiftdb2: 60073766

Metabolights: MTBLC72760

Chembl: CHEMBL36668

Comptox: DTXSID40893998

CPRiL: 216339

SMILES: C1CCN(C12)C(=O)C(NC2=O)Cc3c[nH]c(c34)cccc4

Level: 1

Mol. Weight: 351.45 g/mol

SMILES: C1CCN(C12)C(=O)CNC2=O

Level: 0

Mol. Weight: 351.45 g/mol

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 351.45 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -4.9
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.73
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.12

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.87
Plasma Protein Binding: 71.81
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-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: 7.1
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.06
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.93
Liver Injury II: Toxic
hERG Blockers: Toxic
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: -6.8
Rat (Acute): 2.57
Rat (Chronic Oral): 2.49
Fathead Minnow: 4.25
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 484.14
Hydration Free Energy: -9.62
Log(D) at pH=7.4: 2.81
Log(P): 3.04
Log S: -4.12
Log(Vapor Pressure): -10.3
Melting Point: 209.33
pKa Acid: 10.12
pKa Basic: 5.49

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9457
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9457
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8994
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8994
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8977
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8977
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8923
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8923
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8666
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8666
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8558
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8558
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8312
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8312
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.8190
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.8190
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8173
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8173
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8163
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8163
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8098
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8098
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7991
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7991
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7986
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7986
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.7891
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.7891
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7829
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7829
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7796
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7796
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7795
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7795
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7750
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7750
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7740
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7740
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7738
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7738
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7734
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7734
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7629
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7629
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7628
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7628
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7604
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7604
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7604
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7604
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7595
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7595
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7586
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7586
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7573
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7573
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7539
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7539
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7505
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7505
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7465
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7465
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7458
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7458
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7452
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7452
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7404
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7404
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7396
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7396
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7383
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7383
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7378
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7378
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7371
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7371
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7353
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7353
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7348
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7348
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7341
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7341
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7334
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7334
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7305
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7305
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7305
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7305
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7287
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7287
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7283
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7283
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7254
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7254
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7253
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7253
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7242
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7242
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7229
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7229
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7217
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7217
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7212
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7212
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7199
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7199
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7184
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7184
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7184
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7184
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7174
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7174
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7167
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7167
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	2	0.7164
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	2	0.7164
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7149
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7149
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7148
Regucalcin	Q64374	RGN_MOUSE	Mus musculus	3	0.7148
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7148
Regucalcin	Q64374	RGN_MOUSE	Mus musculus	3	0.7148
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7147
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7147
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7120
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7120
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7113
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7113
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7105
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7105
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7102
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7102
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7100
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7100
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7099
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7099
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7099
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7099
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7098
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7098
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7096
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7096
Archaeal actin homolog	Q9HKL4	ACTH_THEAC	Thermoplasma acidophilum	2	0.7077
Archaeal actin homolog	Q9HKL4	ACTH_THEAC	Thermoplasma acidophilum	2	0.7077
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7073
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7073
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7066
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7066
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7046
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7046
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7029
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7029
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7023
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7023
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7020
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7020
Plasmid segregation protein ParM	P11904	PARM_ECOLX	Escherichia coli	3	0.7013
Plasmid segregation protein ParM	P11904	PARM_ECOLX	Escherichia coli	3	0.7013
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7008
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7008
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7002
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7002

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