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3,4-,4′,5′-bis-(2,2-dimethylchromano)-2′-hydroxychalcone
- Family: Plantae - Moraceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Prenylated Flavone
Canonical Smiles | O=C(c1cc2CCC(Oc2cc1O)(C)C)/C=C/c1ccc2c(c1)CCC(O2)(C)C |
---|---|
InChI | InChI=1S/C25H28O4/c1-24(2)11-9-17-13-16(6-8-22(17)28-24)5-7-20(26)19-14-18-10-12-25(3,4)29-23(18)15-21(19)27/h5-8,13-15,27H,9-12H2,1-4H3/b7-5+ |
InChIKey | BQMZTQFILQAXNK-FNORWQNLSA-N |
Formula | C25H28O4 |
HBA | 4 |
HBD | 1 |
MW | 392.5 |
Rotatable Bonds | 3 |
TPSA | 55.76 |
LogP | 5.5 |
Number Rings | 4 |
Number Aromatic Rings | 2 |
Heavy Atom Count | 29 |
Formal Charge | 0 |
Fraction CSP3 | 0.4 |
Exact Mass | 392.2 |
Number of Lipinski Rule Violations | 1 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Dorstenia kameruniana | Moraceae | Plantae | 984812 |
Showing of synonyms
3,4-,4′,5′-bis-(2,2-dimethylchromano)-2′-hydroxychalcone
Bis(6'',6''-dimethyl-4'',5''-dihydropyrano)[2'',3'':4',5'][2'',3'':4,3]-2'-hydroxychalcone
Bis(6'',6''-dimethyl-4'',5''-dihydropyrano)(2'',3'':4',5')(2'',3'':4,3)-2'-hydroxychalcone
(E)-3-(2,2-dimethyl-3,4-dihydrochromen-6-yl)-1-(7-hydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)prop-2-en-1-one
216753-67-2
LMPK12120094
- Abegaz BM, Ngadjui BT, et al. (1998). Prenylated chalcones and flavones from the leaves of dorstenia kameruniana. Phytochemistry, 1998, 49(4), 1147-1150. [View]
No compound-protein relationship available.
SMILES: C1CCOc(c12)ccc(c2)C(=O)C=Cc(c3)ccc(c34)OCCC4
Level: 1
Mol. Weight: 392.5 g/mol
SMILES: C1CCOc(c12)cccc2
Level: 0
Mol. Weight: 392.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.06
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.48
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.11
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.43
- Plasma Protein Binding
- 76.91
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.37
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.66
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.53
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.06
- 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
- Toxic
- T. Pyriformis
- -8.83
- Rat (Acute)
- 2.18
- Rat (Chronic Oral)
- 2.15
- Fathead Minnow
- 5.08
- 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
- 463.66
- Hydration Free Energy
- -6.65
- Log(D) at pH=7.4
- 4.82
- Log(P)
- 7.1
- Log S
- -6.39
- Log(Vapor Pressure)
- -8.14
- Melting Point
- 173.39
- pKa Acid
- 9.7
- pKa Basic
- 6.19
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.9318 |
Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.9317 |
Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.9198 |
Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.9196 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9109 |
Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.9098 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9097 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9084 |
Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.9079 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8926 |
Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 3 | 0.8922 |
Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8890 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8870 |
Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.8867 |
3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8813 |
Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8806 |
NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.8783 |
Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8775 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8771 |
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.8761 |
Nicotinamide phosphoribosyltransferase | P43490 | NAMPT_HUMAN | Homo sapiens | 3 | 0.8754 |
Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8568 |
Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8552 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8549 |
Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8508 |
Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.8461 |
Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.8427 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8388 |
Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.8360 |
CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8353 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8316 |
Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8312 |
cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.8247 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.8237 |
3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.8231 |
Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.8228 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8204 |
Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.8178 |
Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8156 |
Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8129 |
Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.8009 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7994 |
Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7942 |
Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7909 |
Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7908 |
17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7898 |
17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7878 |
Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.7872 |
Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7870 |
17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7848 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7827 |
Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7826 |
Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7822 |
CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7811 |
Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7810 |
Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7791 |
Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.7757 |
Acetylcholine-binding protein | P58154 | ACHP_LYMST | Lymnaea stagnalis | 3 | 0.7744 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7736 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7730 |
Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7718 |
Beta-glucuronidase | P05804 | BGLR_ECOLI | Escherichia coli | 3 | 0.7703 |
Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7682 |
Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7670 |
Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7664 |
Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7658 |
Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7631 |
Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7630 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7605 |
Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7596 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7585 |
Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7565 |
Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.7536 |
Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7531 |
Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 2 | 0.7531 |
Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7495 |
Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7493 |
Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7481 |
Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7474 |
Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7473 |
Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7464 |
Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7451 |
Metapyrocatechase | Q7WYF5 | Q7WYF5_9PSED | Pseudomonas alkylphenolica | 3 | 0.7451 |
L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7448 |
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B | Q13370 | PDE3B_HUMAN | Homo sapiens | 4 | 0.7443 |
Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7439 |
Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.7431 |
Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7429 |
Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7420 |
Aldo-keto reductase family 1 member A1 | P50578 | AK1A1_PIG | Sus scrofa | 3 | 0.7389 |
Cholesterol oxidase | P22637 | CHOD_BREST | Brevibacterium sterolicum | 3 | 0.7373 |
Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7370 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7361 |
Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7346 |
Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7325 |
Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.7323 |
Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 2 | 0.7297 |
Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7292 |
Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7271 |
Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 2 | 0.7256 |
Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7255 |
Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7253 |
Acyl-coenzyme A synthetase ACSM2A, mitochondrial | Q08AH3 | ACS2A_HUMAN | Homo sapiens | 2 | 0.7238 |
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7236 |
NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 2 | 0.7230 |
ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7207 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7200 |
Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7189 |
Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.7182 |
Lanosterol 14-alpha demethylase CYP51 | P10614 | CP51_YEAST | Saccharomyces cerevisiae | 3 | 0.7168 |
Gibberellin receptor GID1A | Q9MAA7 | GID1A_ARATH | Arabidopsis thaliana | 3 | 0.7153 |
Bifunctional protein GlmU | P43889 | GLMU_HAEIN | Haemophilus influenzae | 4 | 0.7152 |
Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7151 |
Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7150 |
Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7144 |
Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 3 | 0.7142 |
Sepiapterin reductase | Q64105 | SPRE_MOUSE | Mus musculus | 3 | 0.7135 |
Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7128 |
Beta-2-microglobulin | P61769 | B2MG_HUMAN | Homo sapiens | 3 | 0.7125 |
cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7124 |
Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 3 | 0.7124 |
Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7123 |
Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7120 |
2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7119 |
NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7115 |
Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7110 |
Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7109 |
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7104 |
Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7081 |
Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7066 |
Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7062 |
Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7061 |
Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7061 |
Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7055 |
Odorant binding protein ASP1 | Q8WRW5 | Q8WRW5_APIME | Apis mellifera | 2 | 0.7034 |
Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7008 |
Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7001 |