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(-)-crotepoxide
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Cyclic Compound
- Subclass: Cyclohexane Derivative
| Canonical Smiles | CC(=O)O[C@H]1[C@H](OC(=O)C)[C@H]2O[C@H]2[C@@H]2[C@@]1(COC(=O)c1ccccc1)O2 |
|---|---|
| InChI | InChI=1S/C18H18O8/c1-9(19)23-13-12-14(25-12)16-18(26-16,15(13)24-10(2)20)8-22-17(21)11-6-4-3-5-7-11/h3-7,12-16H,8H2,1-2H3/t12-,13-,14-,15+,16-,18+/m1/s1 |
| InChIKey | ASAWUXMEXFAFMU-DBDULZNHSA-N |
| Formula | C18H18O8 |
| HBA | 8 |
| HBD | 0 |
| MW | 362.33 |
| Rotatable Bonds | 5 |
| TPSA | 103.96 |
| LogP | 0.63 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 362.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Friesodielsia obovata | Annonaceae | Plantae | 1202418 |
| 2 | Croton alienus | Euphorbiaceae | Plantae | 100370 |
| 3 | Croton macrostachyus | Euphorbiaceae | Plantae | 1704622 |
| 4 | Croton macrostachys | Euphorbiaceae | Plantae | 1704622 |
| 5 | Croton macrostachys | Euphorbiaceae | Plantae | 1704622 |
Showing of synonyms
(-)-crotepoxide
Crotepoxide
Futoxide
[(1R,2R,4R,5S,6R,7S)-5,6-diacetyloxy-3,8-dioxatricyclo[5.1.0.02,4]octan-4-yl]methyl benzoate
4-((Benzoyloxy)methyl)3,8-dioxatricyclo(5.1.0.0)-octane-5,6-diol diacetate
((1R,2R,4R,5S,6R,7S)-5,6-diacetyloxy-3,8-dioxatricyclo(5.1.0.02,4)octan-4-yl)methyl benzoate
20421-13-0
Crotepoxide (Futoxide)
NSC106396
CHEMBL1976475
DTXSID201318179
C18H18O8
AKOS040740389
NSC-106396
NCI60_000149
AA-504/21163045
AK-693/21159013
3,4)]octane-5,6-diol, 4-(hydroxymethyl)-, 5,6-diacetate 4-benzoate
[(1R,2R,4R,5S,6R,7S)-5,6-diacetoxy-3,8-dioxatricyclo[5.1.0.02,4]octan-4-yl]methyl benzoate
- Joseph CC, Magadula JJ, et al. (2007). A novel antiplasmodial 3',5'-diformylchalcone and other constituents of Friesodielsia obovata. Natural Product Research,2007,21(11),1009-1015. [View] [PubMed]
- Ndunda B, Langat MK, et al. (2013). Alienusolin, a new 4α-deoxyphorbol ester derivative, and crotonimide C, a new glutarimide alkaloid from the Kenyan Croton alienus.. Planta Med,2013,79(18),1762-1766. [View] [PubMed]
- Yibralign Z, Fiseha A. (2007). Phytochemical investigation on the stem bark of Croton macrostachyus (Bisana). M.Sc. Thesis, Addis Ababa University, Ethiopia,2007. [View] [PubMed]
- Kupchan SM, Hemingway RJ, et al. (1969). Tumor inhibitors. XLV. Crotepoxide, a novel cyclohexane diepoxide tumor inhibitor from Croton macrostachys.. The Journal of organic chemistry,1969,34(12),3898-3902. [View] [PubMed]
- Kupchan SM, Hemingway RJ, et al. (1968). Tumor inhibitors. XXIX. Crotepoxide, a novel cyclohexane diepoxide tumor inhibitor from croton macrostachys.. Journal of the American Chemical Society,1968,90(11),2982-2983. [View] [PubMed]
CPRiL:
257216
SMILES: c1ccccc1C(=O)OCC23C(O3)C4C(O4)CC2
Level: 1
Mol. Weight: 362.33 g/mol
SMILES: C12C3C(O3)CCC1O2
Level: 0
Mol. Weight: 362.33 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 362.33 g/mol
Inhibitory against the lewis lung carcinoma in mice
Absorption
- Caco-2 (logPapp)
- -5.06
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.51
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.54
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.4
- Plasma Protein Binding
- 22.86
- 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
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 13.61
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.13
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.04
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.21
- 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
- -7.02
- Rat (Acute)
- 4.25
- Rat (Chronic Oral)
- 1.92
- Fathead Minnow
- 4.02
- 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
- 378.53
- Hydration Free Energy
- -6.17
- Log(D) at pH=7.4
- 0.82
- Log(P)
- 1.28
- Log S
- -2.88
- Log(Vapor Pressure)
- -7.26
- Melting Point
- 72.39
- pKa Acid
- 6.07
- pKa Basic
- -1.89
| 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 | 1.0020 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 1.0020 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8845 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8845 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8688 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8688 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8602 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8602 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8364 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8364 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.8133 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.8133 |
| Class B acid phosphatase | Q540U1 | APHA_SALTM | Salmonella typhimurium | 2 | 0.7673 |
| Class B acid phosphatase | Q540U1 | APHA_SALTM | Salmonella typhimurium | 2 | 0.7673 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7623 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7623 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7430 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7430 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7413 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7413 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7356 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7356 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7277 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7277 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7257 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7257 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7235 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7235 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7230 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7230 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7228 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7228 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7225 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7225 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7220 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7220 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7216 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7216 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7204 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7204 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7197 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7197 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7195 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7195 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7192 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7192 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7191 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7191 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7188 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7188 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7169 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7169 |
| Multidrug efflux pump subunit AcrB | P31224 | ACRB_ECOLI | Escherichia coli | 3 | 0.7165 |
| Multidrug efflux pump subunit AcrB | P31224 | ACRB_ECOLI | Escherichia coli | 3 | 0.7165 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 2 | 0.7161 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 2 | 0.7161 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.7134 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.7134 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7134 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7134 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7117 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7117 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 2 | 0.7107 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 2 | 0.7107 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7096 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7096 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7096 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7096 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7091 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7091 |
| Acidic phospholipase A2 3 | P60045 | PA2A3_NAJSG | Naja sagittifera | 2 | 0.7082 |
| Acidic phospholipase A2 3 | P60045 | PA2A3_NAJSG | Naja sagittifera | 2 | 0.7082 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7042 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7042 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7038 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7038 |
| Unconventional myosin-Va | Q02440 | MYO5A_CHICK | Gallus gallus | 2 | 0.7034 |
| Unconventional myosin-Va | Q02440 | MYO5A_CHICK | Gallus gallus | 2 | 0.7034 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7023 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7023 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7010 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 2 | 0.7010 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 2 | 0.7010 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7010 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7007 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7007 |