Select a section from the left sidebar
Cleistenolide
- Family: Plantae - Annonaceae
- Kingdom: Plantae
-
Class: Cycloalkene
- Subclass: Lactone Aromatic Ester
| Canonical Smiles | O=C(c1ccccc1)OC[C@@H](C1OC(=O)C=C[C@H]1OC(=O)C)OC(=O)C |
|---|---|
| InChI | InChI=1S/C18H18O8/c1-11(19)24-14-8-9-16(21)26-17(14)15(25-12(2)20)10-23-18(22)13-6-4-3-5-7-13/h3-9,14-15,17H,10H2,1-2H3/t14-,15+,17?/m1/s1 |
| InChIKey | LLQJCQPOMJOCDA-CKDQBVIESA-N |
| Formula | C18H18O8 |
| HBA | 8 |
| HBD | 0 |
| MW | 362.33 |
| Rotatable Bonds | 6 |
| TPSA | 105.2 |
| LogP | 1.19 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.33 |
| Exact Mass | 362.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cleistochlamys kirkii | Annonaceae | Plantae | 1237197 |
Showing of synonyms
Cleistenolide
(-)-Cleistenolide
1003600-48-3
CHEMBL3814668
HY-N10391
DA-68938
CS-0513773
[(2R)-2-acetyloxy-2-[(2S,3R)-3-acetyloxy-6-oxo-2,3-dihydropyran-2-yl]ethyl] benzoate
No compound-protein relationship available.
SMILES: c1ccccc1C(=O)OCCC(O2)CC=CC2=O
Level: 1
Mol. Weight: 362.33 g/mol
SMILES: O=C1C=CCCO1
Level: 0
Mol. Weight: 362.33 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 362.33 g/mol
Anti-plasmodial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.82
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.68
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.74
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.33
- Plasma Protein Binding
- 40.17
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.91
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.85
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.92
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.37
- 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
- -4.37
- Rat (Acute)
- 2.32
- Rat (Chronic Oral)
- 2.41
- Fathead Minnow
- 4.27
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 390.02
- Hydration Free Energy
- -7.28
- Log(D) at pH=7.4
- 1.66
- Log(P)
- 1.48
- Log S
- -3.5
- Log(Vapor Pressure)
- -6.98
- Melting Point
- 97.1
- pKa Acid
- 7.69
- pKa Basic
- 1.57
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9114 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8191 |
| Class B acid phosphatase | Q540U1 | APHA_SALTM | Salmonella typhimurium | 2 | 0.8171 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7889 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7722 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7702 |
| Heat shock cognate 71 kDa protein | P11142 | HSP7C_HUMAN | Homo sapiens | 3 | 0.7629 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7600 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7490 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 4 | 0.7424 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7399 |
| Multidrug efflux pump subunit AcrB | P31224 | ACRB_ECOLI | Escherichia coli | 3 | 0.7378 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7330 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7324 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7273 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7272 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 2 | 0.7262 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7246 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7224 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7203 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 2 | 0.7198 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7179 |
| [LysW]-aminoadipate kinase | O50147 | LYSZ_THET2 | Thermus thermophilus | 3 | 0.7167 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7167 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 2 | 0.7162 |
| Oxygen-insensitive NAD(P)H nitroreductase | P38489 | NFSB_ECOLI | Escherichia coli | 3 | 0.7150 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 2 | 0.7142 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7141 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7139 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 3 | 0.7133 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7130 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7125 |
| Acidic phospholipase A2 3 | P60045 | PA2A3_NAJSG | Naja sagittifera | 2 | 0.7121 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7115 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7112 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7097 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7096 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7089 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7086 |
| Bis(5'-adenosyl)-triphosphatase | P49789 | FHIT_HUMAN | Homo sapiens | 2 | 0.7052 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 2 | 0.7050 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7048 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7032 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 2 | 0.7020 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 2 | 0.7016 |
| Unconventional myosin-Va | Q02440 | MYO5A_CHICK | Gallus gallus | 2 | 0.7015 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7014 |