Demethoxycurcumin

Details

• Internal ID: 1d20ec8b-47ee-4096-bc7f-ffb5caf456f5
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• InChI: InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+
• InChI Key: HJTVQHVGMGKONQ-LUZURFALSA-N
• Popularity: 254 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.36
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• 22608-11-3
• curcumin II
• desmethoxycurcumin
• BHCFM
• Demethoxy Curcumin
• (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• 4-Hydroxycinnamoyl(feroyl)methane
• Feruloyl-P-hydroxycinnnamoylmethane
• demethoxy-curcumin
• CHEBI:65737
• W2F8059T80
• DTXSID00873751
• RefChem:131719
• DTXCID001011975
• (1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
• 663-429-8
• 24939-17-1
• monodemethoxycurcumin
• 33171-16-3
• (2E)-Demethoxy Curcumin
• MFCD03427310
• curcuminII
• (E/Z)-Demethoxycurcumin
• 1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-
• C20H18O5
• 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• (1E,6E)-1-(4-HYDROXY-3-METHOXY-PHENYL)-7-(4-HYDROXYPHENYL)HEPTA-1,6-DI ENE-3,5-DIONE
• CHEMBL105360
• 4-hydroxycinnamoyl(feruloyl)methane
• NSC687841
• (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
• p-Hydroxycinnamoyl-feruloylmethane
• 1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
• (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione
• 1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-, (1E,6E)-
• (1E,6E)-1-(4-HYDROXY-3-METHOXY-PHENYL)-7-(4-HYDROXYPHENYL)HEPTA-1,6-DIENE-3,5-DIONE
• p-Hydroxycinnamoylferuloylmethane
• UNII-W2F8059T80
• Curcumin II;Desmethoxycurcumin;Monodemethoxycurcumin
• feruloyl-p-coumaroylmethane
• Demethoxycurcumin (Standard)
• SCHEMBL431246
• INS NO.100(II)
• orb1300195
• SCHEMBL13521973
• cid_5324476
• HY-N0006A
• HY-N0006R
• INS-100(II)
• HJTVQHVGMGKONQ-LUZURFALSA-N
• DESMETHOXYCURCUMIN [USP-RS]
• 297160-27-1
• MSK40221
• ZINC5115722
• Demethoxycurcumin, >=98% (HPLC)
• 9331AF
• BDBM50163744
• BDBM50410873
• E-100(II)
• s9280
• Demethoxycurcumin, analytical standard
• AKOS015903509
• CCG-267896
• FD20982
• FD73796
• NSC-687841
• (E,E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
• AC-34584
• BS-48948
• DA-52433
• LS-14764
• SY074304
• CS-0009120
• NS00116352
• Q5264607
• I14-18646
• (1E,6E)-1-(4-Hydroxy-3-methoxy-phenyl)-7-(4-hydroxy-phenyl)-hepta-1,6-diene-3,5-dione
• 1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)- (VAN)
• 1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9CI
• 1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-hepta-1,6-diene-3,5-dione
• 5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
• (1E,4Z,6E)-5-Hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one
• (1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione;(1E,6E)-1-(4-Hydroxyphenyl)-7-(4-hydroxy-3-methox yphenyl)-1,6-heptadiene-3,5-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9810	98.10%
Caco-2	-	0.7883	78.83%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8228	82.28%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9381	93.81%
OATP1B3 inhibitior	+	0.9561	95.61%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7890	78.90%
P-glycoprotein inhibitior	-	0.7265	72.65%
P-glycoprotein substrate	-	0.8875	88.75%
CYP3A4 substrate	-	0.5770	57.70%
CYP2C9 substrate	-	0.6120	61.20%
CYP2D6 substrate	-	0.7654	76.54%
CYP3A4 inhibition	-	0.6654	66.54%
CYP2C9 inhibition	+	0.7864	78.64%
CYP2C19 inhibition	+	0.8365	83.65%
CYP2D6 inhibition	-	0.5346	53.46%
CYP1A2 inhibition	+	0.8959	89.59%
CYP2C8 inhibition	+	0.7993	79.93%
CYP inhibitory promiscuity	+	0.5691	56.91%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7899	78.99%
Carcinogenicity (trinary)	Non-required	0.6580	65.80%
Eye corrosion	-	0.9743	97.43%
Eye irritation	+	0.5507	55.07%
Skin irritation	-	0.7645	76.45%
Skin corrosion	-	0.9204	92.04%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6587	65.87%
Micronuclear	+	0.7277	72.77%
Hepatotoxicity	-	0.9198	91.98%
skin sensitisation	-	0.8082	80.82%
Respiratory toxicity	-	0.8333	83.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.6400	64.00%
Acute Oral Toxicity (c)	III	0.6250	62.50%
Estrogen receptor binding	+	0.8797	87.97%
Androgen receptor binding	+	0.6620	66.20%
Thyroid receptor binding	+	0.6273	62.73%
Glucocorticoid receptor binding	+	0.8605	86.05%
Aromatase binding	+	0.7950	79.50%
PPAR gamma	+	0.8570	85.70%
Honey bee toxicity	-	0.9289	92.89%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9732	97.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.29%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.52%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.47%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.15%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.20%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.07%	95.56%
CHEMBL3194	P02766	Transthyretin	91.04%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.74%	89.62%
CHEMBL4208	P20618	Proteasome component C5	89.69%	90.00%
CHEMBL2535	P11166	Glucose transporter	89.50%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.43%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.10%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	80.37%	90.20%

Plants that contains it

• Adiantum capillus-veneris
• Curcuma aromatica
• Curcuma chuanyujin
• Curcuma kwangsiensis
• Curcuma longa
• Curcuma mangga
• Curcuma phaeocaulis
• Curcuma wenyujin
• Curcuma zedoaria
• Etlingera elatior
• Fraxinus quadrangulata
• Goniothalamus borneensis
• Jacobaea maritima

Cross-Links

• PubChem: 5469424
• NPASS: NPC71941
• LOTUS: LTS0035544
• wikiData: Q5264607