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ChemSpider ID: |
1387
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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: |
5,12-dihydroxyicosa-6,8,10-trien-14-ynoic acid
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SMILES: |
O=C(O)CCCC(O)C=CC=CC=CC(O)CC#CCCCCC
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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/h7-8,10-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)
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InChIKey: |
PRCVOEPTHWOJMX-UHFFFAOYAV
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LogP: |
ACD/LogP:
3.66
XLogP:
4.00
ALOGPS:
4.54
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# of Rule of 5 Violations: |
0
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ACD/LogD (pH 5.5): |
2.76
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ACD/LogD (pH 7.4): |
0.96
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ACD/BCF (pH 5.5): |
44.7
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ACD/BCF (pH 7.4): |
1
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ACD/KOC (pH 5.5): |
292.45
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ACD/KOC (pH 7.4): |
4.61
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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: |
44.76
Å2
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Index of Refraction: |
1.534
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Molar Refractivity: |
97.43
cm3
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Molar Volume: |
313.2
cm3
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Polarizability: |
38.62
10-24cm3
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Surface Tension: |
46.4
dyne/cm
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Density: |
1.067
g/cm3
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Flash Point: |
301.7
°C
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Enthalpy of Vaporization: |
95.68
kJ/mol
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Boiling Point: |
552
°C at 760 mmHg
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Vapour Pressure: |
1.74E-14
mmHg at 25°C
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Log Octanol-Water Partition Coef (SRC):
Log Kow (KOWWIN v1.67 estimate) = 4.90
Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
Boiling Pt (deg C): 489.79 (Adapted Stein & Brown method)
Melting Pt (deg C): 207.83 (Mean or Weighted MP)
VP(mm Hg,25 deg C): 1.46E-012 (Modified Grain method)
Subcooled liquid VP: 1.26E-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): 1.257
log Kow used: 4.90 (estimated)
no-melting pt equation used
Water Sol Estimate from Fragments:
Wat Sol (v1.01 est) = 53.565 mg/L
ECOSAR Class Program (ECOSAR v0.99h):
Class(es) found:
Surfactants-anionic-acid
Vinyl/Allyl Alcohols-acid
Propargyl Alc-hindered-acid
Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
Bond Method : 3.38E-012 atm-m3/mole
Group Method: Incomplete
Henrys LC [VP/WSol estimate using EPI values]: 5.111E-013 atm-m3/mole
Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
Log Kow used: 4.90 (KowWin est)
Log Kaw used: -9.860 (HenryWin est)
Log Koa (KOAWIN v1.10 estimate): 14.760
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) : 0.5521
Biowin6 (MITI Non-Linear Model): 0.3636
Anaerobic Biodegradation Probability:
Biowin7 (Anaerobic Linear Model): 0.3262
Ready Biodegradability Prediction: YES
Hydrocarbon Biodegradation (BioHCwin v1.01):
Structure incompatible with current estimation method!
Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
Vapor pressure (liquid/subcooled): 1.68E-008 Pa (1.26E-010 mm Hg)
Log Koa (Koawin est ): 14.760
Kp (particle/gas partition coef. (m3/ug)):
Mackay model : 179
Octanol/air (Koa) model: 141
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 = 223.2710 E-12 cm3/molecule-sec [Cis-isomer]
OVERALL OH Rate Constant = 229.7310 E-12 cm3/molecule-sec [Trans-isomer]
Half-Life = 0.575 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
Half-Life = 0.559 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
Ozone Reaction:
OVERALL Ozone Rate Constant = 5.836750 E-17 cm3/molecule-sec [Cis-]
OVERALL Ozone Rate Constant = 6.405499 E-17 cm3/molecule-sec [Trans-]
Half-Life = 4.712 Hrs (at 7E11 mol/cm3) [Cis-isomer]
Half-Life = 4.294 Hrs (at 7E11 mol/cm3) [Trans-isomer]
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 = 0.500 (BCF = 3.162)
log Kow used: 4.90 (estimated)
Volatilization from Water:
Henry LC: 3.38E-012 atm-m3/mole (estimated by Bond SAR Method)
Half-Life from Model River: 3.168E+008 hours (1.32E+007 days)
Half-Life from Model Lake : 3.456E+009 hours (1.44E+008 days)
Removal In Wastewater Treatment:
Total removal: 74.28 percent
Total biodegradation: 0.65 percent
Total sludge adsorption: 73.63 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 0.114 0.924 1000
Water 21.9 208 1000
Soil 65.5 416 1000
Sediment 12.5 1.87e+003 0
Persistence Time: 339 hr
Descriptors:
0, 0, 0, 1, 0, 0, 0, 3, 0, 0, 2, 4, 19, 0, 2, 8, 0, 2, 1, 0, 6, 0, 0, 0
| Category | Target | PDB Code | LASSO Score |
| Other Enzymes | HMGR, hydroxymethylglutaryl-CoA reductase | 1hw8 | 0.17 |
| Nuclear Hormone Receptors | GR, glucocorticoid receptor | 1m2z | 0.09 |
| Metalloenzymes | ACE, angiotensin-converting enzyme | 1o86 | 0.03 |
| Nuclear Hormone Receptors | PPARg, peroxisome proliferator activated receptor | 1fm9 | 0.02 |
| Kinases | SRC, tyrosine kinase SRC | 2src | 0.01 |
| Serine Proteases | Thrombin | 1ba8 | 0.01 |
| Other Enzymes | HIVPR, HIV protease | 1hpx | 0.01 |
| Kinases | HSP90, human heat shock protein 90 | 1uy6 | 0.01 |
| Other Enzymes | GPB, glycogen phosphorylase | 1a8i | 0.01 |
| Nuclear Hormone Receptors | MR, mineralocorticoid receptor | 2aa2 | 0.01 |
| Other Enzymes | PARP, poly(ADP-ribose) polymerase | 1efy | 0.01 |
| Other Enzymes | PNP, purine nucleoside phosphorylase | 1b8o | 0.01 |
| Folate Enzymes | DHFR, dihydrofolate reductase | 3dfr | 0.00 |
| Other Enzymes | AmpC, AmpC beta-lactamase | 1xgj | 0.00 |
| Nuclear Hormone Receptors | ER, estrogen receptor; agonist | 1l2i | 0.00 |
| Nuclear Hormone Receptors | PR, progesterone receptor | 1sr7 | 0.00 |
| Other Enzymes | NA, neuraminidase | 1a4g | 0.00 |
| Kinases | VEGFr2, vascular endothelial growth factor receptor | 1vr2 | 0.00 |
| Serine Proteases | Trypsin | 1bju | 0.00 |
| Kinases | FGFr1, fibroblast growth factor receptor kinase | 1agw | 0.00 |
| Other Enzymes | InhA, enoyl ACP reductase | 1p44 | 0.00 |
| Other Enzymes | SAHH, S-adenosyl-homocysteine hydrolase | 1a7a | 0.00 |
| Other Enzymes | COX-2, cyclooxygenase-2 | 1cx2 | 0.00 |
| Metalloenzymes | COMT, catechol O-methyltransferase | 1h1d | 0.00 |
| Kinases | CDK2, cyclindependent kinase 2 | 1ckp | 0.00 |
| Kinases | TK, thymidine kinase | 1kim | 0.00 |
| Nuclear Hormone Receptors | AR, androgen receptor | 1xq2 | 0.00 |
| Kinases | P38 MAP, P38 mitogen activated protein | 1kv2 | 0.00 |
| Other Enzymes | AChE, acetylcholinesterase | 1eve | 0.00 |
| Folate Enzymes | GART, glycinamide ribonucleotide transformylase | 1c2t | 0.00 |
| Kinases | PDGFrb, platelet derived growth factor receptor kinase | N/A | 0.00 |
| Metalloenzymes | ADA, adenosine deaminase | 1stw | 0.00 |
| Kinases | EGFr, epidermal growth factor receptor | 1m17 | 0.00 |
| Serine Proteases | FXa, factor Xa | 1f0r | 0.00 |
| Other Enzymes | HIVRT, HIV reverse transcriptase | 1rt1 | 0.00 |
| Nuclear Hormone Receptors | RXRa, retinoic X receptor R | 1mvc | 0.00 |
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