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EC number: 288-470-5 | CAS number: 85736-59-0
Physical & Chemical properties
Partition coefficient
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Administrative data
Link to relevant study record(s)
- Endpoint:
- partition coefficient
- Type of information:
- (Q)SAR
- Adequacy of study:
- key study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- results derived from a valid (Q)SAR model and falling into its applicability domain, with limited documentation / justification
- Justification for type of information:
- 1. SOFTWARE
EPI Suite (US EPA) 4.1
2. MODEL (incl. version number)
KOWWIN v1.68
3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
C(=O)(O)CCCCC
C(=O)(O)CCCCCC
C(=O)(O)CCCCCCC
C(=O)(O)CCC1CCCC1
C(=O)(O)CCCC(C)CCC
C(=O)(O)CCCC(CCC)CC
C(=O)(O)CCC1C(CC)CCC1
C(=O)(O)CCC1C(CCC)CCC1
C(=O)(O)CCC1C(CCC)CCCC1
C(=O)(O)CCC1C(CCCC)CCC1
C(=O)(O)CCC1C2C(C)CCC2CC1
C(=O)(O)CCC1C(C2CCCC2)CCC1
O=C(O)CCC2CCCC1CCC(C)C12
O=C(O)C1C(CCCCCCCC)CCC1
C(=O)(O)CCC1CC(C2C(C)CCC2)CC1
C(=O)(O)CCCC1C2C(CC)CCC2CC1
C(=O)(O)CCCCC(CCCCCC)CCC
C(=O)(O)CCC1C(CC(CCC)CC)CCC1
C(=O)(O)CCC1C(CC2CC(C)CC2)CCC1
O=C(O)CCC1CCC2CCCC(CC)C2C1
C(=O)(O)CCCC1C2C3C(CC2CC1)CCC3C
C(=O)(O)CCC1C(CCCCCCCC)CCC1
C(=O)(O)CCC1CC(C2C(CCC)CCC2)CC1
C(=O)(O)C1C(CCC2C(C)CCCC2)CCCC1
C(=O)(O)CC1C2C(CC3CCCC3)CCC2CC1
C(=O)(O)CCC1C(CCCCCCCCC)CCC1
C12(C3C(CC(=O)O)CCC3CC1)C1C(CCC1)CC2
C(=O)(O)CCC1C(CC(CCCC)CCC)CCCC1
C(=O)(O)CCCCC1C2C(C3CCCC3)CCC2CC1
C(=O)(O)CCCCC1C2C(C(CCC)CC)CCC2CC1
C(=O)(O)CC1CC(CC(CCC2CCCC2)CCC)CC1
C(=O)(O)CCCC(CCC1C(CCC2C(C)CCCC2)CCCC1)CCC
C(=O)(O)CCC(CCCC1C(CCC2C(CCCCCC)CCCC2)CCCC1)CCC
C(=O)(O)CCCCCCC1C(CCC2C(CCCC3CCCCC3)CCCC2)CCCC1
O=C(O)CCCCC(CC)CCC1CC2CCCC3CC(CCC(CC)CC)CC(C1)C23
O=C(O)CCCC(CCC)CCCC1CCC2CC(CCC2C1)CC3CCCC(C)C3
4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
- Defined endpoint:
Partition coefficient (n-Octanol/Water)
- Unambiguous algorithm:
Results of the two successive multiple regressions (first for atom/fragments and second for correction factors) yield the following general equation for estimating log P of any organic compound: log P = Σ(fini ) + Σ(cjnj ) + 0.229 (num = 2447, r2 = 0.982, std dev = 0.217, mean error = 0.159)
- Defined domain of applicability:
Log P estimates are less accurate for compounds outside the MW range (18.02 - 199.98) of the training set compounds, and/or that have more instances of a given fragment than the maximum for all training set compounds.
- Appropriate measures of goodness-of-fit and robustness and predictivity:
R² = 0.94
- Mechanistic interpretation:
KOWWIN uses a "fragment constant" methodology to predict log P. In a "fragment constant" method, a structure is divided into fragments (atom or larger functional groups) and coefficient values of each fragment or group are summed together to yield the log P estimate. KOWWIN’s methodology is known as an Atom/Fragment Contribution (AFC) method. Coefficients for individual fragments and groups were derived by multiple regression of 2447 reliably measured log P values. KOWWIN’s "reductionist" fragment constant methodology (i.e. derivation via multiple regression) differs from the "constructionist" fragment constant methodology of Hansch and Leo (1979) that is available in the CLOGP Program (Daylight, 1995).
5. APPLICABILITY DOMAIN
- Descriptor domain:
Molecular weight = 116 - 448
- Structural and mechanistic domains:
Functional groups are within the domain of the model.
-CH3 (aliphatic carbon) 1 fragment (model maximum: 20)
-CH2- (aliphatic carbon) 2 fragments (model maximum: 28)
-CH (aliphatic carbon) 1 fragment (model maximum: 23)
-COOH (hydroxy, aliphatic attach) 2 fragments (model maximum: 9)
- Similarity with analogues in the training set:
There are close structural analogues (~ 190 organic acids) in the training set.
6. ADEQUACY OF THE RESULT
The prediction is reliable and log Kow is required for risk assessment and classification and labelling purposes.
This endpoint study record is part of a Weight of Evidence approach comprising of QSAR prediction and a literature derived value. The data sources agree as to the partition coefficient value and are sufficient to fulfil the information requirements as further explained in the provided endpoint summary. - Guideline:
- other: REACH Guidance on QSARs R.6
- Principles of method if other than guideline:
- - Software tool(s) used including version: EPI Suite (US EPA) 4.1
- Model(s) used: KOWWIN v1.68 (September 2010)
- Model description: see field 'Justification for type of information'
- Justification of QSAR prediction: see field 'Justification for type of information' - GLP compliance:
- no
- Type of method:
- calculation method (fragments)
- Partition coefficient type:
- octanol-water
- Specific details on test material used for the study:
- SMILES:
C(=O)(O)CCCCC
C(=O)(O)CCCCCC
C(=O)(O)CCCCCCC
C(=O)(O)CCC1CCCC1
C(=O)(O)CCCC(C)CCC
C(=O)(O)CCCC(CCC)CC
C(=O)(O)CCC1C(CC)CCC1
C(=O)(O)CCC1C(CCC)CCC1
C(=O)(O)CCC1C(CCC)CCCC1
C(=O)(O)CCC1C(CCCC)CCC1
C(=O)(O)CCC1C2C(C)CCC2CC1
C(=O)(O)CCC1C(C2CCCC2)CCC1
O=C(O)CCC2CCCC1CCC(C)C12
O=C(O)C1C(CCCCCCCC)CCC1
C(=O)(O)CCC1CC(C2C(C)CCC2)CC1
C(=O)(O)CCCC1C2C(CC)CCC2CC1
C(=O)(O)CCCCC(CCCCCC)CCC
C(=O)(O)CCC1C(CC(CCC)CC)CCC1
C(=O)(O)CCC1C(CC2CC(C)CC2)CCC1
O=C(O)CCC1CCC2CCCC(CC)C2C1
C(=O)(O)CCCC1C2C3C(CC2CC1)CCC3C
C(=O)(O)CCC1C(CCCCCCCC)CCC1
C(=O)(O)CCC1CC(C2C(CCC)CCC2)CC1
C(=O)(O)C1C(CCC2C(C)CCCC2)CCCC1
C(=O)(O)CC1C2C(CC3CCCC3)CCC2CC1
C(=O)(O)CCC1C(CCCCCCCCC)CCC1
C12(C3C(CC(=O)O)CCC3CC1)C1C(CCC1)CC2
C(=O)(O)CCC1C(CC(CCCC)CCC)CCCC1
C(=O)(O)CCCCC1C2C(C3CCCC3)CCC2CC1
C(=O)(O)CCCCC1C2C(C(CCC)CC)CCC2CC1
C(=O)(O)CC1CC(CC(CCC2CCCC2)CCC)CC1
C(=O)(O)CCCC(CCC1C(CCC2C(C)CCCC2)CCCC1)CCC
C(=O)(O)CCC(CCCC1C(CCC2C(CCCCCC)CCCC2)CCCC1)CCC
C(=O)(O)CCCCCCC1C(CCC2C(CCCC3CCCCC3)CCCC2)CCCC1
O=C(O)CCCCC(CC)CCC1CC2CCCC3CC(CCC(CC)CC)CC(C1)C23
O=C(O)CCCC(CCC)CCCC1CCC2CC(CCC2C1)CC3CCCC(C)C3 - Type:
- log Pow
- Partition coefficient:
- -0.29
- Remarks on result:
- not measured/tested
- Type:
- log Pow
- Partition coefficient:
- 2.05
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCCC
- Type:
- log Pow
- Partition coefficient:
- 2.54
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCCCC
- Type:
- log Pow
- Partition coefficient:
- 3.03
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCCCCC
- Type:
- log Pow
- Partition coefficient:
- 2.85
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1CCCC1
- Type:
- log Pow
- Partition coefficient:
- 3.45
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCC(C)CCC
- Type:
- log Pow
- Partition coefficient:
- 3.94
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCC(CCC)CC
- Type:
- log Pow
- Partition coefficient:
- 3.76
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(CC)CCC1
- Type:
- log Pow
- Partition coefficient:
- 4.25
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(CCC)CCC1
- Type:
- log Pow
- Partition coefficient:
- 4.74
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(CCC)CCCC1
- Type:
- log Pow
- Partition coefficient:
- 4.74
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(CCCC)CCC1
- Type:
- log Pow
- Partition coefficient:
- 3.79
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C2C(C)CCC2CC1
- Type:
- log Pow
- Partition coefficient:
- 5.04
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(C2CCCC2)CCC1
- Type:
- log Pow
- Partition coefficient:
- 4.29
- Remarks on result:
- not measured/tested
- Remarks:
- O=C(O)CCC2CCCC1CCC(C)C12
- Type:
- log Pow
- Partition coefficient:
- 5.72
- Remarks on result:
- not measured/tested
- Remarks:
- O=C(O)C1C(CCCCCCCC)CCC1
- Type:
- log Pow
- Partition coefficient:
- 5.46
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1CC(C2C(C)CCC2)CC1
- Type:
- log Pow
- Partition coefficient:
- 4.78
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCC1C2C(CC)CCC2CC1
- Type:
- log Pow
- Partition coefficient:
- 6.4
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCCC(CCCCCC)CCC
- Type:
- log Pow
- Partition coefficient:
- 6.14
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(CC(CCC)CC)CCC1
- Type:
- log Pow
- Partition coefficient:
- 5.95
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(CC2CC(C)CC2)CCC1
- Type:
- log Pow
- Partition coefficient:
- 5.27
- Remarks on result:
- not measured/tested
- Remarks:
- O=C(O)CCC1CCC2CCCC(CC)C2C1
- Type:
- log Pow
- Partition coefficient:
- 4.82
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCC1C2C3C(CC2CC1)CCC3C
- Type:
- log Pow
- Partition coefficient:
- 6.7
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(CCCCCCCC)CCC1
- Type:
- log Pow
- Partition coefficient:
- 6.44
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1CC(C2C(CCC)CCC2)CC1
- Type:
- log Pow
- Partition coefficient:
- 6.44
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)C1C(CCC2C(C)CCCC2)CCCC1
- Type:
- log Pow
- Partition coefficient:
- 5.57
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CC1C2C(CC3CCCC3)CCC2CC1
- Type:
- log Pow
- Partition coefficient:
- 7.19
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(CCCCCCCCC)CCC1
- Type:
- log Pow
- Partition coefficient:
- 5.16
- Remarks on result:
- not measured/tested
- Remarks:
- C12(C3C(CC(=O)O)CCC3CC1)C1C(CCC1)CC2
- Type:
- log Pow
- Partition coefficient:
- 7.61
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC1C(CC(CCCC)CCC)CCCC1
- Type:
- log Pow
- Partition coefficient:
- 6.56
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCCC1C2C(C3CCCC3)CCC2CC1
- Type:
- log Pow
- Partition coefficient:
- 7.16
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCCC1C2C(C(CCC)CC)CCC2CC1
- Type:
- log Pow
- Partition coefficient:
- 7.92
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CC1CC(CC(CCC2CCCC2)CCC)CC1
- Type:
- log Pow
- Partition coefficient:
- 10.79
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCC(CCC1C(CCC2C(C)CCCC2)CCCC1)CCC
- Type:
- log Pow
- Partition coefficient:
- 13.25
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCC(CCCC1C(CCC2C(CCCCCC)CCCC2)CCCC1)CCC
- Type:
- log Pow
- Partition coefficient:
- 13.13
- Remarks on result:
- not measured/tested
- Remarks:
- C(=O)(O)CCCCCCC1C(CCC2C(CCCC3CCCCC3)CCCC2)CCCC1
- Type:
- log Pow
- Partition coefficient:
- 12.23
- Remarks on result:
- not measured/tested
- Remarks:
- O=C(O)CCCCC(CC)CCC1CC2CCCC3CC(CCC(CC)CC)CC(C1)C23
- Type:
- log Pow
- Partition coefficient:
- 11.81
- Remarks on result:
- not measured/tested
- Remarks:
- O=C(O)CCCC(CCC)CCCC1CCC2CC(CCC2C1)CC3CCCC(C)C3
- Details on results:
- The examples assessed above do represent constituents in the range from C6 - C30 congeners of acids with 1 - 4 cycloalcyl moieties. Thus, they represent a wide range of possible constituents, knowingly that the average range of carbon numbers is more likely in the 10 - 15 range, making up ~ 90% by weight with a log Pow of ~ 3.7 - ~ 6.
- Conclusions:
- The EPI Suite (US EPA) Version 4.1 model KOWWIN v1.68 (September 2010) estimated the Log Kow to be in the range of mainly 3.7 - 6 for C10 - C15.
- Executive summary:
The log Pow was estimated with KOWWIN version 1.68. This QSAR model is included in the EpiSuite programs developed by Syracuse Research Corporation for US-EPA. The calculated log Pow for different structures of naphthenic acids ranges from 2.05 to 13.25, for smaller and larger molecules respectively (carbon number range from 6 - 30).
The most prominent group of naphthenic acids has 10 to 15 carbon numbers, for this group the logPow has a range from 3.7 to 6.0.
- Endpoint:
- partition coefficient
- Type of information:
- read-across from supporting substance (structural analogue or surrogate)
- Adequacy of study:
- supporting study
- Reliability:
- 4 (not assignable)
- Rationale for reliability incl. deficiencies:
- secondary literature
- Justification for type of information:
- Data widely used worldwide - regularly reviewed (last review July 22nd 2015, last update July 1st 2014)
- Guideline:
- other: Calculated value, no reference reported
- GLP compliance:
- not specified
- Type of method:
- other: calculated
- Specific details on test material used for the study:
- Not specified in NIOSH report
- Analytical method:
- other: calculated
- Type:
- log Pow
- Partition coefficient:
- >= 5
- Remarks on result:
- other: derived by calculation
- Conclusions:
- The log Pow of naphthenic acids is reported as >= 5 (calculated) in the NIOSH, International Chemical Safety Cards (ICSC) # 1654
Referenceopen allclose all
Description of key information
The log Pow was estimated for the various naphthenic acid anions, formed in aqueous environment, with KOWWIN version 1.68. This QSAR model is included in the EpiSuite programs developed by Syracuse Research Corporation for US-EPA. The calculated log Pow for different structures of naphthenic acids ranges from 2.05 to 13.25, for smaller and larger molecules respectively (carbon number range from 6 - 30). The most prominent group of naphthenic acids in bismuth naphthenates has 10 to 15 carbon numbers, for this group the logPow has a range from 3.7 to 6.0. A weighted average of ~ 5 is used for hazard and risk assessment.
Key value for chemical safety assessment
- Log Kow (Log Pow):
- 5
- at the temperature of:
- 20 °C
Additional information
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.
Reproduction or further distribution of this information may be subject to copyright protection. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner.
