NP-MRD: Showing NP-Card for (-)-cis-9,10-Epoxystearic acid (NP0050307)

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Record Information

Version

2.0

Created at

2022-04-27 20:52:14 UTC

Updated at

2022-04-27 20:52:14 UTC

NP-MRD ID

NP0050307

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-cis-9,10-Epoxystearic acid

Description

(9S,10R)-epoxyoctadecanoic acid, also known as (9S,10R)-epoxystearate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. (-)-cis-9,10-Epoxystearic acid is found in Fusarium oxysporum and Shorea robusta. Based on a literature review very few articles have been published on (9S,10R)-epoxyoctadecanoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222522D          

 21 21  0  0  1  0            999 V2000
   -9.2072   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4927   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7783   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0638   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3493   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4914   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6664   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0789   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050307

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC[C@H]1O[C@H]1CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h16-17H,2-15H2,1H3,(H,19,20)/t16-,17+/m1/s1

> <INCHI_KEY>
IMYZYCNQZDBZBQ-SJORKVTESA-N

> <FORMULA>
C18H34O3

> <MOLECULAR_WEIGHT>
298.467

> <EXACT_MASS>
298.250794955

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.22256267856366

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[(2S,3R)-3-octyloxiran-2-yl]octanoic acid

> <ALOGPS_LOGP>
6.55

> <JCHEM_LOGP>
5.845801546

> <ALOGPS_LOGS>
-5.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615325352103512

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2025601909528545

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
85.8065

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.06e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9S,10R-epoxy-stearic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0     -17.187  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.853  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.519  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.186  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.852  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.518  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.185  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.851  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.517  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.977  -1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.747  -2.667   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.976  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.357  -1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.691  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.025  -1.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.358  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.692  -1.334   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.026  -0.564   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.692  -2.874   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    9                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
(9S,10R)-Epoxystearic acid	ChEBI
(9S,10R)-Epoxystearate	Generator
(9S,10R)-Epoxyoctadecanoate	Generator

Chemical Formula

C₁₈H₃₄O₃

Average Mass

298.4670 Da

Monoisotopic Mass

298.25079 Da

IUPAC Name

8-[(2S,3R)-3-octyloxiran-2-yl]octanoic acid

Traditional Name

9S,10R-epoxy-stearic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCC[C@H]1O[C@H]1CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h16-17H,2-15H2,1H3,(H,19,20)/t16-,17+/m1/s1

InChI Key

IMYZYCNQZDBZBQ-SJORKVTESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusarium oxysporum	Fungi	KNApSAcK
Shorea robusta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Medium-chain fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Fatty acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Other Octadecanoids (LMFA02000001 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.55	ALOGPS
logP	5.85	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	85.81 m³·mol⁻¹	ChemAxon
Polarizability	38.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

106527

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119250

PDB ID

Not Available

ChEBI ID

138262

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-cis-9,10-Epoxystearic acid (NP0050307)

MOL for NP0050307 ((-)-cis-9,10-Epoxystearic acid)

3D MOL for NP0050307 ((-)-cis-9,10-Epoxystearic acid)

3D SDF for NP0050307 ((-)-cis-9,10-Epoxystearic acid)

3D-SDF for NP0050307 ((-)-cis-9,10-Epoxystearic acid)

PDB for NP0050307 ((-)-cis-9,10-Epoxystearic acid)

3D PDB for NP0050307 ((-)-cis-9,10-Epoxystearic acid)

SMILES for NP0050307 ((-)-cis-9,10-Epoxystearic acid)

INCHI for NP0050307 ((-)-cis-9,10-Epoxystearic acid)

Structure for NP0050307 ((-)-cis-9,10-Epoxystearic acid)

3D Structure for NP0050307 ((-)-cis-9,10-Epoxystearic acid)