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5-hydroxy-6,8,8-trimethyl-2-phenylchromene-4,7-dione
- Family: Plantae - Annonaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavone
| Canonical Smiles | CC1=C(O)c2c(=O)cc(oc2C(C1=O)(C)C)c1ccccc1 |
|---|---|
| InChI | InChI=1S/C18H16O4/c1-10-15(20)14-12(19)9-13(11-7-5-4-6-8-11)22-17(14)18(2,3)16(10)21/h4-9,20H,1-3H3 |
| InChIKey | VOEVEGYLKQKGLZ-UHFFFAOYSA-N |
| Formula | C18H16O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 296.32 |
| Rotatable Bonds | 1 |
| TPSA | 67.51 |
| LogP | 3.46 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.22 |
| Exact Mass | 296.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Uvaria acuminata | Annonaceae | Plantae | 672960 |
Showing of synonyms
5-hydroxy-6,8,8-trimethyl-2-phenylchromene-4,7-dione
Dasytrichone
151655-69-5
Desmotumotin B
C10035
CHEBI:4327
CHEMBL191819
SCHEMBL3545108
SCHEMBL13034005
DTXSID40331880
LMPK12111508
Q27106339
5-hydroxy-6,8,8-trimethyl-2-phenyl-chromene-4,7-dione
Pubchem:
442586
Cas:
151655-69-5
Kegg Ligand:
C10035
Chebi:
4327
Nmrshiftdb2:
70112033
Comptox:
DTXSID40331880
No compound-protein relationship available.
SMILES: C1=CC(=O)Cc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 296.32 g/mol
SMILES: C1=CC(=O)Cc(c12)occc2=O
Level: 0
Mol. Weight: 296.32 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 296.32 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.73
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.36
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.87
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.24
- Plasma Protein Binding
- 56.68
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- 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
- 6.68
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.11
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.14
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.38
- 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
- 3.65
- Rat (Acute)
- 2.6
- Rat (Chronic Oral)
- 1.96
- Fathead Minnow
- 4.55
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 410.47
- Hydration Free Energy
- -11.53
- Log(D) at pH=7.4
- 2.83
- Log(P)
- 3.41
- Log S
- -4.27
- Log(Vapor Pressure)
- -7.23
- Melting Point
- 164.41
- pKa Acid
- 6.42
- pKa Basic
- 4.15
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9555 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9555 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.9459 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.9459 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.9375 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.9375 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.9103 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.9103 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8848 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8848 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8751 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8751 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8514 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8514 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8377 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8377 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.8369 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.8369 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 3 | 0.8259 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 3 | 0.8259 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8231 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8231 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.8166 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.8166 |
| Cytochrome P450 2C9 | P11712 | CP2C9_HUMAN | Homo sapiens | 3 | 0.8004 |
| Cytochrome P450 2C9 | P11712 | CP2C9_HUMAN | Homo sapiens | 3 | 0.8004 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7996 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7996 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7942 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7942 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7940 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7940 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7921 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7921 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7805 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7805 |
| Reductase homolog | Q9ZGC1 | Q9ZGC1_STRCY | Streptomyces cyanogenus | 3 | 0.7793 |
| Reductase homolog | Q9ZGC1 | Q9ZGC1_STRCY | Streptomyces cyanogenus | 3 | 0.7793 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7785 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7785 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 3 | 0.7766 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 3 | 0.7766 |
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 3 | 0.7765 |
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 3 | 0.7765 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7727 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7727 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7709 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7709 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7702 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7702 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7585 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7585 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7580 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7580 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7519 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7519 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7502 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7502 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7478 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7478 |
| cGMP-dependent protein kinase, putative | A5K0N4 | A5K0N4_PLAVS | Plasmodium vivax | 3 | 0.7415 |
| cGMP-dependent protein kinase, putative | A5K0N4 | A5K0N4_PLAVS | Plasmodium vivax | 3 | 0.7415 |
| Egl nine homolog 1 | Q9GZT9 | EGLN1_HUMAN | Homo sapiens | 3 | 0.7411 |
| Egl nine homolog 1 | Q9GZT9 | EGLN1_HUMAN | Homo sapiens | 3 | 0.7411 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 3 | 0.7356 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 3 | 0.7356 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 3 | 0.7343 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 3 | 0.7343 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7337 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7337 |
| Angiopoietin-1 receptor | Q02763 | TIE2_HUMAN | Homo sapiens | 3 | 0.7325 |
| Angiopoietin-1 receptor | Q02763 | TIE2_HUMAN | Homo sapiens | 3 | 0.7325 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7322 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7322 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7303 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7303 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7281 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7281 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7273 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7273 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7234 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7234 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7233 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7233 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 2 | 0.7187 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 2 | 0.7187 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 2 | 0.7169 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 2 | 0.7169 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7153 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7153 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7144 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7144 |
| Aspartate-semialdehyde dehydrogenase | Q51344 | DHAS_PSEAE | Pseudomonas aeruginosa | 3 | 0.7121 |
| Aspartate-semialdehyde dehydrogenase | Q51344 | DHAS_PSEAE | Pseudomonas aeruginosa | 3 | 0.7121 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7095 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7095 |
| Acyl-coenzyme A synthetase ACSM2A, mitochondrial | Q08AH3 | ACS2A_HUMAN | Homo sapiens | 3 | 0.7047 |
| Acyl-coenzyme A synthetase ACSM2A, mitochondrial | Q08AH3 | ACS2A_HUMAN | Homo sapiens | 3 | 0.7047 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7045 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7045 |
| Alpha-aminoadipic semialdehyde dehydrogenase | P49419 | AL7A1_HUMAN | Homo sapiens | 2 | 0.7025 |
| Alpha-aminoadipic semialdehyde dehydrogenase | P49419 | AL7A1_HUMAN | Homo sapiens | 2 | 0.7025 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7020 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7020 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 3 | 0.7016 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 3 | 0.7016 |