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Cyclo(Phe-Pro)
- Family: Plantae - Solanaceae
- Kingdom: Plantae
-
Class: Peptide
- Subclass: Cyclic Dipeptide
| Canonical Smiles | O=C1NC(Cc2ccccc2)C(=O)N2C1CCC2 |
|---|---|
| InChI | InChI=1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17) |
| InChIKey | QZBUWPVZSXDWSB-UHFFFAOYSA-N |
| Formula | C14H16N2O2 |
| HBA | 2 |
| HBD | 1 |
| MW | 244.29 |
| Rotatable Bonds | 2 |
| TPSA | 49.41 |
| LogP | 0.72 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.43 |
| Exact Mass | 244.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Solanum nigrum | Solanaceae | Plantae | 4112 |
Showing of synonyms
Cyclo(Phe-Pro)
14705-60-3
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-
Cyclo(D-phenylalanyl-L-prolyl)
Cyclo(L-prolyl-D-phenylalanyl)
3-benzyl-octahydropyrrolo[1,2-a]pyrazine-1,4-dione
A 64863
3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Pyrrolo(2,1-f)pyrazine-1,4-dione, 2,3,6,7,8,8a-hexahydro-3-(phenylmethyl)-
NSC646119
Cyclo(phenylalanylprolyl)
Phe-pro-diketopiperazine
MFCD00038604
L-Phe-D-Pro lactam
NSC 255998
(3S-trans)-3-Benzylhexahydropyrrolo(1,2-a)pyrazine-1,4-dione
SCHEMBL173749
Cyclo-Phe-Pro-diketopiperazine
MEGxm0_000490
CHEMBL1990465
ACon0_001420
DTXSID30933019
(3R,8aS)-3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
CHEBI:201642
QZBUWPVZSXDWSB-UHFFFAOYSA-N
BCP32901
HY-P1934
EINECS 223-047-0
NSC255998
PYRROLO[1,2-A]PYRAZINE-1,4-DIONE,HEXAHYDRO-3-(PHENYLMETHYL)-
3-(Phenylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo(2,1-f)pyrazine-1,4-dione
AKOS015999981
NSC-255998
NSC-646119
NCGC00380633-02
AS-71116
DA-52218
FC165809
NCI60_015870
SY045657
DB-049055
CS-0064705
NS00097186
D92888
Cyclo(-Phe-Pro)
Cyclo-L-phenylalanyl-L-proline
3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione #
3-BENZYL-HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE
Pyrrolo[1,4-dione, hexahydro-3-(phenylmethyl)-, (3R-cis)-
3-Benzyl-1-hydroxy-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazin-4(3H)-one
Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-, (3R-cis)-
NCGC00380633-02_C14H16N2O2_Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-
CPRiL:
88756
SMILES: c1ccccc1CC(NC2=O)C(=O)N(C23)CCC3
Level: 1
Mol. Weight: 244.29 g/mol
SMILES: C1CCN(C12)C(=O)CNC2=O
Level: 0
Mol. Weight: 244.29 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 244.29 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.71
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.18
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.78
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.46
- Plasma Protein Binding
- 49.05
- 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
- 5.07
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.59
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.38
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.84
- 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
- 2.56
- Rat (Acute)
- 2.21
- Rat (Chronic Oral)
- 2.18
- Fathead Minnow
- 3.83
- 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
- 376.1
- Hydration Free Energy
- -13.83
- Log(D) at pH=7.4
- 1.18
- Log(P)
- 0.95
- Log S
- -1.94
- Log(Vapor Pressure)
- -7.21
- Melting Point
- 156.84
- pKa Acid
- 8.95
- pKa Basic
- 5.52
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial | Q33862 | Q33862_ASCSU | Ascaris suum | 3 | 0.9778 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.9533 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.9400 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.9355 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.9215 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8934 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8799 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8733 |
| Cytochrome P450 | S6BVH1 | S6BVH1_RHOER | Rhodococcus erythropolis | 3 | 0.8693 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8689 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8552 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8432 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8431 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8427 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8307 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.8099 |
| Gag-Pol polyprotein | P03369 | POL_HV1A2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8097 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8063 |
| Epoxide hydrolase | Q41415 | Q41415_SOLTU | Solanum tuberosum | 3 | 0.7997 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7978 |
| HLA class I histocompatibility antigen, B alpha chain | P01889 | HLAB_HUMAN | Homo sapiens | 3 | 0.7962 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7903 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.7897 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7878 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7861 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 3 | 0.7858 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7747 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7743 |
| Amine oxidase [flavin-containing] B | P27338 | AOFB_HUMAN | Homo sapiens | 3 | 0.7710 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7702 |
| Multidrug transporter MdfA | P0AEY8 | MDFA_ECOLI | Escherichia coli | 3 | 0.7701 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7681 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7639 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7609 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7601 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7601 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7585 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7574 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7574 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7542 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7539 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7535 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 2 | 0.7514 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7475 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7426 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7417 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 2 | 0.7381 |
| Flavin reductase like domain-containing protein | Q4UKE8 | Q4UKE8_RICFE | Rickettsia felis | 3 | 0.7355 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7335 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7333 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 2 | 0.7333 |
| Type II methyltransferase M.RsrI | P14751 | MTR1_RHOSH | Cereibacter sphaeroides | 3 | 0.7308 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.7302 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7295 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7277 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7273 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7248 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7242 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7228 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7204 |
| Penicillin V acylase | P12256 | PAC_LYSSH | Lysinibacillus sphaericus | 3 | 0.7196 |
| Glucocorticoid receptor | P04150 | GCR_HUMAN | Homo sapiens | 3 | 0.7191 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7188 |
| Phenylpyruvate C(3)-methyltransferase | Q643C8 | MPPJ_STRHY | Streptomyces hygroscopicus | 2 | 0.7180 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7173 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7167 |
| Putative snRNP Sm-like protein | Q8ZYG5 | Q8ZYG5_PYRAE | Pyrobaculum aerophilum | 2 | 0.7135 |
| Glutaminyl-peptide cyclotransferase | Q16769 | QPCT_HUMAN | Homo sapiens | 3 | 0.7127 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7122 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7120 |
| Adenosine kinase | Q9TVW2 | ADK_TOXGO | Toxoplasma gondii | 2 | 0.7112 |
| 4-hydroxyphenylacetate 3-monooxygenase, reductase component | Q5SJP7 | HPAC_THET8 | Thermus thermophilus | 3 | 0.7087 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.7058 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7048 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7046 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 2 | 0.7031 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7030 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7026 |
| Adenosine kinase | Q9TVW2 | ADK_TOXGO | Toxoplasma gondii | 3 | 0.7016 |
| Ribonuclease 4 | P15468 | RNAS4_PIG | Sus scrofa | 2 | 0.7004 |