NP-MRD: Showing NP-Card for Ascorbyl stearate (NP0337711)

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Record Information

Version

2.0

Created at

2024-09-11 12:03:00 UTC

Updated at

2024-09-11 12:03:00 UTC

NP-MRD ID

NP0337711

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ascorbyl stearate

Description

Ascorbyl stearate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ascorbyl stearate was first documented in 2005 (PMID: 16154915). Based on a literature review a significant number of articles have been published on Ascorbyl stearate (PMID: 37084831) (PMID: 30863699) (PMID: 29291843) (PMID: 29273564) (PMID: 27919962) (PMID: 18225552).

Structure

MOL SDF PDB SMILES InChI

  Mrv2104 05262314352D          

 31 31  0  0  0  0            999 V2000
   -7.3272   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6127   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8983   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1838   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7549   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8970   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5320   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2464   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9609   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6754   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3899   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1043   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2477   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9622   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4304   13.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9824   13.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6767   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5699   14.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9622   12.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   14.2961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6019   12.3285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8029   13.6624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9054   15.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333   13.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7629   14.2915    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  1  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
 19 18  1  0  0  0  0
 20 17  1  0  0  0  0
 22 21  2  0  0  0  0
 23 19  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  2  0  0  0  0
 27 21  1  0  0  0  0
 28 22  1  0  0  0  0
 29 24  2  0  0  0  0
 30 18  1  0  0  0  0
 30 20  1  0  0  0  0
 31 23  1  0  0  0  0
 31 24  1  0  0  0  0
M  END

  Mrv2104 05262314352D          

 31 31  0  0  0  0            999 V2000
   -7.3272   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6127   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8983   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1838   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4693   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7549   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8970   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5320   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2464   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9609   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6754   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3899   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1043   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2477   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9622   13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4304   13.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9824   13.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6767   13.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5699   14.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9622   12.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8188   14.2961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6019   12.3285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8029   13.6624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9054   15.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5333   13.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7629   14.2915    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  1  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
 19 18  1  0  0  0  0
 20 17  1  0  0  0  0
 22 21  2  0  0  0  0
 23 19  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  2  0  0  0  0
 27 21  1  0  0  0  0
 28 22  1  0  0  0  0
 29 24  2  0  0  0  0
 30 18  1  0  0  0  0
 30 20  1  0  0  0  0
 31 23  1  0  0  0  0
 31 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337711

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1/C24H42O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(26)30-18-19(25)23-21(27)22(28)24(29)31-23/h19,23,25,27-28H,2-18H2,1H3

> <INCHI_KEY>
LITUBCVUXPBCGA-UHFFFAOYNA-N

> <FORMULA>
C24H42O7

> <MOLECULAR_WEIGHT>
442.593

> <EXACT_MASS>
442.293053692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.9147759032197

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl octadecanoate

> <JCHEM_LOGP>
5.896632356666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.592430241620574

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.24973622689256

> <JCHEM_PKA_STRONGEST_BASIC>
-3.568905785975451

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
119.82549999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
ascorbyl stearate

> <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     -13.677  24.376   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.344  25.146   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.010  24.376   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.676  25.146   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.343  24.376   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.009  25.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.675  24.376   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.342  25.146   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.008  24.376   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.674  25.146   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.341  24.376   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.993  25.146   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.327  24.376   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.660  25.146   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.994  24.376   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.328  25.146   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.661  24.376   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.662  25.146   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.996  24.376   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.995  25.146   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.737  24.520   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.767  25.664   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.330  25.146   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.997  26.998   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.996  22.836   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.995  26.686   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      16.057  23.013   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      18.299  25.503   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      16.623  28.405   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.329  24.376   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      14.491  26.677   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   20                                                       
CONECT   18   19   30                                                       
CONECT   19   18   23   25                                                  
CONECT   20   17   26   30                                                  
CONECT   21   22   23   27                                                  
CONECT   22   21   24   28                                                  
CONECT   23   19   21   31                                                  
CONECT   24   22   29   31                                                  
CONECT   25   19                                                            
CONECT   26   20                                                            
CONECT   27   21                                                            
CONECT   28   22                                                            
CONECT   29   24                                                            
CONECT   30   18   20                                                       
CONECT   31   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Value	Source
Ascorbyl stearic acid	Generator

Chemical Formula

C₂₄H₄₂O₇

Average Mass

442.5930 Da

Monoisotopic Mass

442.29305 Da

IUPAC Name

2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl octadecanoate

Traditional Name

ascorbyl stearate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O

InChI Identifier

InChI=1/C24H42O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(26)30-18-19(25)23-21(27)22(28)24(29)31-23/h19,23,25,27-28H,2-18H2,1H3

InChI Key

LITUBCVUXPBCGA-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Enoate ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Enediol
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	5.9	ChemAxon
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	119.83 m³·mol⁻¹	ChemAxon
Polarizability	52.91 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ascorbyl stearate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mohammed M, Ibrahim UH, Aljoundi A, Omolo CA, Devnarain N, Gafar MA, Mocktar C, Govender T: Enzyme-responsive biomimetic solid lipid nanoparticles for antibiotic delivery against hyaluronidase-secreting bacteria. Int J Pharm. 2023 Jun 10;640:122967. doi: 10.1016/j.ijpharm.2023.122967. Epub 2023 Apr 20. [PubMed:37084831 ]
Mane SD, Kamatham AN: Ascorbyl stearate stimulates cell death by oxidative stress-mediated apoptosis and autophagy in HeLa cervical cancer cell line in vitro. 3 Biotech. 2019 Mar;9(3):115. doi: 10.1007/s13205-019-1628-5. Epub 2019 Mar 2. [PubMed:30863699 ]
Fathi F, Mohammadzadeh-Aghdash H, Sohrabi Y, Dehghan P, Ezzati Nazhad Dolatabadi J: Kinetic and thermodynamic studies of bovine serum albumin interaction with ascorbyl palmitate and ascorbyl stearate food additives using surface plasmon resonance. Food Chem. 2018 Apr 25;246:228-232. doi: 10.1016/j.foodchem.2017.11.023. Epub 2017 Nov 8. [PubMed:29291843 ]
Mane SD, Kamatham AN: Ascorbyl stearate and ionizing radiation potentiate apoptosis through intracellular thiols and oxidative stress in murine T lymphoma cells. Chem Biol Interact. 2018 Feb 1;281:37-50. doi: 10.1016/j.cbi.2017.12.028. Epub 2017 Dec 19. [PubMed:29273564 ]
Mane SD, Thoh M, Sharma D, Sandur SK, Naidu KA: Ascorbyl Stearate Promotes Apoptosis Through Intrinsic Mitochondrial Pathway in HeLa Cancer Cells. Anticancer Res. 2016 Dec;36(12):6409-6417. doi: 10.21873/anticanres.11238. [PubMed:27919962 ]
Naidu KA, Fang Q, Naidu KA, Cheng JQ, Nicosia SV, Coppola D: P53 enhances ascorbyl stearate-induced G2/M arrest of human ovarian cancer cells. Anticancer Res. 2007 Nov-Dec;27(6B):3927-34. [PubMed:18225552 ]
Fang Q, Naidu KA, Naidu KA, Zhao H, Sun M, Dan HC, Nasir A, Kaiser HE, Cheng JQ, Nicosia SV, Coppola D: Ascorbyl stearate inhibits cell proliferation and tumor growth in human ovarian carcinoma cells by targeting the PI3K/AKT pathway. Anticancer Res. 2006 Jan-Feb;26(1A):203-9. [PubMed:16475700 ]
Elmore AR: Final report of the safety assessment of L-Ascorbic Acid, Calcium Ascorbate, Magnesium Ascorbate, Magnesium Ascorbyl Phosphate, Sodium Ascorbate, and Sodium Ascorbyl Phosphate as used in cosmetics. Int J Toxicol. 2005;24 Suppl 2:51-111. doi: 10.1080/10915810590953851. [PubMed:16154915 ]

Showing NP-Card for Ascorbyl stearate (NP0337711)

MOL for NP0337711 (Ascorbyl stearate)

3D MOL for NP0337711 (Ascorbyl stearate)

3D SDF for NP0337711 (Ascorbyl stearate)

3D-SDF for NP0337711 (Ascorbyl stearate)

PDB for NP0337711 (Ascorbyl stearate)

3D PDB for NP0337711 (Ascorbyl stearate)

SMILES for NP0337711 (Ascorbyl stearate)

INCHI for NP0337711 (Ascorbyl stearate)

Structure for NP0337711 (Ascorbyl stearate)

3D Structure for NP0337711 (Ascorbyl stearate)