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Knipholone-1,3-oxazine
- Family: Plantae - Asphodelaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone
| Canonical Smiles | COc1c2CN(COc2c(c(c1C(=O)C)O)c1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)O)O)c1ccccc1 |
|---|---|
| InChI | InChI=1S/C32H25NO8/c1-15-12-21(36)25-26(28(37)18-10-7-11-20(35)24(18)30(25)39)22(15)27-29(38)23(16(2)34)31(40-3)19-13-33(14-41-32(19)27)17-8-5-4-6-9-17/h4-12,35-36,38H,13-14H2,1-3H3 |
| InChIKey | NGFIYFNVVARSGO-UHFFFAOYSA-N |
| Formula | C32H25NO8 |
| HBA | 9 |
| HBD | 3 |
| MW | 551.55 |
| Rotatable Bonds | 4 |
| TPSA | 133.6 |
| LogP | 5.12 |
| Number Rings | 6 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.16 |
| Exact Mass | 551.16 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bulbine frutescens | Asphodelaceae | Plantae | 210954 |
Showing of synonyms
Knipholone-1,3-oxazine
No compound-protein relationship available.
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4cccc(c45)CN(CO5)c6ccccc6
Level: 2
Mol. Weight: 551.55 g/mol
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4cccc(c45)CNCO5
Level: 1
Mol. Weight: 551.55 g/mol
SMILES: c1cccc(c12)OCN(C2)c3ccccc3
Level: 1
Mol. Weight: 551.55 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 551.55 g/mol
SMILES: C1NCOc(c12)cccc2
Level: 0
Mol. Weight: 551.55 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 551.55 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.43
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.66
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 4.81
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.38
- Plasma Protein Binding
- 86.68
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.31
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.14
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.03
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.63
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- -9562.38
- Rat (Acute)
- 2.51
- Rat (Chronic Oral)
- 2.92
- Fathead Minnow
- 28.5
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 485.06
- Hydration Free Energy
- -2.93
- Log(D) at pH=7.4
- 3.72
- Log(P)
- 5.89
- Log S
- -8.44
- Log(Vapor Pressure)
- -13.26
- Melting Point
- 225.92
- pKa Acid
- 6.31
- pKa Basic
- 3.34
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.9041 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.9041 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.9030 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.9030 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8979 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8979 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8935 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8935 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 4 | 0.8756 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 4 | 0.8756 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 3 | 0.8659 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 3 | 0.8659 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.8622 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.8622 |
| Orf1ab polyprotein | Q6T1E9 | Q6T1E9_CVHSA | SARS coronavirus CUHK-L2 | 4 | 0.8301 |
| Orf1ab polyprotein | Q6T1E9 | Q6T1E9_CVHSA | SARS coronavirus CUHK-L2 | 4 | 0.8301 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.8039 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.8039 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7979 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7979 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7863 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7863 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7827 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7827 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7818 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7818 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7650 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7650 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7627 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7627 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7563 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7563 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7547 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7547 |
| Tyrosine-protein kinase SYK | P43405 | KSYK_HUMAN | Homo sapiens | 4 | 0.7541 |
| Tyrosine-protein kinase SYK | P43405 | KSYK_HUMAN | Homo sapiens | 4 | 0.7541 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7538 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7538 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7520 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7520 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7517 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7517 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7509 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7509 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.7501 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.7501 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7491 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7491 |
| Tau-tubulin kinase 1 | Q5TCY1 | TTBK1_HUMAN | Homo sapiens | 3 | 0.7422 |
| Tau-tubulin kinase 1 | Q5TCY1 | TTBK1_HUMAN | Homo sapiens | 3 | 0.7422 |
| Tryptase alpha/beta-1 | Q15661 | TRYB1_HUMAN | Homo sapiens | 3 | 0.7419 |
| Tryptase alpha/beta-1 | Q15661 | TRYB1_HUMAN | Homo sapiens | 3 | 0.7419 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 4 | 0.7415 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 4 | 0.7415 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7413 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7413 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7385 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7385 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7378 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7378 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7359 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7359 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.7305 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.7305 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7274 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7274 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 3 | 0.7254 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 3 | 0.7254 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7217 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7217 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7213 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7213 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7183 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7183 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7147 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7147 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7132 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7132 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7126 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7126 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7112 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7112 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7111 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7111 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7079 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7079 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7074 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7074 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7056 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7056 |
| Heat shock cognate 71 kDa protein | P11142 | HSP7C_HUMAN | Homo sapiens | 3 | 0.7042 |
| Heat shock cognate 71 kDa protein | P11142 | HSP7C_HUMAN | Homo sapiens | 3 | 0.7042 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 2 | 0.7041 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 2 | 0.7041 |
| Glycoside Hydrolase Family 13 | Q65MI2 | Q65MI2_BACLD | Bacillus licheniformis | 2 | 0.7040 |
| Glycoside Hydrolase Family 13 | Q65MI2 | Q65MI2_BACLD | Bacillus licheniformis | 2 | 0.7040 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 4 | 0.7027 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 4 | 0.7027 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 4 | 0.7000 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 4 | 0.7000 |