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Aspergillus diketopiperazine 11

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

Canonical Smiles	CC[C@H]([C@@H]1NC(=O)[C@H]2N(C1=O)CCC2)C
InChI	InChI=1S/C11H18N2O2/c1-3-7(2)9-11(15)13-6-4-5-8(13)10(14)12-9/h7-9H,3-6H2,1-2H3,(H,12,14)/t7-,8+,9+/m1/s1
InChIKey	ZDACRNZBFJOLTC-VGMNWLOBSA-N
Formula	C₁₁H₁₈N₂O₂
HBA	2
HBD	1
MW	210.28
Rotatable Bonds	2
TPSA	49.41
LogP	0.52
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	15
Formal Charge	0
Fraction CSP3	0.82
Exact Mass	210.14
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: 13654639

Zinc: ZINC000014950844

Nmrshiftdb2: 70049676

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 210.28 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -5.01
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.22
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.46

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.12
Plasma Protein Binding: 25.26
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.38
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.04
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.67
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 2.98
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: -0.31
Rat (Acute): 2.23
Rat (Chronic Oral): 1.99
Fathead Minnow: 3.35
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: 344.73
Hydration Free Energy: -11.36
Log(D) at pH=7.4: 0.85
Log(P): 0.61
Log S: -1.53
Log(Vapor Pressure): -5.34
Melting Point: 126.84
pKa Acid: 8.56
pKa Basic: 6.19

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9093
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9093
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8178
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8178
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.8003
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.8003
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7869
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7869
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7865
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7865
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7832
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7832
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7804
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7804
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7792
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7792
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7774
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7774
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7707
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7707
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7645
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7645
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7605
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7605
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7583
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7583
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7575
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7575
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7548
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7548
Predicted acetyltransferase	Q97ML2	Q97ML2_CLOAB	Clostridium acetobutylicum	3	0.7471
Predicted acetyltransferase	Q97ML2	Q97ML2_CLOAB	Clostridium acetobutylicum	3	0.7471
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7410
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7410
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7328
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7328
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7261
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7261
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7193
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7193
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7173
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7173
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7131
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7131
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	2	0.7123
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	2	0.7123
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7093
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7093
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7072
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7072
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7068
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7068
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7060
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7060
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7013
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7013

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