NP-MRD: Showing NP-Card for Sorbitan oleate (NP0336578)

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Record Information

Version

2.0

Created at

2024-09-11 06:56:35 UTC

Updated at

2024-09-11 06:56:35 UTC

NP-MRD ID

NP0336578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sorbitan oleate

Description

Sorbitan oleate was first documented in 2010 (PMID: 20942432). Based on a literature review a significant number of articles have been published on Sorbitan oleate (PMID: 37546220) (PMID: 37447500) (PMID: 37293575) (PMID: 35690013) (PMID: 35403530) (PMID: 35199120).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262309282D          

 30 30  0  0  0  0            999 V2000
   -7.5906    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8761    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1617    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4472    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7327    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3038    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5893    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8748    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4459    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2686    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9830    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6975    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4120    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1264    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8409    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3065    7.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9843    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7190    8.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6988    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5554    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1669    8.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4133    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5395    8.2493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6988    9.6781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5554    7.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3385    9.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2699    8.8531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4995    7.6202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 17  1  0  0  0  0
 23 20  1  0  0  0  0
 24 21  1  0  0  0  0
 24 23  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  2  0  0  0  0
 28 23  1  0  0  0  0
 29 19  1  0  0  0  0
 29 22  1  0  0  0  0
 30 18  1  0  0  0  0
 30 24  1  0  0  0  0
M  END


  Mrv2104 05262309282D          

 30 30  0  0  0  0            999 V2000
   -7.5906    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8761    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1617    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4472    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7327    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3038    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5893    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8748    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4459    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2686    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9830    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6975    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4120    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1264    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8409    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3065    7.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9843    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7190    8.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6988    8.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5554    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1669    8.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4133    8.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5395    8.2493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6988    9.6781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5554    7.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3385    9.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2699    8.8531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4995    7.6202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 17  1  0  0  0  0
 23 20  1  0  0  0  0
 24 21  1  0  0  0  0
 24 23  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  2  0  0  0  0
 28 23  1  0  0  0  0
 29 19  1  0  0  0  0
 29 22  1  0  0  0  0
 30 18  1  0  0  0  0
 30 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC\C=C\CCCCCCCC(=O)OCC(O)C1OCC(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C24H44O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(27)29-19-21(26)24-23(28)20(25)18-30-24/h9-10,20-21,23-26,28H,2-8,11-19H2,1H3/b10-9+

> <INCHI_KEY>
NWGKJDSIEKMTRX-MDZDMXLPNA-N

> <FORMULA>
C24H44O6

> <MOLECULAR_WEIGHT>
428.61

> <EXACT_MASS>
428.313789137

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.79611900185466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyoxolan-2-yl)-2-hydroxyethyl (9E)-octadec-9-enoate

> <JCHEM_LOGP>
4.879954299333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.472613395945105

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.746293780566992

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5225969661410432

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
118.80349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
sorbitan monooleate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0     -14.169  16.526   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.835  15.756   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.502  16.526   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.168  15.756   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.834  16.526   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.501  15.756   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.167  16.526   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.833  15.756   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.500  16.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.166  15.756   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.832  16.526   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.501  15.756   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.835  16.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.169  15.756   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.502  16.526   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.836  15.756   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.170  16.526   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.505  13.904   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.171  15.756   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.275  15.238   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.504  16.526   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.503  15.756   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.245  16.382   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.838  15.756   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      17.807  15.399   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      12.504  18.066   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.503  14.216   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      15.565  17.889   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.837  16.526   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.999  14.224   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                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   22                                                       
CONECT   18   20   30                                                       
CONECT   19   21   29                                                       
CONECT   20   18   23   25                                                  
CONECT   21   19   24   26                                                  
CONECT   22   17   27   29                                                  
CONECT   23   20   24   28                                                  
CONECT   24   21   23   30                                                  
CONECT   25   20                                                            
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28   23                                                            
CONECT   29   19   22                                                       
CONECT   30   18   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

View in JSmol

Synonyms

Value	Source
Sorbitan oleic acid	Generator

Chemical Formula

C₂₄H₄₄O₆

Average Mass

428.6100 Da

Monoisotopic Mass

428.31379 Da

IUPAC Name

2-(3,4-dihydroxyoxolan-2-yl)-2-hydroxyethyl (9E)-octadec-9-enoate

Traditional Name

sorbitan monooleate

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C\CCCCCCCC(=O)OCC(O)C1OCC(O)C1O

InChI Identifier

InChI=1/C24H44O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(27)29-19-21(26)24-23(28)20(25)18-30-24/h9-10,20-21,23-26,28H,2-8,11-19H2,1H3/b10-9+

InChI Key

NWGKJDSIEKMTRX-MDZDMXLPNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	4.88	ChemAxon
pKa (Strongest Acidic)	12.75	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	118.8 m³·mol⁻¹	ChemAxon
Polarizability	51.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sorbitan monooleate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shadmani N, Gohari S, Kadkhodamanesh A, Ghaderinia P, Hassani M, Sharifyrad M: The synthesis and development of poly(epsilon-caprolactone) conjugated polyoxyethylene sorbitan oleate-based micelles for curcumin drug release: an in vitro study on breast cancer cells. RSC Adv. 2023 Aug 4;13(34):23449-23460. doi: 10.1039/d3ra03660j. eCollection 2023 Aug 4. [PubMed:37546220 ]
Moldovan A, Cuc S, Prodan D, Rusu M, Popa D, Taut AC, Petean I, Bombos D, Doukeh R, Nemes O: Development and Characterization of Polylactic Acid (PLA)-Based Nanocomposites Used for Food Packaging. Polymers (Basel). 2023 Jun 28;15(13):2855. doi: 10.3390/polym15132855. [PubMed:37447500 ]
Chaiyana W, Jiamphun S, Bezuidenhout S, Yeerong K, Krueathanasing N, Thammasorn P, Jittasai P, Tanakitvanicharoen S, Tima S, Anuchapreeda S: Enhanced Cosmeceutical Potentials of the Oil from Gryllus bimaculatus de Geer by Nanoemulsions. Int J Nanomedicine. 2023 Jun 3;18:2955-2972. doi: 10.2147/IJN.S406864. eCollection 2023. [PubMed:37293575 ]
Chenwei L, Liang Y, Chenru Z, Zhiyuan W, Mingzhong L: Effects of hydrate inhibitors on the adhesion strengths of sintered hydrate deposits on pipe walls. J Colloid Interface Sci. 2022 Oct 15;624:593-601. doi: 10.1016/j.jcis.2022.06.004. Epub 2022 Jun 6. [PubMed:35690013 ]
Tuntiyasawasdikul S, Sripanidkulchai B: Curcuma comosa loaded transfersomal gel for transdermal application: formulation, in vitro and in vivo evaluation. Drug Dev Ind Pharm. 2021 Nov;47(11):1824-1834. doi: 10.1080/03639045.2022.2064486. Epub 2022 Apr 21. [PubMed:35403530 ]
Lee CK, Zhang S, Venkatesan G, Irsan, Chong SY, Wang JW, Goh WJ, Panczyk T, Tay YZ, Hu J, Ng WK, Wacker MG, Toh WS, Pastorin G: Enhanced skin penetration of berberine from proniosome gel attenuates pain and inflammation in a mouse model of osteoarthritis. Biomater Sci. 2022 Mar 29;10(7):1752-1764. doi: 10.1039/d1bm01733k. [PubMed:35199120 ]
Shen Y, Xia Y, Yang E, Ye Z, Ding Y, Tu J, Zhang Y, Xu P: A polyoxyethylene sorbitan oleate modified hollow gold nanoparticle system to escape macrophage phagocytosis designed for triple combination lung cancer therapy via LDL-R mediated endocytosis. Drug Deliv. 2020 Dec;27(1):1342-1359. doi: 10.1080/10717544.2020.1822459. [PubMed:32964732 ]
Sommer E, Neubert RHH, Mentel M, Tuchscherer B, Mrestani Y, Wohlrab J: Dermal peptide delivery using enhancer molecules and colloidal carrier systems. Part III: Tetrapeptide GEKG. Eur J Pharm Sci. 2018 Nov 1;124:137-144. doi: 10.1016/j.ejps.2018.08.034. Epub 2018 Aug 27. [PubMed:30165235 ]
Poomanee W, Chaiyana W, Randall Wickett R, Leelapornpisid P: Stability and solubility improvement of Sompoi (Acacia concinna Linn.) pod extract by topical microemulsion. Asian J Pharm Sci. 2017 Jul;12(4):386-393. doi: 10.1016/j.ajps.2017.03.001. Epub 2017 Mar 8. [PubMed:32104350 ]
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Showing NP-Card for Sorbitan oleate (NP0336578)

MOL for NP0336578 (Sorbitan oleate)

3D MOL for NP0336578 (Sorbitan oleate)

3D SDF for NP0336578 (Sorbitan oleate)

3D-SDF for NP0336578 (Sorbitan oleate)

PDB for NP0336578 (Sorbitan oleate)

3D PDB for NP0336578 (Sorbitan oleate)

SMILES for NP0336578 (Sorbitan oleate)

INCHI for NP0336578 (Sorbitan oleate)

Structure for NP0336578 (Sorbitan oleate)

3D Structure for NP0336578 (Sorbitan oleate)