3,4-,4′,5′-bis-(2,2-dimethylchromano)-2′-hydroxychalcone - Compound Card

3,4-,4′,5′-bis-(2,2-dimethylchromano)-2′-hydroxychalcone

Select a section from the left sidebar

3,4-,4′,5′-bis-(2,2-dimethylchromano)-2′-hydroxychalcone

Structure
Zoomed Structure
  • 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

  • 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.

Structure

SMILES: C1CCOc(c12)ccc(c2)C(=O)C=Cc(c3)ccc(c34)OCCC4

Level: 1

Mol. Weight: 392.5 g/mol

Structure

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

Download SDF