(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
| Internal ID | 1eb2ba8f-1377-4b33-ac30-ca43dc09e785 |
| Taxonomy | Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids |
| IUPAC Name | (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one |
| SMILES (Canonical) | COC1=C(C=CC(=C1)C=CC(=CC(=O)C=CC2=CC(=C(C=C2)O)OC)O)O |
| SMILES (Isomeric) | COC1=C(C=CC(=C1)/C=C/C(=C/C(=O)/C=C/C2=CC(=C(C=C2)O)OC)/O)O |
| InChI | InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-13,22,24-25H,1-2H3/b7-3+,8-4+,16-13- |
| InChI Key | ZIUSSTSXXLLKKK-KOBPDPAPSA-N |
| Popularity | 64 references in papers |
| Molecular Formula | C21H20O6 |
| Molecular Weight | 368.40 g/mol |
| Exact Mass | 368.12598835 g/mol |
| Topological Polar Surface Area (TPSA) | 96.20 Ų |
| XlogP | 4.00 |
| Atomic LogP (AlogP) | 3.85 |
| H-Bond Acceptor | 6 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 7 |
| CURCUMIN PE |
| BSPBio_003590 |
| MLS002473126 |
| SCHEMBL242412 |
| SCHEMBL23884897 |
| (1E,6E)-1,7-Bis(3-methoxy-4-hydroxyphenyl)-5-hydroxy-1,4,6-heptatriene-3-one |
| REGID_for_CID_5281767 |
| ZIUSSTSXXLLKKK-KOBPDPAPSA-N |
| BDBM191758 |
| HMS3884M12 |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9921 | 99.21% |
| Caco-2 | - | 0.6440 | 64.40% |
| Blood Brain Barrier | - | 0.6250 | 62.50% |
| Human oral bioavailability | + | 0.5286 | 52.86% |
| Subcellular localzation | Mitochondria | 0.8299 | 82.99% |
| OATP2B1 inhibitior | - | 0.5723 | 57.23% |
| OATP1B1 inhibitior | + | 0.9427 | 94.27% |
| OATP1B3 inhibitior | + | 0.9734 | 97.34% |
| MATE1 inhibitior | - | 0.8800 | 88.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | + | 0.9148 | 91.48% |
| P-glycoprotein inhibitior | + | 0.6444 | 64.44% |
| P-glycoprotein substrate | - | 0.9568 | 95.68% |
| CYP3A4 substrate | - | 0.6054 | 60.54% |
| CYP2C9 substrate | - | 0.8088 | 80.88% |
| CYP2D6 substrate | - | 0.8404 | 84.04% |
| CYP3A4 inhibition | - | 0.6550 | 65.50% |
| CYP2C9 inhibition | - | 0.5569 | 55.69% |
| CYP2C19 inhibition | + | 0.8859 | 88.59% |
| CYP2D6 inhibition | - | 0.8180 | 81.80% |
| CYP1A2 inhibition | + | 0.9181 | 91.81% |
| CYP2C8 inhibition | + | 0.6665 | 66.65% |
| CYP inhibitory promiscuity | + | 0.8262 | 82.62% |
| UGT catelyzed | - | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.7525 | 75.25% |
| Carcinogenicity (trinary) | Non-required | 0.6289 | 62.89% |
| Eye corrosion | - | 0.9675 | 96.75% |
| Eye irritation | + | 0.9629 | 96.29% |
| Skin irritation | - | 0.6529 | 65.29% |
| Skin corrosion | - | 0.9576 | 95.76% |
| Ames mutagenesis | - | 0.9100 | 91.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4129 | 41.29% |
| Micronuclear | + | 0.7300 | 73.00% |
| Hepatotoxicity | - | 0.6928 | 69.28% |
| skin sensitisation | - | 0.6927 | 69.27% |
| Respiratory toxicity | - | 0.8333 | 83.33% |
| Reproductive toxicity | + | 0.7778 | 77.78% |
| Mitochondrial toxicity | - | 0.8000 | 80.00% |
| Nephrotoxicity | - | 0.8116 | 81.16% |
| Acute Oral Toxicity (c) | III | 0.5180 | 51.80% |
| Estrogen receptor binding | + | 0.8437 | 84.37% |
| Androgen receptor binding | + | 0.8486 | 84.86% |
| Thyroid receptor binding | + | 0.8355 | 83.55% |
| Glucocorticoid receptor binding | + | 0.8896 | 88.96% |
| Aromatase binding | + | 0.7952 | 79.52% |
| PPAR gamma | + | 0.8087 | 80.87% |
| Honey bee toxicity | - | 0.9382 | 93.82% |
| Biodegradation | - | 0.8750 | 87.50% |
| Crustacea aquatic toxicity | - | 0.6055 | 60.55% |
| Fish aquatic toxicity | + | 0.9888 | 98.88% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL4235 | P28845 | 11-beta-hydroxysteroid dehydrogenase 1 |
15983 nM 4501 nM |
IC50 IC50 |
PMID: 23800686
PMID: 23800686 |
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
22387.2 nM |
Potency |
via CMAUP
|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
19952.6 nM |
Potency |
via CMAUP
|
| CHEMBL1907 | P15144 | Aminopeptidase N |
10000 nM |
IC50 |
PMID: 23860593
|
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
1200 nM |
IC50 |
PMID: 24920381
|
| CHEMBL215 | P09917 | Arachidonate 5-lipoxygenase |
500 nM 500 nM 600 nM 600 nM 600 nM |
IC50 IC50 IC50 IC50 IC50 |
via Super-PRED
PMID: 24920381 PMID: 24920381 PMID: 24920381 PMID: 24920381 |
| CHEMBL2487 | P05067 | Beta amyloid A4 protein |
20300 nM 11000 nM 800 nM 800 nM 12350 nM 0.208 nM 3900 nM |
IC50 IC50 IC50 IC50 IC50 Ki IC50 |
PMID: 24095756
PMID: 25088549 PMID: 18793854 PMID: 17270435 PMID: 23799643 via Super-PRED PMID: 26099993 |
| CHEMBL4822 | P56817 | Beta-secretase 1 |
5300 nM 5700 nM |
IC50 IC50 |
PMID: 25088549
PMID: 23041347 |
| CHEMBL4147 | Q9UQM7 | CaM kinase II alpha |
33000 nM 34000 nM 13000 nM 21000 nM 45000 nM |
IC50 IC50 IC50 IC50 IC50 |
PMID: 22989913
PMID: 22989913 PMID: 22989913 PMID: 22989913 PMID: 22989913 |
| CHEMBL261 | P00915 | Carbonic anhydrase I |
2410 nM |
Ki |
PMID: 20674354
|
| CHEMBL205 | P00918 | Carbonic anhydrase II |
380 nM 380 nM |
Ki Ki |
via Super-PRED
PMID: 20674354 |
| CHEMBL2885 | P07451 | Carbonic anhydrase III |
11300 nM |
Ki |
PMID: 20674354
|
| CHEMBL3729 | P22748 | Carbonic anhydrase IV |
4970 nM |
Ki |
PMID: 20674354
|
| CHEMBL3594 | Q16790 | Carbonic anhydrase IX |
4050 nM |
Ki |
PMID: 20674354
|
| CHEMBL4789 | P35218 | Carbonic anhydrase VA |
10250 nM |
Ki |
PMID: 20674354
|
| CHEMBL3969 | Q9Y2D0 | Carbonic anhydrase VB |
9460 nM |
Ki |
PMID: 20674354
|
| CHEMBL3025 | P23280 | Carbonic anhydrase VI |
9940 nM |
Ki |
PMID: 20674354
|
| CHEMBL2326 | P43166 | Carbonic anhydrase VII |
9300 nM |
Ki |
PMID: 20674354
|
| CHEMBL3242 | O43570 | Carbonic anhydrase XII |
3480 nM |
Ki |
PMID: 20674354
|
| CHEMBL3912 | Q8N1Q1 | Carbonic anhydrase XIII |
6850 nM |
Ki |
PMID: 20674354
|
| CHEMBL3510 | Q9ULX7 | Carbonic anhydrase XIV |
11730 nM |
Ki |
PMID: 20674354
|
| CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
15848.9 nM |
Potency |
via CMAUP
|
| CHEMBL4081 | P13726 | Coagulation factor III |
199.63 nM 199.63 nM 199.63 nM |
IC50 IC50 IC50 |
DOI: 10.1007/s00044-012-0330-5
PMID: 23199480 via Super-PRED |
| CHEMBL221 | P23219 | Cyclooxygenase-1 |
8100 nM 8800 nM 52000 nM 35090 nM |
IC50 IC50 IC50 IC50 |
PMID: 24920381
PMID: 16038536 PMID: 18077363 PMID: 21345672 |
| CHEMBL230 | P35354 | Cyclooxygenase-2 |
11060 nM 79200 nM |
IC50 IC50 |
PMID: 15780608
PMID: 21345672 |
| CHEMBL3356 | P05177 | Cytochrome P450 1A2 |
40000 nM |
IC50 |
PMID: 18249473
|
| CHEMBL4729 | P20813 | Cytochrome P450 2B6 |
24500 nM |
IC50 |
PMID: 18249473
|
| CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
4300 nM |
IC50 |
PMID: 18249473
|
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
16300 nM |
IC50 |
PMID: 18249473
|
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha |
15000 nM |
IC50 |
DOI: 10.1007/s00044-011-9587-3
|
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
25118.9 nM |
Potency |
via CMAUP
|
| CHEMBL203 | P00533 | Epidermal growth factor receptor erbB1 |
8600 nM |
IC50 |
PMID: 23245570
|
| CHEMBL2424 | Q04760 | Glyoxalase I |
10300 nM 10000 nM |
Ki Ki |
PMID: 21689932
PMID: 21237663 |
| CHEMBL4331 | P68871 | Hemoglobin beta chain |
25118.9 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3784 | Q09472 | Histone acetyltransferase p300 |
6500 nM |
IC50 |
PMID: 25730130
|
| CHEMBL1293299 | Q03164 | Histone-lysine N-methyltransferase MLL |
44668.4 nM |
Potency |
via CMAUP
|
| CHEMBL5573 | P09923 | Intestinal alkaline phosphatase |
44100 nM 7410 nM |
IC50 IC50 |
via CMAUP
via CMAUP |
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
19952.6 nM 28183.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
10000 nM |
Potency |
via CMAUP
|
| CHEMBL280 | P45452 | Matrix metalloproteinase 13 |
10300 nM |
IC50 |
PMID: 18358729
|
| CHEMBL321 | P14780 | Matrix metalloproteinase 9 |
8500 nM |
IC50 |
PMID: 19128977
|
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
28183.8 nM 39810.7 nM 7079.5 nM 3162.3 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL4481 | P35228 | Nitric oxide synthase, inducible |
6000 nM |
IC50 |
PMID: 18077363
|
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 |
9900 nM |
EC50 |
PMID: 24920381
|
| CHEMBL5658 | O14684 | Prostaglandin E synthase |
600 nM 1200 nM 600 nM |
IC50 IC50 IC50 |
via Super-PRED
PMID: 24920381 PMID: 24920381 |
| CHEMBL2996 | Q05655 | Protein kinase C delta |
10670 nM |
EC50 |
PMID: 20100661
|
| CHEMBL3582 | Q02156 | Protein kinase C epsilon |
8810 nM |
EC50 |
PMID: 20100661
|
| CHEMBL3920 | Q04759 | Protein kinase C theta |
11080 nM |
EC50 |
PMID: 20100661
|
| CHEMBL4026 | P40763 | Signal transducer and activator of transcription 3 |
19250 nM 19250 nM |
IC50 IC50 |
PMID: 23376248
PMID: 23434226 |
| CHEMBL5804 | Q9NR96 | Toll-like receptor 9 |
15266 nM |
IC50 |
via CMAUP
|
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
5623.4 nM |
Potency |
via CMAUP
|
| CHEMBL1293227 | O75604 | Ubiquitin carboxyl-terminal hydrolase 2 |
10000 nM |
Potency |
via CMAUP
|
| CHEMBL1977 | P11473 | Vitamin D receptor |
20000 nM |
EC50 |
PMID: 23276449
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 96.37% | 91.11% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 95.44% | 86.33% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 95.41% | 96.00% |
| CHEMBL3194 | P02766 | Transthyretin | 94.96% | 90.71% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 93.48% | 95.56% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.47% | 96.09% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 87.61% | 99.17% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 86.19% | 89.00% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 84.89% | 95.50% |
| CHEMBL2085 | P14174 | Macrophage migration inhibitory factor | 83.14% | 80.78% |
| CHEMBL1255126 | O15151 | Protein Mdm4 | 82.70% | 90.20% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 82.13% | 99.15% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.
| PubChem | 5281767 |
| NPASS | NPC109083 |
| ChEMBL | CHEMBL116438 |
| LOTUS | LTS0167680 |
| wikiData | Q76285983 |