NP-MRD: Showing NP-Card for fostex (NP0284328)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 11:58:51 UTC

Updated at

2022-09-09 11:58:52 UTC

NP-MRD ID

NP0284328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fostex

Description

Benzoyl peroxide, also known as benzoyl or lucidol, belongs to the class of organic compounds known as benzoyl peroxides. These are organic compounds containing two benzoyl groups O-linked to each other via a peroxide group. Their skeleton has the general formula [C6H5C(O)]2O2. Benzoyl peroxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzoyl peroxide is a mild and benzaldehyde tasting compound. Outside of the human body, Benzoyl peroxide has been detected, but not quantified in, cereals and cereal products and milk and milk products. This could make benzoyl peroxide a potential biomarker for the consumption of these foods. In medicine, benzoyl peroxide is used as a topical treatment for acne, either in combination with antibiotics or as a single agent. Benzoyl peroxide acts as an antibacterial, irritant, keratolytic, comedolytic, and anti-inflammatory agent when applied topically to the human epithelium. Benzoyl peroxide also increases the turnover rate of epithelial cells, thereby peeling the skin and promoting the resolution of comedones. Alternatively, the radicals may gain a hydrogen atom from biomolecules forming the more stable and primary metabolite, benzoic acid. fostex is found in Arabidopsis thaliana and Onychium lucidum. fostex was first documented in 1983 (PMID: 6222704). Benzoyl peroxide undergoes metabolism by keratinocytes in the epidermis (PMID: 12012746) (PMID: 4028702) (PMID: 8204465) (PMID: 15481998).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061306192D          

 18 19  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(OOC(=O)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O4/c15-13(11-7-3-1-4-8-11)17-18-14(16)12-9-5-2-6-10-12/h1-10H

> <INCHI_KEY>
OMPJBNCRMGITSC-UHFFFAOYSA-N

> <FORMULA>
C14H10O4

> <MOLECULAR_WEIGHT>
242.2268

> <EXACT_MASS>
242.057908808

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.15778938018316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
benzoyl benzenecarboperoxoate

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
3.946932388

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.169419788005589

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
64.77320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fostex

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10    6   12                                                       
CONECT   11    7    8   13                                                  
CONECT   12    9   10   14                                                  
CONECT   13   11   15   17                                                  
CONECT   14   12   16   18                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   14   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Bepio	Kegg
Abcat 40	HMDB
Abcure S-40-25	HMDB
Acetoxyl	HMDB
AcetOxyl 2.5 and 5	HMDB
Acnegel	HMDB
Akneroxid 5	HMDB
Akneroxid L	HMDB
Akneroxide L	HMDB
Aksil 5	HMDB
Asidopan	HMDB
Aztec benzoyl peroxide-70-77	HMDB
Aztec benzoyl peroxide-dry	HMDB
Aztec bpo	HMDB
Benbel c	HMDB
Benox 50	HMDB
Benoxyl	HMDB
Benoxyl (5&10) lotion	HMDB
Benzac	HMDB
Benzac W	HMDB
Benzagel	HMDB
Benzagel 10	HMDB
Benzaknen	HMDB
Benzaknew	HMDB
Benzamycin	HMDB
Benzashave	HMDB
Benzoic acid, peroxide	HMDB
Benzol peroxide	HMDB
Benzoperoxide	HMDB
Benzoyl	HMDB
Benzoyl peroide	HMDB
Benzoyl peroxide (luperox(R) a70S)	HMDB
Benzoyl peroxide (luperox(R) a75)	HMDB
Benzoyl peroxide (luperox(R) a75fp)	HMDB
Benzoyl peroxide (luperox(R) a98)	HMDB
Benzoyl peroxide(usan)	HMDB
Benzoyl peroxide, blend in dibutyl phthalate	HMDB
Benzoyl peroxide, blend in tricresyl phosphate	HMDB
Benzoyl peroxide, usan	HMDB
Benzoyl superoxide	HMDB
Benzoylperoxid	HMDB
Benzoylperoxyde	HMDB
BPO	HMDB
Brevoxyl	HMDB
Cadat bpo	HMDB
Cadet	HMDB
Cadet bpo-70W	HMDB
Cadox	HMDB
Cadox 40E	HMDB
Cadox b	HMDB
Cadox b 40E	HMDB
Cadox b 50P	HMDB
Cadox b 70W	HMDB
Cadox b-CH 50	HMDB
Cadox bpo-w40	HMDB
Cadox BS	HMDB
Cadox bta	HMDB
Cadox BTW-50	HMDB
Chaloxyd BP 50FT	HMDB
Clear by design	HMDB
Clearasil antibacterial acne lotion	HMDB
Clearasil benzoyl peroxide lotion	HMDB
Clearasil BP acne treatment	HMDB
Debroxide	HMDB
Dermoxyl	HMDB
Desanden	HMDB
Desquam e	HMDB
Desquam X	HMDB
Desquam-X	HMDB
Dibenzoylperoxid	HMDB
Dibenzoylperoxyde	HMDB
Diphenylglyoxal peroxide	HMDB
Diphenylglyoxal superoxide	HMDB
Diphenylperoxyanhydride	HMDB
DRY and clear	HMDB
Duresthin 5	HMDB
Eloxyl	HMDB
Epi clear antiseptic lotion	HMDB
Epi-clear	HMDB
Florox	HMDB
Fostex bpo	HMDB
Garox	HMDB
Incidol	HMDB
Loroxide	HMDB
Lucidol	HMDB
Lucidol (peroxide)	HMDB
Lucidol 50P	HMDB
Lucidol 75fp	HMDB
Lucidol b 50	HMDB
Lucidol g 20	HMDB
Lucidol GS	HMDB
Lucidol KL 50	HMDB
Lucidol RM	HMDB
Lucidol-70	HMDB
Lucidol-78	HMDB
Lucilite	HMDB
Lucipal	HMDB
Luperco	HMDB
Luperco a	HMDB
Luperco aa	HMDB
Luperco ac	HMDB
Luperco afr	HMDB
Luperco afr-250	HMDB
Luperco ast	HMDB
Luperox a98	HMDB
Luperox FL	HMDB
Luzidol	HMDB
Mixture OF dibenzoyl peroxide and calcium sulfate	HMDB
Mixture OF dibenzoyl peroxide and calcium sulphate	HMDB
Mytolac	HMDB
Nayper b and bo	HMDB
Nayper bo	HMDB
Nericur	HMDB
Norox BZP-250	HMDB
Norox BZP-C-35	HMDB
Novadeiox	HMDB
Novadelox	HMDB
NSC 675	HMDB
Oxy 5	HMDB
Oxy wash	HMDB
Oxy-10 cover	HMDB
Oxy-5	HMDB
Oxy-L	HMDB
Oxylite	HMDB
Panoxyl	HMDB
Periygel	HMDB
Perossido di benzoile	HMDB
Peroxide, benzoyl	HMDB
Peroxide, dibenzoyl	HMDB
Peroxyde de benzoyle	HMDB
Peroxyderm	HMDB
Peroxydex	HMDB
Persa-gel	HMDB
Persadox	HMDB
Phisoac BP	HMDB
Preoxydex	HMDB
Presadox	HMDB
Quinolor compound	HMDB
Resdan akne	HMDB
Sanoxit	HMDB
Silica hydrogel	HMDB
Stri-dex b.p	HMDB
Stri-dex b.p.	HMDB
Sulfoxyl	HMDB
Superox	HMDB
Superox 744	HMDB
Superoxide, benzoyl	HMDB
Superoxide, diphenylglyoxal	HMDB
Thermaderm	HMDB
Topex	HMDB
Vanoxide	HMDB
Xerac	HMDB
Xerac BP	HMDB
Xerac BP 10	HMDB
Xerac BP 5	HMDB
Dibenzoyl peroxide	MeSH

Chemical Formula

C₁₄H₁₀O₄

Average Mass

242.2268 Da

Monoisotopic Mass

242.05791 Da

IUPAC Name

benzoyl benzenecarboperoxoate

Traditional Name

fostex

CAS Registry Number

Not Available

SMILES

O=C(OOC(=O)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H10O4/c15-13(11-7-3-1-4-8-11)17-18-14(16)12-9-5-2-6-10-12/h1-10H

InChI Key

OMPJBNCRMGITSC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	LOTUS Database	35616633
Onychium lucidum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoyl peroxides. These are organic compounds containing two benzoyl groups O-linked to each other via a peroxide group. Their skeleton has the general formula [C6H5C(O)]2O2.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoyl peroxides

Direct Parent

Benzoyl peroxides

Alternative Parents

Substituents

Benzoyl peroxide
Peroxybenzoate
Benzoic acid or derivatives
Benzoyl
Dicarboxylic acid or derivatives
Peroxycarboxylic acid or derivatives
Carboxylic acid salt
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbonyl compound (CHEBI:82405 )

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	2.75	ALOGPS
logP	3.95	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.77 m³·mol⁻¹	ChemAxon
Polarizability	24.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0032040

DrugBank ID

DB09096

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008743

KNApSAcK ID

Not Available

Chemspider ID

6919

KEGG Compound ID

C19346

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzoyl peroxide

METLIN ID

Not Available

PubChem Compound

7187

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Welch SL: Oral toxicity of topical preparations. Vet Clin North Am Small Anim Pract. 2002 Mar;32(2):443-53, vii. doi: 10.1016/s0195-5616(01)00005-5. [PubMed:12012746 ]
Nacht S, Gans EH, McGinley KJ, Kligman AM: Comparative activity of benzoyl peroxide and hexachlorophene. In vivo studies against propionibacterium acnes in humans. Arch Dermatol. 1983 Jul;119(7):577-9. [PubMed:6222704 ]
Angelini G, Vena GA, Meneghini CL: Allergic contact dermatitis to some medicaments. Contact Dermatitis. 1985 May;12(5):263-9. doi: 10.1111/j.1600-0536.1985.tb01133.x. [PubMed:4028702 ]
Hegemann L, Toso SM, Kitay K, Webster GF: Anti-inflammatory actions of benzoyl peroxide: effects on the generation of reactive oxygen species by leucocytes and the activity of protein kinase C and calmodulin. Br J Dermatol. 1994 May;130(5):569-75. doi: 10.1111/j.1365-2133.1994.tb13101.x. [PubMed:8204465 ]
Dreno B: Topical antibacterial therapy for acne vulgaris. Drugs. 2004;64(21):2389-97. doi: 10.2165/00003495-200464210-00002. [PubMed:15481998 ]
LOTUS database [Link]

Showing NP-Card for fostex (NP0284328)

MOL for NP0284328 (fostex)

3D MOL for NP0284328 (fostex)

3D SDF for NP0284328 (fostex)

3D-SDF for NP0284328 (fostex)

PDB for NP0284328 (fostex)

3D PDB for NP0284328 (fostex)

SMILES for NP0284328 (fostex)

INCHI for NP0284328 (fostex)

Structure for NP0284328 (fostex)

3D Structure for NP0284328 (fostex)