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ChemSpider ID: |
20171899
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Empirical Formula: |
C20H30O4
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Molecular Weight: |
334.4498
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Nominal Mass: |
334
Da
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Average Mass: |
334.4498
Da
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Monoisotopic Mass: |
334.214409
Da
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Systematic Name: |
(5S,6Z,8E,10E,12R,14Z,17E)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid
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SMILES: |
O[C@H](/C=C\C=C\C=C\[C@H](O)C/C=C\C\C=C\CC)CCCC(O)=O
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InChI: |
InChI=1/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3+,8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1
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InChIKey: |
BISQPGCQOHLHQK-KDUZLUOGBI
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users,
Redirected by Users, Redirect Approved by Experts
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-6,8,10,14,17-Eicosapentaenoic acid
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LogP: |
ACD/LogP:
3.54
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# of Rule of 5 Violations: |
0
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ACD/LogD (pH 5.5): |
2.64
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ACD/LogD (pH 7.4): |
0.83
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ACD/BCF (pH 5.5): |
35.98
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ACD/BCF (pH 7.4): |
1
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ACD/KOC (pH 5.5): |
250.44
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ACD/KOC (pH 7.4): |
3.95
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#H bond acceptors: |
4
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#H bond donors: |
3
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#Freely Rotating Bonds: |
15
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Polar Surface Area: |
77.76
Å2
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Index of Refraction: |
1.54
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Molar Refractivity: |
99.54
cm3
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Molar Volume: |
317.1
cm3
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Polarizability: |
39.46
10-24cm3
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Surface Tension: |
43.3
dyne/cm
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Density: |
1.054
g/cm3
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Flash Point: |
293.7
°C
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Enthalpy of Vaporization: |
93.83
kJ/mol
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Boiling Point: |
538.7
°C at 760 mmHg
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Vapour Pressure: |
7.47E-14
mmHg at 25°C
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Log Octanol-Water Partition Coef (SRC):
Log Kow (KOWWIN v1.67 estimate) = 5.18
Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
Boiling Pt (deg C): 488.54 (Adapted Stein & Brown method)
Melting Pt (deg C): 191.04 (Mean or Weighted MP)
VP(mm Hg,25 deg C): 2.52E-012 (Modified Grain method)
Subcooled liquid VP: 1.39E-010 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): 0.7171
log Kow used: 5.18 (estimated)
no-melting pt equation used
Water Sol Estimate from Fragments:
Wat Sol (v1.01 est) = 81.353 mg/L
ECOSAR Class Program (ECOSAR v0.99h):
Class(es) found:
Surfactants-anionic-acid
Vinyl/Allyl Alcohols-acid
Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
Bond Method : 4.20E-011 atm-m3/mole
Group Method: Incomplete
Henrys LC [VP/WSol estimate using EPI values]: 1.547E-012 atm-m3/mole
Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
Log Kow used: 5.18 (KowWin est)
Log Kaw used: -8.765 (HenryWin est)
Log Koa (KOAWIN v1.10 estimate): 13.945
Log Koa (experimental database): None
Probability of Rapid Biodegradation (BIOWIN v4.10):
Biowin1 (Linear Model) : 1.0869
Biowin2 (Non-Linear Model) : 0.9517
Expert Survey Biodegradation Results:
Biowin3 (Ultimate Survey Model): 3.4429 (days-weeks )
Biowin4 (Primary Survey Model) : 4.2787 (hours-days )
MITI Biodegradation Probability:
Biowin5 (MITI Linear Model) : 0.4780
Biowin6 (MITI Non-Linear Model): 0.2133
Anaerobic Biodegradation Probability:
Biowin7 (Anaerobic Linear Model): -0.0199
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): 1.85E-008 Pa (1.39E-010 mm Hg)
Log Koa (Koawin est ): 13.945
Kp (particle/gas partition coef. (m3/ug)):
Mackay model : 162
Octanol/air (Koa) model: 21.6
Fraction sorbed to airborne particulates (phi):
Junge-Pankow model : 1
Mackay model : 1
Octanol/air (Koa) model: 0.999
Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
Hydroxyl Radicals Reaction:
OVERALL OH Rate Constant = 305.8152 E-12 cm3/molecule-sec [Cis-isomer]
OVERALL OH Rate Constant = 327.4752 E-12 cm3/molecule-sec [Trans-isomer]
Half-Life = 25.182 Min (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
Half-Life = 23.517 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
Ozone Reaction:
OVERALL Ozone Rate Constant = 31.833750 E-17 cm3/molecule-sec [Cis-]
OVERALL Ozone Rate Constant = 46.402500 E-17 cm3/molecule-sec [Trans-]
Half-Life = 51.839 Min (at 7E11 mol/cm3) [Cis-isomer]
Half-Life = 35.564 Min (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 : 95.29
Log Koc: 1.979
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 = 0.750 (BCF = 5.623)
log Kow used: 5.18 (estimated)
Volatilization from Water:
Henry LC: 4.2E-011 atm-m3/mole (estimated by Bond SAR Method)
Half-Life from Model River: 2.549E+007 hours (1.062E+006 days)
Half-Life from Model Lake : 2.781E+008 hours (1.159E+007 days)
Removal In Wastewater Treatment:
Total removal: 82.65 percent
Total biodegradation: 0.71 percent
Total sludge adsorption: 81.94 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 0.0572 0.426 1000
Water 20.3 208 1000
Soil 58.6 416 1000
Sediment 21 1.87e+003 0
Persistence Time: 348 hr
Descriptors:
0, 0, 0, 1, 0, 0, 0, 3, 0, 0, 2, 4, 15, 0, 2, 10, 0, 2, 1, 0, 10, 0, 0, 0
| Category | Target | PDB Code | LASSO Score |
| Metalloenzymes | ACE, angiotensin-converting enzyme; | 1o86 | 0.03 |
| Other Enzymes | AChE, acetylcholinesterase; | 1eve | 0.00 |
| Metalloenzymes | ADA, adenosine deaminase; | 1stw | 0.00 |
| Other Enzymes | ALR2, aldose reductase; | 1ah3 | 0.00 |
| Other Enzymes | AmpC, AmpC beta-lactamase; | 1xgj | 0.00 |
| Nuclear Hormone Receptors | AR, androgen receptor; | 1xq2 | 0.00 |
| Kinases | CDK2, cyclindependent kinase 2; | 1ckp | 0.00 |
| Metalloenzymes | COMT, catechol O-methyltransferase; | 1h1d | 0.00 |
| Other Enzymes | COX-1, cyclooxygenase-1; | 1p4g | 0.00 |
| Other Enzymes | cyclooxygenase-2 | 1cx2 | 0.00 |
| Folate Enzymes | DHFR, dihydrofolate reductase; | 3dfr | 0.00 |
| Kinases | EGFr, epidermal growth factor receptor; | 1m17 | 0.00 |
| Nuclear Hormone Receptors | ER, estrogen receptor; agonist | 1l2i | 0.00 |
| Nuclear Hormone Receptors | ER, estrogen receptor; antagonist | 3ert | 0.00 |
| Kinases | FGFr1, fibroblast growth factor receptor kinase; | 1agw | 0.00 |
| Serine Proteases | FXa, factor Xa; | 1f0r | 0.00 |
| Folate Enzymes | GART, glycinamide ribonucleotide transformylase; | 1c2t | 0.00 |
| Other Enzymes | GPB, glycogen phosphorylase â; | 1a8i | 0.02 |
| Nuclear Hormone Receptors | GR, glucocorticoid receptor; | 1m2z | 0.10 |
| Other Enzymes | HIVPR, HIV protease; | 1hpx | 0.01 |
| Other Enzymes | HIVRT, HIV reverse transcriptase; | 1rt1 | 0.00 |
| Other Enzymes | HMGR, hydroxymethylglutaryl-CoA reductase; | 1hw8 | 0.39 |
| Kinases | HSP90, human heat shock protein 90; | 1uy6 | 0.01 |
| Other Enzymes | InhA, enoyl ACP reductase; | 1p44 | 0.00 |
| Nuclear Hormone Receptors | MR, mineralocorticoid receptor; | 2aa2 | 0.00 |
| Other Enzymes | NA, neuraminidase; | 1a4g | 0.02 |
| Kinases | P38 MAP, P38 mitogen activated protein; | 1kv2 | 0.00 |
| Other Enzymes | PARP, poly(ADP-ribose) polymerase; | 1efy | 0.01 |
| Metalloenzymes | PDE5, phosphodiesterase 5; | 1xp0 | 0.00 |
| Kinases | PDGFrb, platelet derived growth factor receptor kinase; | | 0.02 |
| Other Enzymes | PNP, purine nucleoside phosphorylase; | 1b8o | 0.01 |
| Nuclear Hormone Receptors | PPARg, peroxisome proliferator activated receptor ç; | 1fm9 | 0.03 |
| Nuclear Hormone Receptors | PR, progesterone receptor; | 1sr7 | 0.00 |
| Nuclear Hormone Receptors | RXRa, retinoic X receptor R; | 1mvc | 0.00 |
| Other Enzymes | SAHH, S-adenosyl-homocysteine hydrolase; | 1a7a | 0.00 |
| Kinases | SRC, tyrosine kinase SRC; | 2src | 0.01 |
| Serine Proteases | Thrombin | 1ba8 | 0.01 |
| Kinases | TK, thymidine kinase; | 1kim | 0.00 |
| Serine Proteases | Trypsin | 1bju | 0.00 |
| Kinases | VEGFr2, vascular endothelial growth factor receptor; | 1vr2 | 0.00 |
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