Bisdemethoxycurcumin

Details

• Internal ID: 2f147e24-fe43-401b-9077-369fd536bbe5
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
• IUPAC Name: (1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O
• InChI: InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
• InChI Key: PREBVFJICNPEKM-YDWXAUTNSA-N
• Popularity: 259 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₆O₄
• Molecular Weight: 308.30 g/mol
• Exact Mass: 308.10485899 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 33171-05-0
• 24939-16-0
• Curcumin III
• Didemethoxycurcumin
• (1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• Bis(4-hydroxycinnamoyl)methane
• Bis-demethoxycurcumin
• Bisdemethoxycucurmin
• bisdesmethoxycurcumin
• Bis(p-hydroxycinnamoyl)methane
• (E,E)-Bisdemethoxycurcumin
• 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-
• BHCMT
• NSC687839
• UNII-2EFO1BP34R
• 2EFO1BP34R
• 1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
• CHEMBL105350
• CHEBI:71045
• 1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
• 22608-12-4
• 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (1E,6E)-
• p,p'-Dihydroxydicinnamoylmethane
• Curcumin III;Didemethoxycurcumin
• Curcumin Lll
• Curcuminoid A
• Bisdemethoxy Curcumin
• di-p-coumaroylmethane
• Dide Methoxycurcu Min
• INS NO.100(III)
• SCHEMBL428638
• INS-100(III)
• SCHEMBL13521971
• cid_5324473
• HY-N0007A
• DTXSID00872663
• E-100(III)
• (1E,6E)-1,7-Bis(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione
• ZAA93916
• 1,3-Di(4-hydroxystyryl)propanedial
• BIS-DEMETHOXYCURCUMIN [INCI]
• BDBM50059989
• MFCD03419284
• BISDESMETHOXYCURCUMIN [USP-RS]
• AKOS015902102
• CCG-207959
• CCG-208635
• NSC-687839
• Bisdemethoxycurcumin, analytical standard
• AC-24239
• AC-34720
• ADAMANTAN-1-YL-ACETICACIDHYDRAZIDE
• AS-57295
• AS-68737
• B3347
• Bisdemethoxycurcumin, >=98% (HPLC), solid
• CS-0018287
• S3938
• A14544
• A875406
• Q-100322
• Q4917168
• BRD-K37445107-001-01-9
• 1,7-bis(4-hydroxyphenyl)-1,6-Heptadiene-3,5-dione(E,E)
• (1E,6E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
• 1,7-bis(4-hydroxyphenyl)-3-hydroxy-1,3,6-heptatrien-5-one
• 1,7-BIS-(4-HYDROXYPHENYL)-HEPTA-1,6-DIENE-3,5-DIONE
• (1E,6E)-1,7-Bis-(4-hydroxy-phenyl)-hepta-1,6-diene-3,5-dione
• 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (E,E)-
• 5-Hydroxy-1,7-bis-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one
• (1E,4Z,6E)-5-Hydroxy-1,7-bis-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9839	98.39%
Caco-2	-	0.7280	72.80%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8607	86.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9379	93.79%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4508	45.08%
P-glycoprotein inhibitior	-	0.8850	88.50%
P-glycoprotein substrate	-	0.9626	96.26%
CYP3A4 substrate	-	0.7322	73.22%
CYP2C9 substrate	-	0.6056	60.56%
CYP2D6 substrate	-	0.7881	78.81%
CYP3A4 inhibition	+	0.6661	66.61%
CYP2C9 inhibition	+	0.5354	53.54%
CYP2C19 inhibition	+	0.6365	63.65%
CYP2D6 inhibition	-	0.8354	83.54%
CYP1A2 inhibition	+	0.5302	53.02%
CYP2C8 inhibition	-	0.6851	68.51%
CYP inhibitory promiscuity	-	0.5369	53.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6383	63.83%
Carcinogenicity (trinary)	Non-required	0.5765	57.65%
Eye corrosion	-	0.9772	97.72%
Eye irritation	+	0.8400	84.00%
Skin irritation	-	0.6184	61.84%
Skin corrosion	-	0.9599	95.99%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5708	57.08%
Micronuclear	+	0.6659	66.59%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.6181	61.81%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	+	0.5272	52.72%
Acute Oral Toxicity (c)	III	0.6484	64.84%
Estrogen receptor binding	+	0.8680	86.80%
Androgen receptor binding	+	0.6313	63.13%
Thyroid receptor binding	+	0.5204	52.04%
Glucocorticoid receptor binding	+	0.7459	74.59%
Aromatase binding	+	0.7786	77.86%
PPAR gamma	+	0.7720	77.20%
Honey bee toxicity	-	0.9567	95.67%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9743	97.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	60 nM	IC50	via Super-PRED
CHEMBL4147	Q9UQM7	CaM kinase II alpha	37000 nM	IC50	PMID: 22989913
CHEMBL230	P35354	Cyclooxygenase-2	36370 nM	IC50	PMID: 15780608
CHEMBL2424	Q04760	Glyoxalase I	18000 nM; 18200 nM	Ki; Ki	PMID: 21237663; PMID: 21689932

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.99%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.30%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.46%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.63%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.09%	86.33%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.52%	89.67%
CHEMBL4208	P20618	Proteasome component C5	81.40%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.24%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.17%	96.09%

Plants that contains it

• Adiantum capillus-veneris
• Alpinia galanga
• Curcuma chuanyujin
• Curcuma kwangsiensis
• Curcuma longa
• Curcuma mangga
• Curcuma phaeocaulis
• Curcuma wenyujin
• Curcuma zedoaria
• Fraxinus quadrangulata
• Goniothalamus borneensis
• Jacobaea maritima

Cross-Links

• PubChem: 5315472
• NPASS: NPC68269
• ChEMBL: CHEMBL105350
• LOTUS: LTS0068999
• wikiData: Q4917168