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Macluraxanthone
- Family: Plantae - Guttiferae
- Kingdom: Plantae
- Class: Xanthone
| Canonical Smiles | C=CC(c1c2OC(C)(C)C=Cc2c(c2c1oc1c(O)c(O)ccc1c2=O)O)(C)C |
|---|---|
| InChI | InChI=1S/C23H22O6/c1-6-22(2,3)15-19-12(9-10-23(4,5)29-19)17(26)14-16(25)11-7-8-13(24)18(27)20(11)28-21(14)15/h6-10,24,26-27H,1H2,2-5H3 |
| InChIKey | XRVLGJCHUWXTDX-UHFFFAOYSA-N |
| Formula | C23H22O6 |
| HBA | 6 |
| HBD | 3 |
| MW | 394.42 |
| Rotatable Bonds | 2 |
| TPSA | 100.13 |
| LogP | 4.71 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.26 |
| Exact Mass | 394.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Allanblackia floribunda | Guttiferae | Plantae | 469914 |
| 2 | Allanblackia floribunda | Guttiferae | Plantae | 469914 |
Showing of synonyms
Macluraxanthone
5848-14-6
5,9,10-trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)pyrano[3,2-b]xanthen-6-one
NSC 107228
DTXSID40207172
12-(1,1-dimethylallyl)-5,9,10-trihydroxy-2,2-dimethyl-pyrano[3,2-b]xanthen-6-one
2H,6H-Pyrano(3,2-b)xanthen-6-one, 12-(1,1-dimethyl-2-propenyl)-5,9,10-trihydroxy-2,2-dimethyl-
12-(1,1-dimethylallyl)-5,9,10-trihydroxy-2,2-dimethyl-pyrano(3,2-b)xanthen-6-one
5,9,10-trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)pyrano(3,2-b)xanthen-6-one
12-(1,1-Dimethyl-2-propenyl)-5,9,10-trihydroxy-2,2-dimethyl-2H,6H-pyrano(3,2-b)xanthen-6-one
12-(1,1-Dimethyl-2-propenyl)-5,9,10-trihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one
DTXCID40129663
NSC107228
3-Hydroxyblancoxanthone
Spectrum_000523
SpecPlus_000294
CHEBI:6623
MACLUROXANTHONE
Spectrum2_000431
Spectrum3_000165
Spectrum4_001486
Spectrum5_000191
BSPBio_001629
KBioGR_002091
KBioSS_001003
DivK1c_006390
SPBio_000442
CHEMBL478960
SCHEMBL2546452
KBio1_001334
KBio2_001003
KBio2_003571
KBio2_006139
KBio3_001129
GLXC-25150
BDBM50378020
CCG-38685
AKOS027326817
NSC-107228
NCGC00160168-01
NCGC00160168-02
12-(1,1-Dimethylprop-2-en-1-yl)-5,9,10-trihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one
XM161793
NCGC00160168-01!MACLUROXANTHONE
BRD-K08362773-001-02-2
Q27107277
12-(1,1-Dimethyl-2-propenyl)-5,9,10-trihydroxy-2,2-dimethyl-2H,6H- pyrano[3,2-b]xanthen-6-one
12-(1,1-Dimethyl-2-propen-1-yl)-5,9,10-trihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one
- Azebaze AG, Teinkela JE, et al. (2015). Antiplasmodial activity of some phenolic compounds from Cameroonians Allanblackia.. African health sciences,2015, 15(3), 835-840. [View] [PubMed]
- Menasria F, Azebaze AG, et al. (2008). Apoptotic effects on B-cell chronic lymphocytic leukemia (B-CLL) cells of heterocyclic compounds isolated from Guttiferaes.. Leukemia research,2008, 32(12), 1914-1926. [View] [PubMed]
Pubchem:
5281646
Cas:
5848-14-6
Gnps:
CCMSLIB00000078819
Zinc:
ZINC000005447704
Kegg Ligand:
C10076
Chebi:
6623
Nmrshiftdb2:
60030278
Chembl:
CHEMBL478960
Comptox:
DTXSID40207172
Bindingdb:
50378020
CPRiL:
414533
SMILES: O1CC=Cc(c2)c1cc(c23)oc4c(c3=O)cccc4
Level: 0
Mol. Weight: 394.42 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -5.11
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.83
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.57
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.22
- Plasma Protein Binding
- 62.58
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.27
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.96
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.61
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.59
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -6.75
- Rat (Acute)
- 2.53
- Rat (Chronic Oral)
- 2.6
- Fathead Minnow
- 5.07
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 497.9
- Hydration Free Energy
- -7.52
- Log(D) at pH=7.4
- 3.29
- Log(P)
- 5.55
- Log S
- -5.69
- Log(Vapor Pressure)
- -9.17
- Melting Point
- 226.03
- pKa Acid
- 6.84
- pKa Basic
- 5.87
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.9264 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9187 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9152 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8653 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.8633 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8619 |
| TetR family transcriptional regulator | Q58L87 | Q58L87_MYCSM | Mycolicibacterium smegmatis | 3 | 0.8438 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8300 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8054 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.8030 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8024 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.7977 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7968 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7774 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7754 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 4 | 0.7677 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7652 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 4 | 0.7649 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7642 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.7630 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7557 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.7554 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7543 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7541 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.7479 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7466 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7446 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7421 |
| Catalase-peroxidase | Q3JNW6 | KATG_BURP1 | Burkholderia pseudomallei | 3 | 0.7421 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7379 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7377 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7372 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 3 | 0.7317 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7266 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7259 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7248 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7243 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7238 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7168 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7168 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7158 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7138 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7040 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7034 |
| cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B | Q13370 | PDE3B_HUMAN | Homo sapiens | 4 | 0.7027 |