InChI=1/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-

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Search term: ZIUSSTSXXLLKKK-KOBPDPAPBH
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Inherent Properties, Identifiers and References

ChemSpider ID:	4445080
Empirical Formula:	C₂₁H₂₀O₆
Molecular Weight:	368.3799
Nominal Mass:	368 Da
Average Mass:	368.3799 Da
Monoisotopic Mass:	368.125988 Da

Systematic Name:

(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,4,6-trien-3-one

SMILES:

O=C(\C=C(/O)\C=C\c1ccc(O)c(OC)c1)\C=C\c2cc(OC)c(O)cc2

InChI:

InChI=1/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-

InChIKey:

ZIUSSTSXXLLKKK-KOBPDPAPBH

Std. 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-

Std. InChIKey:

ZIUSSTSXXLLKKK-KOBPDPAPSA-N

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Wikipedia Article(s)

right|frame|Curcumin Keto form right|frame|Curcumin Enol form Curcumin is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family (Zingiberaceae). The other two curcuminoids are desmethoxycurcumin and bis-desmethoxycurcumin. The curcuminoids are polyphenols and are responsible for the yellow color of turmeric. Curcumin can exist in at least two tautomeric forms, keto and enol. The enol form is more energetically stable in the solid phase and in solution. Curcumin can be used for boron quantification in the so-called curcumin method. It reacts with boric acid forming a red colored compound, known as rosocyanine. Curcumin is brightly colored and may be used as a food coloring. As a food additive, its E number is E100 . Read more... or Edit at Wikipedia...

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miscellaneous

Source: Curcuma spp

No description available

Drug Status: experimental

No description available

Chemical Class: aromatic

No description available

Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

Curcumin (Tautomeric form) [REDIRECT]

(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one

1,4,6-heptatrien-3-one, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-, (1E,4Z,6E)-

(1E,4Z,6E)-5-Hydroxy-1,7-bis-(4-hydroxy-3-methoxy-phenyl)-hepta-1,4,6-trien-3-one

458-37-7 [RN]

Kacha haldi

Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

ACD/Labs Predicted Properties

ACD/LogP:	2.85	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	2.85	ACD/LogD (pH 7.4):	2.79
ACD/BCF (pH 5.5):	86.12	ACD/BCF (pH 7.4):	75.89
ACD/KOC (pH 5.5):	844.42	ACD/KOC (pH 7.4):	744.04
#H bond acceptors:	6	#H bond donors:	3
#Freely Rotating Bonds:	10	Polar Surface Area:	63.22 Å²
Index of Refraction:	1.671	Molar Refractivity:	105.45 cm³
Molar Volume:	281.6 cm³	Polarizability:	41.8 10^-24cm³
Surface Tension:	57.7 dyne/cm	Density:	1.307 g/cm³
Flash Point:	209.7 °C	Enthalpy of Vaporization:	93.02 kJ/mol
Boiling Point:	593.2 °C at 760 mmHg	Vapour Pressure:	6.43E-15 mmHg at 25°C

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  2.59

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  551.06  (Adapted Stein & Brown method)
    Melting Pt (deg C):  236.45  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.61E-014  (Modified Grain method)
    Subcooled liquid VP: 4.99E-012 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  29.27
       log Kow used: 2.59 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  7.2521 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols
       Vinyl/Allyl Ketones
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.84E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.322E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.59  (KowWin est)
  Log Kaw used:  -19.804  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  22.394
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2332
   Biowin2 (Non-Linear Model)     :   0.9915
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.5191  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6571  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4950
   Biowin6 (MITI Non-Linear Model):   0.1484
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0049
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  6.65E-010 Pa (4.99E-012 mm Hg)
  Log Koa (Koawin est  ): 22.394
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.51E+003 
       Octanol/air (Koa) model:  6.08E+009 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 142.5255 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 145.1855 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.901 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.884 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    10.770000 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    11.820000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =     2.554 Hrs (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     2.327 Hrs (at 7E11 mol/cm3) [Trans-isomer]
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2762
      Log Koc:  3.441 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.296 (BCF = 19.78)
       log Kow used: 2.59 (estimated)

 Volatilization from Water:
    Henry LC:  3.84E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.926E+018  hours   (1.219E+017 days)
    Half-Life from Model Lake : 3.192E+019  hours   (1.33E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               3.38  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     3.27  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       8.72e-010       1.06         1000       
   Water     15.2            900          1000       
   Soil      84.6            1.8e+003     1000       
   Sediment  0.148           8.1e+003     0          
     Persistence Time: 1.68e+003 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 6, 0, 0, 3, 6, 0, 6, 6, 5, 12, 0, 1, 1, 6, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.02
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.02
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.02
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Kinases	HSP90, human heat shock protein 90	1uy6	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.01
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Serine Proteases	Trypsin	1bju	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Serine Proteases	Thrombin	1ba8	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00