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Aspergillus diketopiperazine 9
- Family: Plantae - Solanaceae
- Kingdom: Fungi, Plantae
-
Class: Alkaloid
- Subclass: Diketopiperazine
| Canonical Smiles | CC(C[C@@H]1NC(=O)[C@H]2N(C1=O)CCC2)C |
|---|---|
| InChI | InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9-/m0/s1 |
| InChIKey | SZJNCZMRZAUNQT-IUCAKERBSA-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 |
| 2 | Dendrothyrium variisporum | Montagnulaceae | Fungi | 1985348 |
| 3 | Solanum nigrum | Solanaceae | Plantae | 4112 |
Showing of synonyms
Aspergillus diketopiperazine 9
2873-36-1
Cyclo(-Leu-Pro)
Cyclo(L-leu-L-pro)
(3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Gancidin W
Cyclo(Leu-Pro)
Cyclo(L-prolyl-L-leucyl)
Cyclo-L-leu-L-pro
Cyclo(L-leucyl-L-prolyl)
L-Leucyl-L-proline lactam
L-cyclo(Leu-pro)
L-cyclo(Leucyloprolyl)
L,L-Cyclo(leucylprolyl)
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-, (3S,8aS)-
(3S,8aS)-3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Maculosin 6
Cyclo(leucyl-prolyl)
Cyclo(L-Pro-L-Leu)
KQV8MY059B
SZJNCZMRZAUNQT-IUCAKERBSA-N
MFCD00237617
Cyclo-(L-Pro-L-Leu)
Cyclo(-L-Leu-L-Pro)
Cyclo(-L-leucyl-prolyl)
CHEMBL508326
SCHEMBL2037800
DTXSID80951384
CHEBI:133094
BDBM163709
HY-P1939
Cyclo L-Pro-L-Leu (Fr. 1-6)
AKOS024463311
FC20681
AS-40794
DA-72469
CS-0065365
NS00049404
EN300-28258032
(3S,8aS)-3-(2-methylpropyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
(3S,8AS)-3-(2-METHYLPROPYL)-HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE
(3S,8aS)-3-isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Rac-(3R,8aR)-3-(2-methylpropyl)-octahydropyrrolo[1,2-a]pyrazine-1,4-dione
(3S-trans)-Hexahydro-3-(2-methylpropyl)-pyrrolo[1,2-a]pyrazine-1,4-dione
3-Isobutylhexahydropyrrolo [1,2-a] pyrazine-1,4-dione
Cyclo (L-leu-L-pro)
- 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]
- Teponno RB, Noumeur SR, et al. (2017). Furanones and anthranilic acid derivatives from the endophytic fungus Dendrothyrium variisporum. Molecules 2017, 22(10), 1674. [View] [PubMed]
- El-Hawary S.S, Sayed A.M, et al. (2017). Secondary metabolites from fungal endophytes of Solanum nigrum. Natural product research, 2017, 31(21), 2568-2571. [View] [PubMed]
Pubchem:
7074739
Cas:
2873-36-1
Gnps:
CCMSLIB00004684690
Zinc:
ZINC000004023243
Chebi:
133094
Nmrshiftdb2:
60026058
Metabolights:
MTBLC133094
Chembl:
CHEMBL508326
Bindingdb:
163709
CPRiL:
113588
SMILES: C1CCN(C12)C(=O)CNC2=O
Level: 0
Mol. Weight: 210.28 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -5.0
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.23
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.49
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.15
- Plasma Protein Binding
- 26.5
- 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
- 4.8
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.86
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.62
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 2.83
- 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
- 0.95
- Rat (Acute)
- 2.18
- Rat (Chronic Oral)
- 1.98
- Fathead Minnow
- 3.4
- 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
- 342.65
- Hydration Free Energy
- -11.19
- Log(D) at pH=7.4
- 1.15
- Log(P)
- 0.57
- Log S
- -1.59
- Log(Vapor Pressure)
- -5.21
- Melting Point
- 119.89
- pKa Acid
- 8.31
- pKa Basic
- 6.16
| 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 | 0.9224 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.9224 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8823 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8823 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.8453 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.8453 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8353 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8353 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8017 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8017 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7937 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7937 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7909 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7909 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7864 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7864 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7813 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7813 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7783 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7783 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7727 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7727 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7680 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7680 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7670 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7670 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7661 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7661 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7660 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7660 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7631 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7631 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7629 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7629 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7600 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7600 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7591 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7591 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7565 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7565 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7560 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7560 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7505 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7505 |
| Predicted acetyltransferase | Q97ML2 | Q97ML2_CLOAB | Clostridium acetobutylicum | 3 | 0.7397 |
| Predicted acetyltransferase | Q97ML2 | Q97ML2_CLOAB | Clostridium acetobutylicum | 3 | 0.7397 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7271 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7271 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7255 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7255 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7217 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7217 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.7169 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.7169 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7168 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7168 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7160 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7160 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7151 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7151 |